90 Of The Best Movies To Stream On Prime Video In May
1.(500) Days of Summer (2009)
Perhaps the most outstanding thing about (500) Days of Summer — more than the incredible indie soundtrack, Zooey Deschanel's "manic pixie dream girl" rise to fame, and the fact that it makes every person walking through Ikea pretend that it is their dream house — is that every time you watch it, a different member of the romantic couple is the villain. Is Joseph Gordon-Levitt's Tom too idealistic, clingy, controlling, and unrealistic? Is Deschanel's Summer leading him on, afraid of commitment, and toying with his feelings? Everyone you ask has a different (VERY STRONG) opinion. The beauty of the script and performances, however, is that it accurately portrays an ill-fated relationship where neither party is the hero or the villain. They're just both people who at that time are not compatible, for whatever reason. You've just never seen it on film before.
Watch it on Prime Video.
2.A.I. Artificial Intelligence (2001)
As Steven Spielberg has been wracking up the Oscar nominations for his historical films like The Post, Bridge of Spies, Lincoln, and even this year's West Side Story remake, it can be easy to forget he started as a sci-fi savant. One of his most ambitious pieces of futuristic storytelling is this reimagining of Pinocchio in which The Sixth Sense's Haley Joel Osment plays a robot child who wants desperately to be a real boy. Osment offers an eery adorableness in the role as he stumbles upon a series of misadventures trying to unlock the secret to humanity. A robotic gigolo Jude Law joins him on part of the dangerous journey, and Meryl Streep arrives briefly for some voice work. If you've already polished off Close Encounters of the Third Kind and E.T. then this is your next step into the Spielberg-verse.
Watch it on Prime Video.
3.All the Old Knives (2022)
In the ongoing debate over which of the four Chrises is the best, this is certainly a strike in the favor of Mr. Pine. What could have easily been a run-of-the-mill spy thriller based on a novel (think Jack Reacher or Jack Ryan) is elevated by a creative storyline and unsurprisingly good performances by the all-star cast consisting of Pine, Thandiwe Newton, Laurence Fishburne, and Jonathan Pryce. Set over a sumptuous food-porn dinner (think Pig without the Nic Cage grunting), Pine and Newton discuss their days working in Vienna years earlier, where their relationship, as coworkers and lovers, disintegrated. After their CIA team botched a hostage situation that resulted in the deaths of an entire plane full of civilians, the pair moved on only to reconnect and attempt to unravel what exactly happened all those years ago. The film looks expensive, the mystery is compelling, and a series of twists will keep you on the edge of your seat. Chris's best work since he fell in that fountain in Princess Diaries 2.
Watch it on Prime Video.
4.Annette (2021)
Let me say right off the bat that this is NOT a film for everyone. The rock opera musical from French auteur Leos Carax (Holy Motors) performed well among the elite cinephiles present at its Cannes Film Festival premiere, but its polarizing, slightly obtuse nature will make it a difficult sit for many. Adam Driver plays an edgy stand-up comedian who falls in love with Marion Cotillard’s opera singer. While Driver and Cotillard throw the full force of their acting powers into the roles, to mesmerizing effect, the structure of the movie, mimicking that of an opera, is much slower than a traditional movie musical. For those in love with French cinema and looking for a challenge, however, this could be a rewarding way to spend an evening.
Watch it on Prime Video.
5.Armageddon (1998)
Sadly, Bruce Willis has recently stepped back from acting due to being diagnosed with aphasia, but if you love the actor as much as I do (Moonlighting, Die Hard, The Kid), then you'll want to revisit this classic. The highest-grossing film of 1998, the sci-fi disaster epic follows a group of deep-core drillers who get sent to stop a giant asteroid from obliterating Earth. It's an early Michael Bay film (before a group of Transformers took his family hostage and required him only to make movies starring Optimus Prime), and an early J.J. Abrams script, solidifying the pair as our sci-fi grandmasters for years to come. The film brought us "I Don't Want to Miss A Thing", landed four Oscar noms, and reminded the world that just because critics hate it (38% on Rotten Tomatoes), it can still be an incredible film.
Watch it on Prime Video.
6.*Baby Mama (2008)
Since their arrival on Saturday Night Live in 2000 and 2001, Tina Fey and Amy Poehler have become one of America's most iconic comedy duos. They manned the Weekend Update desk, they hosted the Golden Globes, they stole scenes in Mean Girls, and of course, they starred in this comedy about a woman and her surrogate. Both women are playing to their strengths here, with Fey taking on the role of uptight, single executive while Poehler plays the zany South Philly woman carrying her child. The pair have starred in several movies together since, but haven't quite matched the magic they attained here. If you love 30 Rock or Parks and Rec and haven't gone back to this film, then now is the time.
Watch it on Prime Video.
7.Beasts of the Southern Wild (2012)
Every now and then, a tiny indie film comes along that is so undeniable, it breaks through the ranks to Oscar success. In 2013, that film was this tiny whimsical drama about a girl named Hushpuppy growing up on an island in the Louisiana bayou (although she was never forced into a cave with tiny mice to steal diamonds). After winning the Best First Feature prize at Cannes, the film slowly picked up steam, enchanting audiences one by one until it arrived at the Oscars with Best Picture, Screenplay, Director, and Actress nominations in hand. The film also launched the career of Quvenzhané Wallis, who became the youngest actor ever nominated for Best Actress at the age of 9. At 9, I was still struggling to get a better part than Wise Man No. 2 at my church Christmas pageant.
Watch it on Prime Video.
8.*A Beautiful Mind (2001)
As someone who can BARELY do simple subtraction and still struggles to count without using his fingers, the math in this film is basically from another planet (and probably is even for those of you hoity-toity nerds in AP Calc). This Best Picture winner tells the story of Nobel Prize-winning mathematician John Nash, who struggled with paranoid schizophrenia while owning the titular "beautiful mind" for math. Both Russell Crowe (Nash) and Jennifer Connelly (who plays his wife) give tremendous performances that earned Oscar nominations (and a win in her case). Whether you're an Oscar completist, in a high school math class, or just someone looking for a compelling adult drama, this film is certainly an interesting one.
Watch it on Prime Video.
9.Being the Ricardos (2021)
"LUCY, I'M HOME!" And so is Amazon's new Lucille Ball biopic, which now resides on the tech giant's streaming platform. While the internet has expressed consternation about Academy Award winner Nicole Kidman's casting as the sitcom legend since the film's early stills appeared, there was no reason for concern. Kidman and Javier Bardem (who plays her husband, Desi Arnaz) combine just enough impression within their performances to make them believable without becoming caricatures. The Aaron Sorkin script is tight, focusing on the pair as they traverse a hectic week full of accusations of communism, cheating allegations, an unexpected pregnancy, inter-cast drama, and of course a full-episode production cycle. The film zips along, with Sorkin's dialogue leading the film to a propulsive and cathartic end. A rare Oscar contender that is as fun as it as good.
Watch it on Prime Video.
10.The Big Sick (2017)
So let’s say you dated a girl for five months and then she broke up with you. And then she went to the hospital and was put into a coma. And then her parents came and they knew you broke up. And then you just had to sit with them awkwardly in the waiting room because you did still care about the girl. Thus is the premise of The Big Sick, and also the real-life events surrounding the romance of the film's writers, Emily V. Gordon and Kumail Nanjiani (who is also the star). One of the best romantic comedies of the past decade, this film also examines interracial dating in a smart, nuanced way and is stacked with your comedy faves, including Holly Hunter, Ray Romano, and Bo Burnham (whose recent comedy special Inside is a masterpiece). Now is also a great time to watch The Big Sick, as ripped Nanjiani will be in Marvel’s Eternals this fall.
Watch it on Prime Video.
11.*Bill & Ted's Excellent Adventure (1989)
When my uncle suggested that we marathon all three Bill & Ted movies in one day during the pandemic, I was skeptical. An '80s slacker film? How good could it be? The answer is most excellent dude! Keanu Reeves and Alex Winter play a pair of lovable goofballs who travel back through time collecting famous historical figures for a high school project. It is a DELIGHT! The whole film holds up remarkably well (which cannot be said for most movies of the time), and the scene where the pair end up leaving their posse of historic besties at the San Dimas Mall is one for the ages (and one of the best mall scenes in cinema). Most outstanding! *plays air guitar*
Watch it on Prime Video.
12.*Black Swan (2010)
"It was perfect." — Me, lying on my couch having finished Black Swan feeling like I'd been stabbed in the stomach by a shard of glass. Natalie Portman is undeniable and Oscar-winning as the ambitious paranoid ballerina at the heart of Darren Aronofsky's psychological thriller. She's twirling (or at least her body double is). She's hallucinating. She's screaming at her mother and engaging in a lesbian romance. The Best Picture nominee is a twisty, delicious, haunting dance bolstered by great performances not only from Portman, but by the incomparable Barbara Hershey as her mother, Mila Kunis as her rival, and Winona Ryder as the aging star she replaces. Aronofsky has never recaptured the brilliance he brings here (not on Noah's Ark or in mother!'s house), so it will be interesting to see if he can regain momentum with this year's The Whale. Hopefully, there are fewer shots of gross feet in that one.
Watch it on Prime Video.
13.Bottle Shock (2008)
Once upon a time, I was home for the summer from college and rented this film from the library because I love Alan Rickman (Harry Potter, Robin Hood: Prince of Thieves, Sense and Sensibility; I could go on). I found the movie captivating and demanded the DVD for Christmas. Rickman stars as a snobbish connoisseur of French wine who decides to throw a competition between the lauded French wineries and the looked-down-upon Californian upstarts (the leads of whom are Bill Pullman and Chris Pine). Rickman is an absolute delight, and I (someone who buys $4 watermelon rosé from Trader Joes) was mesmerized by the true story that put Napa Valley on the map in the ’70s. Perhaps uncork a bottle of wine and settle in for the evening?
Watch it on Prime Video.
14.*Bride Wars (2009)
"Call me dreamcatcher. I'll answer." You can also call me an Anne Hathaway superfan (I've seen every single one of her movies) and a Bride Wars apologist. Don't let the 11% Rotten Tomatoes score deceive you — this Kate Hudson–Annie two-hander is a hoot. It's a campy sendup of bridezillas, with the pair resorting to Home Alone–level pranks to try to ruin the other's wedding. Candice Bergen, Casey Wilson, and Kristen Johnston show up in hilarious bit roles, and Chris Pratt was perfecting his creepy, overly possessive partner bit here long before his cringe IG post. Also, catch me doing "sprockets" on every dance floor from now to eternity.
Watch it on Prime Video.
15.Brittany Runs a Marathon (2019)
As somewhat of a marathon expert (I’ve written a whole book about the sport), I can personally attest to the tremendous amount of work that goes into running 26.2 miles, as well as the euphoric emotional payoff of finishing. This Jillian Bell film (based on a true story) follows Brittany as she signs up for the New York City Marathon in an attempt to get her life back on track. The heartwarming comedy also stars Michaela Watkins (Search Party) and Utkarsh Ambudkar (Pitch Perfect) and is the first feature film to actually shoot on location during the marathon. Watching Brittany finish her race is incredibly inspiring and will make you want to sign up for a marathon as well.
Watch it on Prime Video.
16.*Call Me By Your Name (2017)
Famously, this film has one of the Best Original Songs of the 21st Century in "Mystery of Love" by Sufjan Stevens, and that alone is enough reason to watch this film. Luckily, this Best Picture nominee from Luca Guadagnino has plenty of other wonders to recommend it as well. There are the beautiful landscape shots of the Italian countryside, and the many, many, many pairs of wonderful short shorts. There's the queer coming-of-age at its center. And then, of course, this is the film that introduced the world to Timothée Chalamet (unless of course, you remember him from being the Vice President's bratty son in Homeland). I shall skip over the Armie Hammer of it all, and instead remind you that it also includes one of the best end credit scenes involving Chalamet just weeping into the camera. Such a lovely film. I just wanna open my mouth and swallow the whole thing (as one might do with a peach).
Watch it on Prime Video.
17.Cast Away (2000)
Survivor - Jeff Probst + Tom Hanks's Oscar performance + Christian Bale weight loss transformation - Christian Bale + two iconic product placement deals = Cast Away. The film focuses on a FedEx employee (SO MUCH FEDEX HERE) who becomes stranded on a deserted island with nothing more than the contents of some salvaged mail and his wits to keep him alive. Hanks does some of his best work as the charming dad-bod businessman turned wiry island wild man. Of course, the most memorable part of the film is Hank's relationship with a volleyball named Wilson (product placement number two), whom he bonds with deeply. The Wilson raft scene alone is enough reason to watch this film. Also, it changed the way I think about ice forever.
Watch it on Prime Video.
18.Cold War (2018)
The first time I tried to see Cold War in theaters, I had to leave 10 minutes in because the man sitting behind me said he’d found bedbugs in his chair. Nevertheless! I had such high hopes for the movie that I booked a ticket at a different theater the next day (after nuking my clothes in the dryer and scrubbing down in the shower), and I was not disappointed. This Oscar-nominated Polish film from Pawel Pawlikowski follows the star-crossed 20-year romantic saga of Zula and Wiktor during the Cold War. Shot in stark black and white, the story is as beautiful as it is heartbreaking. A romance for the ages.
Watch it on Prime Video.
19.The Color of Money (1986)
We got plenty of sports movies focused on basketball, football, and baseball. Hell, we've even got a decent amount of films about tennis, surfing, and skateboarding. But pool? As in billiards? Really there are only two (the other, The Hustler), and they both star Paul Newman as Fast Eddie Felson, a hustler in the game of 9-ball pool. In the second installment, a retired Felson meets up with a young Tom Cruise (Vincent Lauria), deciding to back him on a string of billiards shakedowns. In his Oscar-winning performance here, however, Newman plays a man unable to stay on the sidelines and desperate for one last chance at cue ball-directed glory. The film is a fascinating look into the world of competitive pool (which I assume you don't know much about), a masterclass in acting, and a great young Tom Cruise performance where he isn't in the military. Rack 'em! (That's something pool players say, right?)
Watch it on Prime Video.
20.*Crazy Heart (2009)
If you watched and loved Maggie Gyllenhaal's directorial debut, The Lost Daughter, and want more of her where she's not just screaming "Harvey," then might I suggest her Oscar-nominated film? Here she plays a divorced journalist who begins a relationship with an alcoholic country musician played by Jeff Bridges (who won the Oscar). The sweet little film follows the pair through their ups and down and also includes several songs (one of which won an Oscar). So whether you're entering your Joanne era or just need more Maggie, this is worth the watch.
Watch it on Prime Video.
21.The Curious Case of Benjamin Button (2008)
Over Christmas break in 2008, me being a pretentious high schooler desperate to prove myself an intellectual, opted to see this film (alone) instead of Marley & Me (which my entire extended family was seeing together). Clearly, I was going through something, but also I became instantly smitten with David Fincher's retelling of the F. Scott Fitzgerald short story. Screenwriter Eric Roth works wonders turning something that is basically a thought experiment asking, "What would it be like to age backward?" into this lyrical epic. This lifelong romance between Brad Pitt's and Cate Blanchett's characters is one for the ages. And if you are anything like 15-year-old me, be prepared to feel very emo and weep off and on throughout.
Watch it on Prime Video.
22.Dead Poets Society (1989)
Curses on Saturday Night Live for making this sketch the first thing I think about when I hear "dead poets society," but if I can push past this, I do remember how wonderfully marvelous the Robin Williams boarding school drama is. The Best Picture nominee (and Best Screenplay winner) follows Williams as he tries to inspire his students by teaching them to love poetry. The film single-handedly taught a generation the meaning of "carpe diem" and two lines of a poem by Walt Whitman. The magic of a great teacher when you're in those prime high school years can do endless good for a person, and Williams here gives you all the inspiration you had (or wish you did) as a teen.
Watch it on Prime Video.
23.District 9 (2009)
District 9 is such an odd little blip in cinema history, but I really do love it. Back in the early 2000s, Peter Jackson was attempting to make a movie based on the Halo video games (which has only just now escaped development hell to air as a TV show) with Neill Blomkamp, an unknown director. Unable to secure the funding, the pair decided to use many of the props they'd already created to make a found footage alien film as an allegory for South African apartheid. Despite an unknown cast and director, the film became a financial success, gaining more and more support until it broke into that year's newly expanded Best Picture race. And while it has faded a bit from memory, especially when compared to its 2009 Oscar competitors like Up, Avatar, and Inglorious Bastards, it is well worth the watch. Please don't hold the fact that Blomkamp went on to make Chappie and introduced Yolandi Visser's terrifying bangs to the world against this film.
Watch it on Prime Video.
24.The Electrical Life of Louis Wain (2021)
Somehow I assumed this movie was about an inventor. Probably because of "electrical" in the title. It is not. It is basically a movie about a man who REALLY, REALLY, REALLY likes cats. Based on the real life of Louis Wain, the film follows Wain (Benedict Cumberbatch), an eccentric artist at the turn of the century who specialized in drawing brightly colored cats. If the film is to be believed, Wain almost single-handedly turned cats into the rival of dogs for most popular house pet. Prior to him, they were considered mangy strays. But after he adopted cats with his wife (Claire Foy) and then spent his entire life drawing them, they took the world by storm, with everyone nabbing a cat after falling in love with his illustrations. If you're a dog person, you now know to whom you should send your hate mail.
Watch it on Prime Video.
25.*Emergency (2022)
If someone pitched me a movie by saying "It's like Booksmart meets The Hate U Give", I would immediately say, "No thanks. That sounds awful." And yet that is exactly how I'd pitch Emergency, which is shaping up to be one of the best films of the year. With strong buzz coming out of Sundance and SXSW, the film follows a trio of POC college seniors whose typical "get to the party" comedy shenanigans are cut short when they find a white girl passed out in their living room. Equal parts horrifying and hilarious, it never pulls punches for the sake of the audience, but still somehow manages to be an incredibly watchable romp. Exceptional performances from RJ Cyler (Me, Earl, and the Dying Girl), Donald Elise Watkins, and Sebastian Chacon make this films tightrope walk between genres possible, and the screenplay by KD Davila deserves a round of shots (or an Oscar nomination depending on what kind of party we're at). Never have I been so worried about bacterial cultures. Never has there been such a scathing use of notes app apology. And never has my body whiplashed back and forth between a belly laugh and sheer horror so quickly. Clearing a spot on my 2022 Best Of Film list as we speak.
Watch it on Prime Video starting May 27.
26.Emma. (2020)
Emma Woodhouse is certainly no stranger to the screen. She was, of course, played by Gwyneth Paltrow in the 1996 film version. Kate Beckinsale played her in a rival 1996 TV version. Emma has been the center of at least eight television adaptations of the Jane Austen novel, several stage adaptations, a manga, and was famously renamed Cher Horowitz in Clueless, which was based on the novel. It didn't appear that we needed a new Emma in 2020, but boy oh boy am I glad we got one, because this quirky, highly stylized period drama from Autumn de Wilde is shocking, biting, and delightful. Anya Taylor-Joy steals the show (as she tends to do) as the it girl of regency England, while a cast of British up-and-comers — including Mia Goth, Josh O'Connor, Connor Swindells, and Callum Turner — take the supporting roles. This is how you properly do a remake.
Watch it on Prime Video.
27.Encounter (2021)
Not a movie to watch if you are easily creeped out by bugs, parasites, or tiny microbial creatures burrowing into your body while you sleep, only to slowly take over your mind and turn you into a zombie. In this sci-fi/horror feature, Riz Ahmed's Malik believes the world to be under threat by microscopic alien lifeforms, and so he kidnaps his children to protect them from their infected mother. As a cross-country chase ensues, with the police and potentially dangerous diseased carriers closing in, Malik struggles to keep his tiny family together. And then, of course, there is the question: Is this all just in his head?
Watch it on Prime Video.
28.Everybody's Talking About Jamie (2021)
If you're a musical and you can get me listening to your song on repeat for a week, then you've got my support. And my Spotify certainly knows I've been jamming to "And You Don't Even Know It" nonstop. The film, based on the smash-hit, Olivier Award–nominated West End musical, follows a teenage boy named Jamie (newcomer Max Harwood) who dreams of becoming a drag queen. The songs are certified bops, and the glitzy choreography is a joy to watch. The supporting cast — including the never bad Richard E. Grant as his drag mentor, Sarah Lancashire as the supportive mother every queer kid wishes they had, and Lauren Patel as Jamie's peppy best friend — also bolsters the film. Inject this kind of pure, wholesome, LGBTQ fun straight into my arm, please.
Watch it on Prime Video.
29.Fargo (1996)
One of my absolute favorite films of all time (especially as a Michigan-accent haver), Fargo follows a snowy kidnapping/ransom attempt that goes wrong when the kidnappers must murder several motorists to keep their secret. That’s when your favorite pregnant Midwestern sheriff, Marge Gunderson (Frances McDormand in an Oscar-winning performance), shows up to solve the crime. The film was nominated for seven Academy Awards and spun off one of the best television series to date (especially Kirsten Dunst’s Season 2). So ah jeez, why dontcha go ahead en watch it?
Watch it on Prime Video.
30.*A Few Good Men (1992)
The legacy of this Tom Cruise military legal thriller is largely the quote "You can't handle the truth!" bellowed by Jack Nicholson in the film's final courtroom scene. While that moment is obviously exceptional, I'd say that the movie as a whole is also very watchable. We don't get many courtroom dramas these days, but the mid-career Tom Cruise vehicles like this and The Firm are fun mysteries to puzzle over with relatively low stakes. Cruise is charming and has solid chemistry with Demi Moore. Nicholson is chewing up the scenery as a gruff Colonel. If you're sitting around with family and looking for something everyone will enjoy, this is a great pick. Especially with the new Top Gun and more Mission:Impossible films in the pipeline, why not revisit young Tom?
Watch it on Prime Video.
31.*Field of Dreams (1989)
While "if you build it, he will come" is the most quoted line from this fantasy baseball saga, the line I quoted most as a child (to my parents' mortification) was James Earl Jones's "peace love dope". There isn't another sports movie quite as whimsical as this one. Kevin Costner plays Ray, an Iowa corn farmer, who starts receiving mysterious messages and dreams instructing him through a series of baseball-related tasks, starting with building a diamond in one of his fields. Jones is tremendous as always as a reclusive writer who Ray crosses paths with, and Amy Madigan is a blast as Ray's blustery wife. (Her PTA meeting scene is especially fun). Oh and the great Gaby Hoffmann is here in child actor form, helping her father to achieve whatever it is the voice is instructing him to do.
Watch it on Prime Video.
32.The Fighter (2010)
Consider The Fighter. Consider one of Christian Bale's extreme body transformations that ended up landing him an Oscar. Consider Amy Adams in one of her six Oscar-nominated roles playing the wife of a boxer. Consider Mark Wahlberg, who played the lead boxer in the Best Picture contender, channeling his own life as a working class Massachusetts boy. Consider David O. Russell's rise as an Academy Award–level director, launching his first in a trio of Best Director noms. And, of course, we must always consider Melissa Leo. Because she gave a harrowing performance as the mother of Bale and Wahlberg's brothers, because she would go on to win the Oscar, and most importantly, because she told us to.
Watch it on Prime Video.
33.Forrest Gump (1994)
Prime Video (like life) is like a box of chocolates. You never know what you're going to get as the service regularly adds and deletes new films from its lineup. Currently on the roster, however, is this Oscar juggernaut, which took home six trophies, including Best Picture, Best Director, Best Actor, and Best Adapted Screenplay. The film follows the titular Gump throughout his life as he bumbles his way through countless misadventures, including cross-country runs, shrimp boat work, the Vietnam War, and, of course, accidentally setting off the Watergate scandal. Perhaps one of the most iconic pieces of American cinema ("JENNY!"), and well worth a rewatch.
Watch it on Prime Video.
34.*Gone Girl (2014)
If you're getting tired of all the girls/women on a train, in a window, or with dragon tattoos who keep showing up in literary thriller adaptations, you really have this film to thank. The David Fincher mystery based on the bestselling Gillian Flynn novel busted the thriller genre wide open, making way for plenty of unreliable narrators, shifty sociopaths, and missing women to follow. The screenplay by Flynn, the directing from Fincher, and the haunting performance by Rosamund Pike at its center are what sets this film apart, however. Pike snagged the film's lone Oscar nomination (it deserved way more), and a strong box office draw and impressive critical feedback made it an instant classic. Amy Dunne. Legend.
Watch it on Prime Video.
35.Good Morning, Vietnam (1987)
GAH! I love Robin Williams so much! He is easily one of my favorite actors and his range is uncanny. The way he can slide from comedy to drama in a single movie (and even in a single scene) keeps you glued to the screen whenever he appears. Nowhere is that more apparent than in his first Oscar-nominated turn in this dramedy about the Vietnam War. Williams plays an irreverent DJ for the military's radio station, straying from his approved talking points, often in ways both humorous and anti-authoritarian. There are definitely some tweaks that a version of this film in 2022 would have regarding its treatment of race and the war itself, but it largely holds up, and for the sake of all the Robin Williams improv DJing, it is worth the watch.
Watch it on Prime Video.
36.Heathers (1988)
Perhaps you know Heathers because you love this '80s film. Perhaps you know Heathers because you love the musical of the 2010s. Or perhaps you know Heathers because you (like me) watched the Heathers: The Musical episode of Riverdale and then backtracked to the source material. Whatever journey you take in order to arrive at Heathers is valid. The dark tale about a rich girl and her new boyfriend trying to murder a clique of Heathers is as terrifying as it is funny. Complete with croquet mallets and '80s blazers, the film is a haunting romp whether you're watching Winona Ryder or Cheryl Blossom.
Watch it on Prime Video.
37.A Hero (2021)
Iranian director Asghar Farhadi has won the Oscar for Best International Feature twice in the last 10 years: once for A Separation in 2011 and then again for The Salesman in 2016. Well, now he's back trying for a third with this year's short-listed title about a man who thinks his ticket out of debtors prison is a purse full of cash that his girlfriend finds. But a fairly simple act goes awry very quickly and threatens to leave him worse off than he started. The intricately subtle set of moral quandaries at this film's center are as terrifying as they seem insignificant, and watching Amir Jadidi act his way through them is mesmerizing. If Farhadi takes home a third Oscar, it will certainly be well deserved.
Watch it on Prime Video.
38.Hotel Transylvania: Transformania (2021)
Your favorite family of monsters is back on the big screen. Well, scratch the "big," since the film was snatched away from a theatrical release because of the Delta variant of the coronavirus and sent to Prime Video for its debut instead, but they are back nonetheless. And in the fourth installment of the much-loved Adam Sandler–led animated franchise, a de-monstering gun goes awry, leading the entire monster cast to be transformed into regular humans (and a plate of jello, in one case). The goofy caper is just as delightful as its previous installments, and the premise sets up a never-ending string of entertaining jokes and bits. It also makes you wonder what monster you'd be turned into if the gun on its opposite setting were aimed at you. Where's my BuzzFeed quiz?
Watch it on Prime Video.
39.*The Hunt (2020)
This film's original release was scrapped because of a frenzied outcry from conservative media in the wake of dual shootings on Aug. 3, 2019. The satirical horror film was eventually reintroduced to the lineup after more careful consideration for a squeeze-it-in-before-the-theaters-shut-down premiere. The plot focuses on a bunch of “deplorables” (i.e., conservatives) being hunted for sport by a posse of liberal elites. Betty Gilpin (Glow) takes center stage as a wily Army veteran, but the cast is stuffed with your favorite comedic actors as Ike Barinholtz (Blockers), Emma Roberts (Scream Queens), and Glenn Howerton (It’s Always Sunny in Philadelphia) all pop up.
Watch it on Prime Video.
40.I Want You Back (2022)
While much hand-wringing has taken place over the death of the rom-com, a genre that peaked in the '90s and largely disappeared after, I'm here to report that a new great has emerged. This new Amazon Original begins with both Charlie Day and Jenny Slate being broken up with, only to meet each other when they're both weeping in the stairwell of their office building. But then the pair comes up with an ingenious plan: ruin the romance of the other's ex in order to drive them back into the arms of their former love. Naturally, this plan goes incredibly poorly, and Charlie and Jenny end up falling in love with each other along the way. A genuine joy to watch, with loads of laughs, great chemistry, and very few cringey moments (sorry to Marry Me), this film is perfect for anyone missing an old-fashioned rom-com, but with texting and dating apps rather than love letters over email.
Watch it on Prime Video.
41.*In Bruges (2008)
Colin Farrell’s character Ray may want nothing to do with Bruges, Belgium, but this film had the opposite effect on me. I have a very intense desire to visit the little town full of cafés and canals, so if you want to be my travel buddy, let me know. Martin McDonagh’s crime comedy follows Ray and Brendan Gleeson’s Ken, both hitmen, as they hide out in Bruges until their recent kills blow over. The sleepy exile turns chaotic, however, when Ken is instructed to murder Ray. Ralph Fiennes plays their profanity-prone boss, and the Academy must have liked the curse words because the screenplay was nominated for an Oscar. I will say that this film has left me terrified of bell towers though, so that’s a potentially negative side effect.
Watch it on Prime Video.
42.*Independence Day (1996)
Moonfall and its "what if the moon was actually an evil alien spaceship" question never quite stuck the (moon) landing, but that doesn't mean Roland Emmerich still isn't the master of the disaster flick. The director (and one of the top openly LGBTQ+ members of his field) was also behind Godzilla, The Day After Tomorrow, and of course, Independence Day, in which humans attempt to fight off an alien attack. The ensemble film gives us memorable performances from Jeff Goldblum, Bill Pullman, Harvey Fierstein, and Will Smith, and it's one of the best Fourth of July themed films. It's this and that scene from The Sandlot. (Unless you want to get real depressed and watch Born on the Fourth of July).
Watch it on Prime Video.
43.Inside Llewyn Davis (2013)
I would like to begin this section with a direct appeal to Spotify: Dear Spotify executives, please put the entire Inside Llewyn Davis soundtrack on your site. Why do we get only three songs? I know it’s probably got something to do with legal things, but it’s rude nonetheless. Thank you. If, however, you would like to hear the entire soundtrack from this Coen Brothers folk musical, you can watch it on Amazon Prime. Oscar Isaac plays the titular struggling folk singer as he tries to make sense of his life, and sings haunting melodies in the process. My beloved Carey Mulligan and the scandal-shrouded Justin Timberlake also make appearances (although their song isn’t on Spotify). This underappreciated, lyrical film should have been showered with more awards and praise than it was. Sometimes the people just get it wrong.
Watch it on Prime Video.
44.The Invisible Man (2020)
It may have had an abbreviated theatrical run due to the pandemic, but this taut sci-fi thriller is living its best life scaring people in the comfort of their own home on streaming. In this film from Leigh Whannell (Saw), Elisabeth Moss’s husband died by suicide…or did he? Perhaps he only faked his death so he could torment her dressed up in a high-tech bodysuit that renders him invisible. The floating knives and mysterious footprints start as unsettling but ramp up to a full-on nightmare by the film’s riveting climax. And while it's a great horror film, it is also a startling representation of the gaslighting women endure even in the #MeToo era.
Watch it on Prime Video.
45.The Joy Luck Club (1993)
The film about four older Chinese immigrant mothers living in San Francisco and their relationships with their Chinese-American daughters is based on the classic, bestselling novel by Amy Tan. The film, only the second studio film in Hollywood's history to include a majority Asian cast, easily recouped its budget, was lauded by critics, and received awards' attention. And yet, in a case of classic Hollywood racism, it wasn't until Crazy Rich Asians came out in 2018 that the third predominantly Asian film was released. In addition to being a beautiful, lyrical tearjerker with plenty of exceptional performances, The Joy Luck Club is also a piece of history. (Also, if you haven't read the book you really should).
Watch it on Prime Video.
46.Knives Out (2019)
You’ve got to love a classic whodunit, especially with an ensemble cast of the caliber of this one. Rian Johnson’s mystery (so well written, its screenplay landed an Oscar nom) focuses on the death of Harlan Thrombey, a famous novelist, and the family desperate to scoop up his inheritance. I know that listing actors is boring, but just go with me here. We’ve got James Bond himself, Daniel Craig, and his future Bond girl/Ben Affleck’s former coffee-walks partner, Ana de Armas. America’s Ass, Chris Evans, is there in a beautiful cable-knit sweater. Halloween badass/yogurt guru, Jamie Lee Curtis, is a suspect, as is two-time Oscar nominee, Michael Shannon. Lime enthusiast, Dakota Johnson’s dad, Don, is here, and so is perhaps the world's greatest living actor, Toni Collette. LaKeith Stanfield is here without his straw hat from Get Out, and so is 13 Reasons Why’s ghostly, Katherine Langford. And just as a final flex, the casting director secured Pennywise’s favorite victim, Jaeden Martell, and the legendary Christopher Plummer, may he rest in peace. Like, really. It’s an all-star lineup, and there's something similar planned for the sequel.
Watch it on Prime Video.
47.*A League of Their Own (1992)
You may or may not be aware that there is A League of Their Own television show coming to Prime Video sometime this year that stars Abbi Jacobson and Nick Offerman. And what better way to prep for that than by watching the original film about a women's baseball league forming while the men are away fighting World War II. Directed by the late, great Penny Marshall, the original has Geena Davis, Madonna, Rosie O'Donnell and others on a team managed by Tom Hanks. The delightful comedy was rare for being a female-led sports film at the time (an issue that isn't much better now) and inspired a generation of sporty girls. This also gave us the classic Tom Hanks line: "There's no crying in baseball."
Watch it on Prime Video.
48.Lincoln (2012)
With Presidents Day movie lists dropping left and right, there has never been a better time to revisit Lincoln. The timing is made even better by the fact that its director, Steven Spielberg, is in the middle of an Oscar campaign for his remake of West Side Story. And perhaps even better because the stovepipe hat and Honest Abe beard were all the rage at 2022 NYFW (okay, that's actually a lie). Anyone who has taken five seconds of a US history class (or just watched a Rozerem commercial) knows the basic facts on Mr. Lincoln. Here he's played by Daniel Day-Lewis (who legit pretended to be Abe for months) in an Oscar-winning performance. The film got 12 Oscar noms. It probably should have won Best Picture. I'm still not exactly sure what "four score" is, but otherwise, you'd be hard pressed to find a better presidential film (unless, of course, you count Dave).
Watch it on Prime Video.
49.The Lighthouse (2019)
Robert Eggers’ follow-up to The Witch (where we all learned to live deliciously) is a claustrophobic psychological nightmare and anything but delicious (unless dead seagulls and farting whet your appetite). Shot in black and white with a nearly square aspect ratio, the film resembles an 1800s home video as it tracks Willem Dafoe and Robert Pattinson’s characters to a rocky island lighthouse. Fueled by alcohol and cut off from society, the pair descend into a salty, windswept madness. This is certainly not for everyone, but those of you with a strong constitution and love of psychological horror will find this a riveting exploration of the untethered mind. Watch it while we anxiously await The Northman, Eggers’ next film.
Watch it on Prime Video.
50.Love & Friendship (2016)
You have probably seen Pride & Prejudice, Sense & Sensibility, or Emma, but I'm here to tell you about the recent adaptation of Jane Austen's lesser-known novel Lady Susan, which was published long after her death. Kate Beckinsale plays the titular, recently widowed protagonist, who, in true Austen fashion, is on the prowl for a wealthy husband, not just for herself but for her daughter. No one does Regency wit and matchmaking quite like Jane Austen, and the film is a thrilling romantic dramedy. Also, assuming you weren't assigned this book in college, the tale should be fresh, whereas we've all seen Mr. Darcy propose to Elizabeth Bennet 100 times.
Watch it on Prime Video.
51.*Love & Monsters (2020)
As a completist, I make it a point every year to watch every Oscar-nominated film (shorts, documentaries, and song nominees included). Often this is a thankless task, but occasionally you stumble upon greatness! I'd never heard of this dystopian romance before it nabbed a Best Visual Effects nomination during the 2020 COVID Oscars. It had gone straight to VOD and boasted little star power beyond Teen Wolf actor Dylan O'Brien. This was the best surprise of the season. Witty, fresh, and full of imaginatively designed monsters, this film is a romp. O'Brien's Joel must travel through monster-infested territory to reach his true love and the whole thing is hilarious and incredibly smart. I recommend this film so often, and it was honestly better than at least half of the Best Picture nominees that year.
Watch it on Prime Video.
52.*Mamma Mia! (2008)
It's a star-studded cast singing ABBA music in Greece for two hours. Do I really need to sell you on this film any more? Its based on a Tony-nominated stage musical. It has Meryl Streep wearing overalls. It has a brilliant sequel where Cher shows up and sings "Fernando." Tony Garcia is named "Fernando" precisely for this bit. Horny Christine Baranski sings to young men crawling around on a beach. (Why has the woman never been nominated for an Oscar? Why was she not nominated for this?) Amanda Seyfried became a household name. Pierce Brosnan bulldozed his way through a few songs. Everyone booked trips to Santorini. One of the most iconic movie musicals ever made, and I would argue one of the best stage-to-film adaptations. My grandparents saw it a dozen times in theaters they loved it so much, and shame on everyone who saw it less.
Watch it on Prime Video.
53.Manchester by the Sea (2016)
Manchester by the Sea is a beautiful, if disastrously depressing film written and directed by Kenneth Lonergan. Michelle Williams and Casey Affleck both give incredible performances (even if Casey’s more recent controversies have detracted from his star power). But what I’d like to discuss is the birth of Lucas Hedges into the American consciousness. Hedges plays Patrick, a 16-year-old with a THICK Boston accent, who goes to live with his depressed uncle (Affleck) after the death of his father. His performance is so strong that it nabbed him a rare young male Oscar nomination and launched him into lead roles in subsequent films like Ben Is Back and Boy Erased. He would also go on to become an A24 darling in films like Lady Bird and Waves. Just as I couldn’t stop looking at this recent photo of him, I was transfixed by his presence here and have loved watching his journey to stardom.
Watch it on Prime Video.
54.Master (2022)
2022 Sundance was ruled by Regina Hall, who after decades of strong work in films like Scary Movie and The Best Man finally seems to be breaking through into prestigious lead roles like that in Support the Girls, Black Monday, Honk for Jesus. Save Your Soul., and Master. In this horror film, Hall plays the first Black master at a largely white New England private college. The campus is supposedly haunted by the ghost of the first Black student ever admitted, BUT, hear me out, perhaps it is mostly haunted by a lot of racists. Hall, of course, is the consummate professional and plays her role as the conflicted, haunted, horrified academic perfectly. Terrifying and speaking to the broader cultural toxin that is WASP-y, elitist colleges, the film has the potential to break through into awards conversations as well.
Watch it on Prime Video.
55.Mayor Pete (2021)
I think it's easy in 2021 (post–run for president, post–arrival in Washington, DC, as secretary of transportation, and post–shirtless thirst trap) to forget what a trailblazer Pete Buttigieg is. Putting aside how you feel about his politics, his track record, or his stoic demeanor, his fairly successful campaign as an openly gay man was an incredible achievement for LGBTQ rights. This documentary, while rehashing many of the campaign facts that you already know, does a nice job of reminding viewers how powerful it was for many people (especially not those in liberal urban enclaves) to see a married gay man running for president. The film also provides some interesting behind-the-scenes moments, including him repeatedly having to face a likability/relatability question and his eventual decision to drop out. You may not like Mayor Pete, but you can't help but acknowledge what he was able to accomplish.
Watch it on Prime Video.
56.Murder on the Orient Express (1974)
Whether you have enough champagne to fill the Nile, a train, or a water bottle you're smuggling into the movie theater, a boozy Agatha Christie viewing is always a treat. Rather than slogging through the newest Kenneth Branagh adaptation, however, might I suggest giving the 1974 version of Murder on the Orient Express or its 1978 sequel, Death on the Nile, a try? Both films are jam-packed with film legends who slink around their confined transportation device, discovering dead bodies, telling lies, and giving suspicious glances from the shadows. Among this cast are Ingrid Bergman, Vanessa Redgrave, Albert Finney, and Sean Connery. If you like a whodunit, then this is sure to deliver more than watching Gal Gadot and Armie Hammer quote Shakespeare while having sex on an Egyptian ruin ever will.
Watch it on Prime Video.
57.My Name Is Pauli Murray (2021)
I am ashamed to say that prior to watching this documentary, I had no idea who Pauli Murray was. If you, too, have never heard of this fascinating, groundbreaking, trailblazing individual, then you need to hustle right on over to Amazon and give this a watch. A civil rights activist who refused to give up her seat on the bus before Rosa Parks. An African American lawyer whose work paved the way for Ruth Bader Ginsburg's landmark cases on sexism. A queer intellectual who sought to understand gender and sexuality during a time before modern labels. Murray is an icon we should be learning about in school, so if you're a schoolteacher and you're reading this article, wheel that TV into the classroom and press play.
Watch it on Prime Video.
58.Napoleon Dynamite (2004)
"Tina, you fat lard, come watch this movie." Is there a movie more quotable than the 2004 sleeper hit? "Napoleon, give me some of your tots." "Your mom goes to college." "Make yourself a dang quesadilla." "I caught you a delicious bass." And of course my favorite: "How much do you want to bet I can throw this football over them mountains?" The film made by friends for approximately $12 — with its biggest star being Hilary Duff's sister — crawled its way into the minds of viewers to the point where everyone I knew had seen it dozens of times and could quote it word for word. The "Vote for Pedro" shirt. The "Canned Heat" dance. Tetherball. Dare I say that this is potentially the most iconic film of the new millennium? I mean, I don't have any scientific numbers here, but I would have to imagine there was a precipitous decline in 1% milk sales post-release. This film MADE A MARK.
Watch it on Prime Video.
59.Never Rarely Sometimes Always (2020)
Never Rarely Sometimes Always is not an easy watch, nor is it necessarily a fun one, but it is necessary, especially to those of us lucky enough to have avoided making the choice as to whether or not to have an abortion. Eliza Hittman's award-winning indie follows Autumn (Sidney Flanigan), a pregnant 17-year-old who must travel from Pennsylvania to New York in order to get an abortion without her parents' consent. The journey is fraught on so many levels as she comes up against bureaucratic roadblocks at every turn, and with little money or support, must face those crises largely alone. Autumn's relationship with her best friend Skylar is the bright spot of the film as the girls work together on their trip to New York's Planned Parenthood, and the intake where Autumn is repeatedly asked questions with the titular answers is a heart-wrenching piece of cinema. This is also the most effective use of the Port Authority Bus Terminal in film history. You feel every miserable minute that they have to spend there.
Watch it on Prime Video.
60.*Now You See Me (2013)
Not since Harry Houdini have magicians been so cool. When a group of hotshot Las Vegas magicians dubbed the Four Horsemen somehow manage to steal millions of dollars from a French bank account, the FBI gets involved. Their agent (played by Mark Ruffalo, who always looks good as a concerned man wearing glasses) attempts to shakedown the supergroup made up of Isla Fisher, Jesse Eisenberg, Woody Harrelson, and Dave Franco. The film is twisty and involves plenty of tricks, chases, and elaborate "this is how we actually did it" montages. Unlike its dreadful sequel, this is a fizzy, entertaining romp, and well worth throwing on during a flight, an evening in, or the 10 minutes you spend chained to the bottom of a vat of water before miraculously appearing on a balcony.
Watch it on Prime Video.
61.O Brother, Where Art Thou? (2000)
I only recently saw this Coen Brothers film for the first time, but boy oh boy has the soundtrack been living in my head rent free for YEARS AND YEARS. I don't know about you, but this set of old folk songs and gospel spirituals had a CHOKEHOLD on my church growing up. The number of times I've sung "Down to the River to Pray" with a room full of old white people? Hundreds! But mildly traumatic memories aside, the soundtrack is a banger and the (perhaps less famous) film about a trio of escaped prisoners in the Depression Era south is a fun watch. It's loosely based on The Odyssey for my English majors out there, and includes great performances from George Clooney, John Candy, and of course John Turturro, who you may know from his most recent villainous turn in The Batman. So oh sister, let's go down, let's go down, come on down to the TV to watch.
Watch it on Prime Video.
62.*Office Space (1999)
Office Space was ahead of its time. The indie film, which grew into a beloved cult classic, somehow knew how to become a meme well before the internet even knew what a meme was. The office is the definition of a corporate wasteland, and Ron Livingston's Peter Gibbons navigates the TOO REAL everyday realities of a horrible boss, a meaningless job, and technology malfunctions. The supporting cast including Jennifer Aniston and Barry's Stephen Root (who just wants his red stapler) are strong and oh so quotable. And then of course there is the iconic, oft-imitated scene of the office workers destroying a printer. Who among us hasn't wanted to take a bat to some outdated piece of equipment your employer insists you use daily? I know I'm lined up and ready to smash.
Watch it on Prime Video.
63.One Night in Miami (2020)
In 1964, famed civil rights activist Malcolm X, boxer Muhammad Ali, football star Jim Brown, and singer Sam Cooke all spent an evening together in a hotel room in Miami. That historic meeting serves as the basis for this film, directed by Regina King (an Oscar-winning actor herself) and adapted by Kemp Powers, who also wrote the play and Pixar's Soul (big year for him!). Focused on the relationships between these four great men, the film creates fictional dialogue that aims to unpack race, privilege, and the responsibility that comes with fame. Hamilton’s Leslie Odom Jr. plays Cooke (a performance for which he was Oscar-nominated), but it's Kingsley Ben-Adir’s take on Malcolm X that is most captivating. Never has such a long stay in a hotel room been so interesting.
Watch it on Prime Video.
64.*Platoon (1986)
If you (like me) are currently a bit smitten with Willem Dafoe, then you've got to watch Platoon. Before he was delivering one of 2021's best performances as the Green Goblin in Spider-Man: No Way Home, being a great hotel manager in The Florida Project, or farting up a storm in The Lighthouse, he was playing a conflicted soldier in the 1986 Best Picture winner. Part of Oliver Stone's Vietnam War trilogy based on his time in the war, this drama follows three young men (played by Dafoe, Charlie Sheen, and Tom Berenger) as they wage war in Southeast Asia, struggling with the morality of their actions. More philosophical than your typical war movie, it is a war movie for people who don't typically like the genre. And as one of Dafoe's four Oscar nominations, it's a must-watch if you're a card-carrying member of his fan club.
Watch it on Prime Video.
65.Pride (2014)
I LOVE to promote a good LGBTQ film, and this funny little historical British dramedy is a fantastic one. Back in 1984, during a British miners' strike, gay activist Mark Ashton (Ben Schnetzer) realized that the police were too busy focusing on the miners to focus on their usual harassment of the gay community, and so he started Lesbians and Gays Support the Miners to help a fellow group of oppressed folks. It’s this fight by the LGBTQ community on behalf of the labor class that serves as the plot here. Hot priest Andrew Scott is here, along with 1917’s George MacKay and Professor Umbridge, aka Imelda Staunton. The film is charming and uplifting and shows you how underdogs helping underdogs can do a lot of good for everyone.
Watch it on Prime Video.
66.The Proposal (2009)
One could argue (and I will) that The Proposal is our most recent great rom-com. The genre, which thrived in the '80s and '90s, has been largely overlooked as of late, and no one has successfully topped the Ryan Reynolds–Sandra Bullock vehicle. In it, the heartless, all-business head of a publishing company (Bullock) demands that her kindly assistant (Reynolds) marry her in order to avoid her deportation back to Canada. As part of the ruse, however, she must return home to his native Alaska to spend time with his family. And as the laws of the rom-com dictate, the once-enemies fall in love along the way. It should also be noted that this is the film responsible for the Betty White renaissance of the early 2010s. How could you not love a sassy ole granny?
Watch it on Prime Video.
67.*A Quiet Place Part II (2020)
Please read this blurb in a whisper, because if you don't then a giant tentacled beast will come eat you, your deaf daughter, your brand new baby, and your dumbass son. (Sorry Noah Jupe. I love you, but your character here is itching to get everyone killed). The sequel to the much-loved 2018 film directed by and starring John Krasinski is now only directed by John Krasinski, (Not gonna say why, but I'll give you three guesses), but Jupe, Emily Blunt, and Millicent Simmonds are back hustling silently through the weeds. The sequel expands the world beyond the confines of the family farm and provides some backstory as well. It's an entertaining horror/action movie and Emily Blunt is acting her ass off (without speaking) yet again. Someone nominate her for an Oscar.
Watch it on Prime Video.
68.Raging Bull (1980)
At this point we've all seen plenty of boxing movies. Rocky, Creed, The Fighter, Million Dollar Baby. But when it comes to artistry, none quite matches Martin Scorsese's boxing epic. The early Scorsese film earned eight Oscar nominations including his first for Best Director, a win for his longtime editor, Thelma Schoonmaker, Robert DeNiro's second Oscar win (and somehow his most recent), and Joe Pesci's first nomination. The black-and-white film follows DeNiro's Jake LaMotta, a self-destructive boxer as he bulldozes through his life, leaving a trail of carnage in his wake. It also must be said that DeNiro is BUILT in this film. He put on 60 pounds of muscle for the role, and I would be terrified to meet him in the ring. (Full disclosure, I'd be terrified to meet almost anyone in a boxing ring, but 1980 DeNiro especially).
Watch it on Prime Video.
69.Revolutionary Road (2008)
Here is my chance to plug my ranking of Leonardo DiCaprio's film performances. I am a massive fan of Leo (the internet is telling me the technical term is a DiCaprihoe), and his performance here is exceptional. In his lineup of buzzy, big-budget films, this small period drama certainly isn't his most well-known work. If it wasn't for the historic reunion of the Titanic stars, here in another doomed romance, the film likely wouldn't have registered at all. I love this quiet little film though and DiCaprio's performance in it. What happens when you're in your 30s, seemingly have everything you've ever dreamed of, and are still profoundly unhappy? That's what Kate and Leo grapple with here as their marriage and life disintegrates through repeated acts of depressed self-sabotage. Michael Shannon gives an Oscar-nominated performance as the other man, and Kathy Bates is great as a blithering realtor. This makes me excited to watch Sam Mendes' upcoming project with Olivia Colman and Colin Firth that appears to be in this vein.
Watch it on Prime Video.
70.Rushmore (1998)
Before Wes Anderson's style and filmmaking became legendary, he made a little film called Rushmore about a high school student (Jason Schwartzman) and a rich middle-aged man (Bill Murray) who become friends, until they realize they are both in love with the same teacher at his school. Watching the quirky picture, you can see the budding of Anderson's signature style, but it doesn't get in the way of the storytelling, as it does in some of his later works. Murray is fabulous (as always), and Schwartzman keeps up with him the entire time. While the film was not initially successful, it's picked up more and more fans over the years as Anderson's star has risen. Its soundtrack, full of British Invasion tracks, is another reason to watch, if you needed one.
Watch it on Prime Video.
71.Saved! (2004)
Hilary Faye Stockard is FILLED with Christ's love and will keep you from backsliding into the flames of hell. Mandy Moore's devoutly Christian high schooler is one of the most entertaining characters I've seen on screen, especially as someone who grew up in the extremely Evangelical world of purity conferences, prayer groups, and not playing Mario Kart because Bowser was considered a demonic figure. This high school comedy follows Mary Cummings (Jena Malone) as she struggles with a crisis of faith and the reactions of her friends. The Princess Diaries' Heather Matarazzo is here with delightfully feathered hair, Macaulay Culkin is here as the non-Christian rebel, and Lord knows I love a plot involving an attempted exorcism in the back of a handicap-accessible van. Thank Father, Son, and Holy Ghost/House of Gucci for this one.
Watch it on Prime Video.
72.Short Term 12 (2013)
I don’t know what was happening on the set of Short Term 12, but someone had a rabbit's foot or made a deal with the Illuminati, because truly, everyone in this tiny indie drama has gone on to have their careers BLOW UP! There’s Captain Marvel herself, Brie Larson. There’s Booksmart’s scene-stealer Kaitlyn Dever. There’s Best Actor/Freddie Mercury impersonator Rami Malek. There’s Brooklyn Nine-Nine star Stephanie Beatriz. And of course, there is the very recent Oscar nominee for Judas and the Black Messiah, LaKeith Stanfield. This film, which focuses on a group home for troubled teenagers, is funny, sad, and heartwarming in its own right, but watching all your current faves’ younger selves is a trip.
Watch it on Prime Video.
73.*Shrek (2001)
It's such a shame they cut Shrek dressed in leather, floating in the sky and dancing to a "Macarena"/"Material Girl" remix from the original film. Truly one of the most pivotal scenes in cinema, and you can only find it on TikTok. BUT moving on to the actual Oscar-winning film, itself, it is in fact perfection on screen. From the opening that uses Smash Mouth's "All Star" to the karaoke dance party at the end, the film is a blast. The clever setup involving an ogre rescuing a fairy tale princess. The voice acting from Cameron Diaz, John Lithgow, Michael Myers, and Eddie Murphy. The "Welcome to Duloc" song. I ride hard for Shrek (and it's perfect sequel). It's like an onion (not a parfait). Every time you watch it, a new layer is pealed back to its masterfulness. I'm gonna stay up late, watching this movie, and in the morning, I'm making waffles.
Watch it on Prime Video.
74.*Sideways (2004)
Some would say (and by “some” I mean “me”) that Paul Giamatti’s best work is in Big Fat Liar. Far more would say he shines in this Best Picture nominee. The dramedy follows Giamatti’s depressed, unsuccessful writer, Miles, and his has-been soap opera star, Jack (Thomas Haden Church in an Oscar-nominated role), as the pair take a trip to wine country before Jack’s wedding. What follows is a chaotic, rambling film that is somehow cheerful, depressing, inspiring, and hilarious all in one swoop. It’s a rumination on aging and friendship that snatched five Oscar nominations and took home the trophy for the screenplay.
Watch it on Prime Video.
75.Signs (2002)
The way crop circles truly took over all my mental energy after this film came out. Growing up with a cornfield for a back yard, I was CONVINCED that aliens were gonna come down and leave me messages of doom via crushed corn stalks. While M. Night Shyamalan's career may have wandered off into the fields and never returned (Old is one of the worst movies I've ever seen), his early work remains largely unimpeachable. This sci-fi horror flick about a family facing an extraterrestrial invasion is engrossing and has fun performances from Joaquin Phoenix, Rory Culkin, Abigail Breslin, and Cherry Jones. Watching it does involve seeing Mel Gibson on screen, but the truly terrifying birthday party scene makes up for that. I'm also fairly certain my roommate was HIGHLY impacted by this film, because why else would she leave half-drunk glasses of water all over our apartment?
Watch it on Prime Video.
76.The Sixth Sense (1999)
If you are one of the 12 people left on Earth who doesn't know the twist ending of The Sixth Sense, then please, for the love of god, go watch this movie. I'm not going to spoil it, but not everyone is as considerate as me regarding 20-year-old spoilers. But I will say that Haley Joel Osment's "I see dead people" means that he can see ghosts. They're chatting him up and passing along messages they'd like relayed to their living loved ones. Of course, he sees the terrifying Mischa Barton ghost, but he also imparts a message from his grandmother to his mom (Toni Collette) in this Oscar nomination-earning scene. I don't know if we have a definitive ranking, but I'm willing to go out on a limb and say that HJO in this film might be the cutest medium ever?
Watch it on Prime Video.
77.Sound of Metal (2019)
One of this year’s freshly minted Best Picture nominees, Sound of Metal follows Ruben, a heavy metal drummer who comes to the (at first) horrifying realization that he is losing his hearing. The indie drama, which continued to pick up more steam and accolades through the awards season, stars Riz Ahmed in the lead as he mourns his hearing and struggles to find ways to cope. Both he and Paul Raci, who plays the deaf leader of a shelter for recovering addicts, landed Oscar noms for their performances, and Olivia Cooke, who plays Ruben’s girlfriend, rightfully should have received one as well. This fascinating film also substantiates my mom’s claim that "you are going to lose your hearing from turning the radio up too loud."
Watch it on Prime Video.
78.Sunset Boulevard (1950)
We start with a mansion on Sunset Boulevard. And oh look, there is a body floating facedown in the swimming pool. Whose body is it? How did it get there? You’ll have to watch to find out. The black-and-white Hollywood classic tracks the events leading up to the mysterious death, as William Holden plays a young screenwriter who is slowly sucked into the web of the reclusive former silent-film star Norma Desmond (Gloria Swanson). The iconic film, which gave us lines like, “Mr. DeMille, I’m ready for my close-up,” was nominated for 11 Oscars and holds an ironclad spot in the film canon. A perfect film, it feels startlingly modern even as a ’50s noir, and it packs just as much punch today as it did at its release.
Watch it on Prime Video.
79.*Taken (2008)
The influence of Taken on our cinematic landscape cannot be overstated. In 2008, when it was released, the whole thing was seen as an anomaly. An action film starring a nearly 60-year-old actor most notable for dramas like Schindler's List? Who would go and see that? Well, apparently, a lot of people (and a lot of dads). The film was so successful, that it launched a whole genre of old-man action films, including a dozen for Liam Neeson himself. Now Sylvester Stallone, Bruce Willis, and Mel Gibson are all talking up their "very particular sets of skills." Despite all of the flawed follow-ups, however, Taken still stands as the exemplar of the genre, and far be it from me to pass up an evening of Neeson taking out 50 baddies, all half his age.
Watch it on Prime Video.
80.Tangerine (2015)
If you haven't watched Sean Baker's revolutionary film about transgender sex workers in Los Angeles, then you need to stop what you're doing and go watch immediately. I'm not exaggerating when I say it was the best film I saw during my never-ending pandemic film binges. Sin-Dee Rella (Kitana Kiki Rodriguez), one of the pair of sex worker besties at the heart of the film, goes on a rampage when she learns her boyfriend is dating a new woman. Finding the "other woman," Dinah, Sin-Dee drags the beleaguered Dinah around the streets of LA for an evening on the hunt for her pimp/BF. A movie about trans people starring trans people, this is a win-win.
Watch it on Prime Video.
81.The Tender Bar (2021)
With Golden Globe and Screen Actors Guild nominations, Ben Affleck is a bona fide awards season hopeful in this coming-of-age drama about a Pulitzer Prize–winning journalist growing up with his eccentric family on Long Island. Affleck plays the literary, yet rough-and-tumble owner of a bar who mentors his nephew (Tye Sheridan) on all things life, love, and booze. The George Clooney–directed period piece also features Lili Rabe and Christopher Lloyd as the supportive mother and crotchety grandfather respectively. Plus, who doesn't want to listen to bickering in Long Island accents?
Watch it on Prime Video.
82.The Terminator (1984)
“I’ll be back.” This Arnold Schwarzenegger sci-fi action film not only has gone on to spawn multiple spinoffs but also gave us some of the most quotable lines in cinema history. The former governor of California plays an evil AI cyborg assassin sent back in time to kill Sarah Connor (Linda Hamilton), the woman who will eventually give birth to the man who will save humankind. While the later films in the franchise are more action focused, the original is basically a horror film with the terminator killing anyone that gets in the way of him murdering Sarah. Watch your favorite Austrian bodybuilder deliver his classic lines before his fake skin is melted off and he turns into a terrifying red-eyed robot.
Watch it on Prime Video.
83.Time (2020)
Rarely do we get a documentary as raw and moving as Time. The film follows Fox Rich, using over 25 years’ worth of home videos as she fights tirelessly for her husband, Rob, who is serving time in prison for his participation in an armed bank robbery, to be granted clemency. What filmmaker Garrett Bradley thought would be a short film turned into a feature when Fox handed her over 100 hours of home video footage taken while her husband was in prison. Bradley then took the home videos and her own footage, converted it all to stunning black and white, and built the moving, 81-minute-long final product. The documentary, which was nominated for an Oscar, vividly shows the flaws of the criminal justice system and how that can deeply affect the families of those struggling through it. It’s a beautiful statement as to what can be accomplished if you try hard enough, and how important it is to have someone tirelessly in your corner.
Watch it on Prime Video.
84.The Tomorrow War (2021)
A recent 2021 release, this Chris Pratt sci-fi film is set in a world in which aliens overrun the planet in 30 years. The future, therefore, is drafting humans from the present to time-travel to the future to fight off the aliens in order to save humanity. Pratt, playing a former Green Beret, is drafted alongside a ragtag crew including Sam Richardson (Veep) and Mary Lynn Rajskub (aka Gail the Snail from It's Always Sunny in Philadelphia). While the time-travel logistics are a bit murky, the action sequences (especially on a giant, oil rig–style military base) are incredible, and the monsters will give you nightmares.
Watch it on Prime Video.
85.Train to Busan (2016)
South Korean puts out great horror films, including this zombies-on-a-train flick. When a zombie apocalypse breaks out, a group of survivors must band together as their high-speed train from Seoul to the titular Busan begins to fill up with overeager flesh eaters. Honestly, given the choice, I’d take snakes on a plane any day of the week.
Watch it on Prime Video.
86.Unbreakable (2000)
I cannot think of this movie without singing this song to myself. I'm waiting for the Samuel L. Jackson cover. M. Night Shyamalan's follow up to The Sixth Sense was this remixed superhero tale about a man with super strength (Bruce Willis) whose kryptonite is water, and a man with brittle bones (Jackson) but a powerful mind. The film appeared to be a standalone until the characters were revisited 14 years later with the release of Split and then Glass to complete a superhero trilogy. Willis and Jackson appear to be having a lot of fun here, and their chemistry makes the campy flick work.
Watch it on Prime Video.
87.Under the Tuscan Sun (2003)
Before we were Eat Pray Loving, we were Under the Tuscan Sunning. If you're in the middle of your life and finding yourself aimless post-divorce, then the obvious solution is to travel to Italy, eat some pasta, and write yourself toward a new life. In this romantic dramedy, Diane Lane's Frances does just that at the prodding of her friend Patti (the never-not-funny, Sandra Oh). While gallivanting through the Italian countryside, Frances searches for a new love, begins writing again, and tries to find direction in life after the one she had imploded. If your life is going well, enjoy the breezy watch. If your life is going poorly, perhaps consider booking a ticket.
Watch it on Prime Video.
88.Weekend at Bernie's (1989)
If you love humor that involves a corpse, then I've got the perfect film for you! In this very dark comedy, Larry and Richard arrive at their boss's house for the weekend only to realize that he has died. The pair decide to pretend the boss (Bernie) is still alive in order to avoid being suspected of killing him only to find out that he's put a hit out on them in order to cover up his own embezzlement. The result is a gut-busting classic '80s comedy full of gags that involve propping up dead bodies. Not since Clue have we seen such great corpse comedy. So prop up whatever bodies you've got laying around on your couch, pop the popcorn, and get ready for a fun movie night with the dead.
Watch it on Prime Video.
89.What the Constitution Means to Me (2020)
I would hazard a guess that most of us know next to nothing about the US Constitution. Perhaps you memorized the preamble in school, but even that I never understood. Heidi Schreck, however, was well versed in the legal document from a young age, traveling around the country to compete in speech competitions about the Constitution for scholarship money. Now an adult, Schreck wrote and starred in a Broadway show about her experience with this document and what it means for our country and culture today. The deeply personal and incredibly charming show was recorded for your non-Broadway viewing (thank goodness this is happening more and more these days) and is available on Amazon. It will teach you a thing or two about this essential American document while also forcing you to ask, "Should I know more about the laws that govern me?"
Watch it on Prime Video.
90.*Zero Dark Thirty (2012)
And last, but certainly not least, we've got recent Oscar-winning Best Actress Jessica Chastain starring in Oscar-winning Best Director Kathryn Bigelow's Best Picture nominee about the hunt for Osama bin Laden. A taut, military thriller, the film follows the team of Americans post-9/11 who were searching for the terrorist kingpin behind the attacks. Chastain is excellent here (when is she not?) and a supporting cast that includes Joel Edgerton, James Gandolfini, Chris Pratt, and plenty of others bolsters the film. I personally didn't know much about this mission when I watched the film, and seeing everything that went into tracking bin Laden down was incredible (and slightly terrifying if you think about it). Should it have won more Oscars than it did? Absolutely.
Watch it on Prime Video.
* Denotes title that has been newly added to Prime Video for May.
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