The best romantic comedies on Max

From screwball to Shakespeare, romantic comedies have range. Love goes through many life stages, and the films on this list will escort you through all of them. Whether you're a silent film star in Old Hollywood, a pregnant teen in the early aughts, or one of the occupants of Murderess Row at the height of the jazz age, these movies will carry you from meet cute to matrimony. And along the way, they'll show you how to live, laugh, and love in ways a sign from TJ Maxx could never.

<i>13 Going on 30</i> (2004)

Jennifer Garner launches a full-scale charm offensive in 13 Going on 30, a fantasy romantic comedy about Jenna Rink, a 13-year-old who wishes to be grown up after a disastrous birthday party. A cross between Big and The Devil Wears Prada, the film follows Jenna from her childhood home to her New York City luxury apartment and dream job at a magazine. As the teen in a 30-year-old's body attempts to understand what has happened to her in the last 17 years, she must confront whether growing up was everything she had hoped for. Garner filmed the movie while on hiatus from her TV show, Alias, and her joyful physicality and unabashed childlike enthusiasm couldn't have been more of a departure from her ass-kicking work as Sydney Bristow. One of the purest and most rewatchable rom coms from the early aughts, 13 Going on 30 represents some of the best the genre has to offer, and is a joy to watch regardless of your age.       

Where to watch 13 Going on 30: Max

EW grade: A- (read the review)

Director: Gary Winick  

Cast: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis

Related content: Jennifer Garner remembers late director Gary Winick

<i>Casablanca</i> (1942)

Despite boasting some of the best quotes in all of cinematic history, Casablanca was just one of many films churned out by the studio system in the early years of World War II. But something about the movie's heart-wrenching love triangle, political and social relevance, and lush setting charmed viewers, propelling the project to an unexpected Best Picture win, and a permanent spot on almost every Best Of list. Electricity rations were common at the time of the movie's release, but entirely unnecessary — the sexual currents pulsating between stars Humphrey Bogart and Ingrid Bergman had to have been strong enough to generate power for a small city, at the very least.

Where to watch Casablanca: Max

EW grade: A (read the review)

Director: Michael Curtiz

Cast: Humphrey Bogart, Ingrid Bergman, Paul Henreid, Claude Rains

Related content: What would J. Lo and Ben's Casablanca look like?

<i>Chicago</i> (2002)

Pop. Six. Squish. Uh-uh. Cicero. Lipschitz: Murder gets a Fosse-style makeover in the film adaptation of the hit Broadway musical, Chicago. At the height of the jazz age, vaudeville star Velma Kelly (Catherine Zeta-Jones) and chorus girl Roxie Hart (Renée Zellweger) are both arrested for separate incidents and charged with murderer. While awaiting their trials in the Cook County Jail, both attempt to use the acclaimed lawyer Billy Flynn (Richard Gere) to manipulate the press into helping them gain fame and sympathy — and avoid the death penalty. This Rob Marshall-directed film garnered six Academy Awards and was the first musical to win the Oscar for Best Picture in 35 years. Upon first viewing, you might be inclined to agree that the production team "had it coming."

Where to watch Chicago: Max

EW grade: A- (read the review)

Director: Rob Marshall 

Cast: Catherine Zeta-Jones, Renée Zellweger, Richard Gere, John C. Reilly, Queen Latifah, Taye Diggs, Dominic West, Christine Baranski

Related content: Chicago director Rob Marshall breaks down the killer instincts behind 'Cell Block Tango'

<i>Election</i> (1999)

Tracy Flick walked so Gilmore Girls' Paris Geller could run. In the 1999 romantic comedy Election, Reese Witherspoon and Matthew Broderick star as an overachieving high school student and a popular history teacher, whose relationship becomes increasingly combative as Tracy (Witherspoon) attempts to run for president of her school's student body. Determined to prevent Tracy from emerging victorious in an unopposed race, Jim McAllister (Broderick) recruits a sidelined football player (Chris Klein) as an opposition candidate, but finds that his commitment to teaching Tracy a lesson comes at the expense of his personal and professional life, as well as his sanity.

Adapted from a novel by Tom Perrotta and directed by Alexander Payne (Sideways), Election was incredibly well-received by critics, earning an Oscar nomination for Best Adapted Screenplay and the top slot on our list of Reese Witherspoon's best movies. The film may have faltered at the box office, but it remains one of the most enduring and funniest high school films of all time.

Where to watch Election: Max

Director: Alexander Payne

Talent: Matthew Broderick, Reese Witherspoon, Chris Klein

Related reading: Reese Witherspoon to reprise Election role in sequel Tracy Flick Can't Win

<i>Garden State</i> (2004)

Zach Braff's Garden State — the story of a struggling young actor's return home to New Jersey after the death of his mother — is not a perfect movie. Written by Braff during a period of depression and inspired by his own feelings of numbness, the film interrogates themes like mental illness, medication, growing up, and falling in love, sometimes nailing the sentiments and other times falling short. In spite of its deficits, however, the romantic comedy was a sleeper hit when it premiered in 2004, a reception attributable to the film's excellent soundtrack, objectively sick cast, and resonance with a young generation staring down the barrel of adulthood. Starring Braff as Andy, the film's protagonist, and Natalie Portman as his eccentric and compulsively dishonest love interest, Sam, the film is often compared to The Graduate, but remains a singular romantic comedy that demands an emotional reaction from its audience.

Where to watch Garden State: Max

EW grade: B (read the review)

Director: Zach Braff

Cast: Zach Braff, Natalie Portman, Peter Sarsgaard, Ian Holm, Jean Smart, Jackie Hoffman, Ann Dowd, Method Man, Jim Parsons

Related content: Zach Braff reflects on writing Garden State's 'manic pixie dream girl': 'I was a very depressed young man'

<i>I Love You, Beth Cooper</i> (2009)

Released two years after Superbad showed the world how the nerd can get the girl, I Love You, Beth Cooper tells a similar story from a different perspective. Another coming of age comedy about a nerdy high schooler trying to rewrite his story before transitioning out of his hometown, Beth Cooper follows Denis Cooverman (Paul Rust), the senior class valedictorian who uses his graduation speech as an opportunity to declare his love for his longtime crush, Beth Cooper (Hayden Panettiere), and his disdain for other members of his class. With his feelings firmly on the table, Denis and his best friend Rich spend the rest of the evening hanging with Beth and her two best friends, while trying to avoid a violent revenge at the hands of those Denis spurned during his speech. Based on the novel of the same name, Beth Cooper still brings the comedy in the form of first loves, car crashes, and towel snapping wars.

Where to watch I Love You, Beth Cooper: Max

EW grade: B+ (read the review)

Director: Chris Columbus

Cast: Paul Rust, Hayden Panettiere, Lauren Storm, Jack Carpenter, Lauren London, Andrea Savage, Alan Ruck

Related content: Scream VI star Hayden Panettiere worried she could no longer act after 4-year break

<i>I Love You, Man</i> (2009)

Peter Klaven (Paul Rudd) is the opposite of a toxic male. Deeply in touch with his feminine side, Peter struggles to make male friends, and after he proposes to his girlfriend Zooey (Rashida Jones), he realizes he has no one to serve as his Best Man. With the wedding fast approaching and no prospects on the horizon, Peter meets Sydney Fife (Jason Segel), and soon finds the relationship turning bromantic. Featuring 100% more Lou Ferrigno than anyone would expect to find in a rom com, I Love You, Man is the ultimate expression of the power of Paul Rudd's charisma; even at his cringiest and most pathetically earnest, you're still rooting for him to win.

Where to watch I Love You, Man: Max

EW grade: A (read the review)

Director: John Hamburg

Cast: Paul Rudd, Rashida Jones, Jason Segel, Jon Favreau, Andy Samberg, Joe Lo Truglia, Lou Ferrigno

Related content: Paul Rudd: What's not to love?

<i>Juno</i> (2008)

Every high school experience comes with bumps — but some are more visible than others. After 16-year-old Juno MacGuff (Elliot Page) accidentally becomes pregnant with her best friend Paulie Bleeker's (Michael Cera) baby, she decides to give the child up for adoption to yuppie parents Vanessa (Jennifer Garner) and Mark (Jason Bateman). But even with the begrudging support of her father and stepmother, Juno struggles to navigate this new adult world, and to decipher her ever-changing feelings for Bleeker. Penned by debut screenwriter Diablo Cody in a Minnesota Target over a seven-week period and released during 2007, a year known for its cinematic interpretations of modern pregnancy (see also: Knocked Up and Waitress), Juno is a romantic comedy that uses witticisms as weapons, parrying off feelings with banter until words are no longer strong enough to contain the deluge of earnest emotion that, in the end, carries the film. 

Where to watch Juno: Max

EW grade: A- (read the review)

Director: Jason Reitman

Cast: Elliot Page, Michael Cera, Jennifer Garner, Jason Bateman, J.K. Simmons, Allison Janney, Olivia Thirlby

Related content: Elliot Page recounts being closeted at height of Juno fame: 'That s--- literally did almost kill me'

<i>Knocked Up</i> (2007)

Based solely on the sheer number of films he wrote, directed, and produced during this period, it's reasonable to assume that Judd Apatow was responsible for at least 10% of the laughs enjoyed during the mid to late aughts. Written and directed by Apatow and released two years after the success of The 40-Year-Old Virgin, Knocked Up stars a who's who of comedy legends, past, present, and future. The film follows Alison Scott (Katherine Heigl), an up-and-coming E! News reporter, and Ben Stone (Seth Rogen), a Canadian deadbeat she meets at a Los Angeles nightclub. When a drunken hookup between the two results in an unexpected pregnancy, everyone from Ben's slacker friends to Alison's sister's family get involved as the couple decides to keep the baby and attempt to stay together. Never one to over-edit, Apatow's film runs long, but the jokes are worth it.

Where to watch Knocked Up: Max

EW grade: A (read the review)

Director: Judd Apatow 

Cast: Katherine Heigl, Seth Rogen, Jonah Hill, Jason Segel, Jay Baruchel, Martin Starr, Charlyne Yi, Leslie Mann, Paul Rudd, Maude Apatow, Iris Apatow

Related content: Katherine Heigl really delivers in Knocked Up 

<i>Marley & Me</i> (2008)

Anyone who welcomes an animal into their lives does so knowing full well how the relationship will end, but it's the journey — full of snuggles, stolen socks, and unapologetically destroyed property — that makes the inevitable tragedy worth it. Based on the 2005 bestselling book, Marley & Me had the potential to come across as a mawkish tale of puppy love, but instead is told as a heartwarming story of friendship, loss, and letting go. Featuring a uniquely restrained performance from Owen Wilson, a welcome deviation from his usual frat boy persona, Marley & Me watches as John (Wilson) and Jenny (Jennifer Aniston) grow their family, wrestle with their careers and mental health, and struggle to maintain their relationship in spite of all the responsibilities, rejections, and rewards that come with adult life. Marley & Me might be named after the film's featured pup, but this isn't the story of a dog's life: It's a story chronicling the human experience.

Where to watch Marley & Me: Max

EW grade: B+ (read the review) 

Director: David Frankel 

Talent: Owen Wilson, Jennifer Aniston, Eric Dane, Alan Arkin 

Related reading: What do we really know about Owen Wilson?

<i>Miss Congeniality</i> (2001)

Gracie Hart (Sandra Bullock) is an FBI agent with a chip on her shoulder and a gun in her holster. Married to the job and completely opposed to having a personal life, she is the agent least likely to appear in a Miss America pageant — that is, until the bureau is tasked with saving the competition from a terrorist threatening to bomb the proceedings. Forced to go undercover, Agent Hart must figure out how to reconcile her prickly personality with the pageant's saccharine approach, all while attempting to protect her fellow contestants from being blown up. A lively action comedy featuring all the best rom-com tropes, including makeover montages, choreographed dance numbers, and Michael Caine in the role of an authoritarian pageant coach, Miss Congeniality serves up a satirical look at America's obsession with beauty pageants (ahem: scholarship programs), with a side of female bonding.

Where to watch Miss Congeniality: Max

EW grade: (read the review)

Director: Donald Petrie 

Cast: Sandra Bullock, William Shatner, Ernie Hudson, Benjamin Bratt, Candice Bergen, Michael Caine

Related content: Hugh Jackman bombed his audition for the Benjamin Bratt Miss Congeniality role

<i>Pretty in Pink</i> (1986)

Classified as one of John Hughes' "Brat Pack" films, Pretty in Pink offers more than just a window into '80s high school dynamics. Molly Ringwald stars as Andie, a middle class teen living in a Chicago suburb, who falls in love with Blane (Andrew McCarthy), one of the privileged boys at her school, while her quirky friend "Duckie" (Jon Cryer) is also hot on her tail. The premise is a tale as old as time, but the film's honest depiction of class issues and adolescent insecurities — coupled with Ringwald's standout performance — made it one of Gen X's most beloved romantic comedies. Even after three and a half decades and countless cultural shifts, this film's inherent sensitivity and relatability shines through.

Where to watch Pretty in Pink: Max

EW grade: N/A

Director: John Hughes

Cast: Molly Ringwald, Andrew McCarthy, Jon Cryer, Harry Dean Stanton, Annie Potts, James Spader

Related content: EW Reunions: The Pretty in Pink cast agrees that Duckie would have come out by now

<i>Serendipity</i> (2001)

When destiny has a sense of humor, we call it serendipity, which also happens to be the title of one of 2001's most beloved romantic comedies. A whirlwind New York love story, Serendipity stars Kate Beckinsale and John Cusack as two young city dwellers who meet and enjoy a magical night — only to decide to let fate control whether they end up together.

As the years pass and their life paths diverge, it seems destiny has other plans for the would-be lovers, but New York City and a series of fortunate events may end up reuniting the pair after all. A missed connections comedy featuring an excellent supporting cast and a screenplay that is more than willing to lean into all of the best tropes of the genre, Serendipity is fun, funny, and guaranteed to make you yearn for a holiday season spent in the Big Apple.

Where to watch Serendipity: Max

EW grade: A- (read the review)

Director: Peter Chelsom

Talent: John Cusack, Kate Beckinsale, Molly Shannon, Jeremy Piven, Bridget Moynahan, Eugene Levy

Related reading: Jennifer Aniston passed on Serendipity because Friends felt like doing a rom-com every week

<i>Shiva Baby</i> (2021)

Released during the pandemic, Shiva Baby is both an indie rom-com and a delightful reminder of the emotional dangers that come with spending time in a room full of acquaintances — especially when that room includes at least two people you've slept with already. Danielle (Rachel Sennott) plays a college student and call girl who, along with her parents (Polly Draper and Fred Melamed), attends a Jewish mourning ritual held at the home of a family member. While there, Danielle finds herself caught between her past (in the form of her more successful best friend and former lover, Maya) and her present (her sugar daddy Max, who thinks she's in law school, and who brought along the wife and baby he never told her about). Based on director Emma Silegman's short by the same name, Shiva Baby is a comedy that requires the emotional fortitude of a horror film, as viewers are forced to withstand an onslaught of cringe moments. 

Where to watch Shiva Baby: Max

EW grade: B (read the review)

Director: Emma Silegman

Cast: Rachel Sennott, Polly Draper, Fred Melamed, Molly Gordon, Dianna Agron  

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<i>Singin' in the Rain</i> (1952)

Widely considered one of the best musicals ever captured on film, Singin' in the Rain has everything from music and dance to comedy and romance. Released 29 years after the entertainment industry premiered its first movie featuring sound-on-film, the story stars Gene Kelly as a celebrated silent film actor struggling to make the jump to the "talkies," and Debbie Reynolds as an up-and-coming actress trying to break into the business. The majority of the film's comedy and over-the-top dance numbers are provided by the charismatic Donald O'Connor, and Jean Hagen makes a delightful (and Oscar nominated) turn as Lina, a silent movie star with a face for film and a Brooklyn accent strong enough to stop traffic. A beloved treasure and shining representative from Hollywood's Golden Era, Singin' in the Rain continues to endure and inspire.

Where to watch Singin' in the Rain: Max

EW grade: A+ (read the review)

Director: Stanley Donen, Gene Kelly

Cast: Gene Kelly, Debbie Reynolds, Donald O'Connor, Jean Hagen

Related content: Every Singin' in the Rain reference in Babylon

<i>The Artist</i> (2011)

A triumphant return to cinema's fledgling roots, The Artist is a black and white, mostly silent film chronicling Hollywood's transition from audio-free films to "talkies." Beautifully shot, emotionally enchanting, and wildly different from any other modern romantic comedy, The Artist doesn't need sound to get its message across. Led by French actors Jean Dujardin and Bérénice Bejo, and featuring John Goodman in the role of a cigar-smoking Old Hollywood studio boss, The Artist somehow manages to feel forward-thinking and nostalgic at the same time. Undoubtedly romantic, the movie's real love affair, an EW critic writes in their review, "is the one between us, the jaded 21st-century audience, and the mechanical innocence of old movies, which here becomes new again."

Where to watch The Artist: Max

EW grade: A- (read the review)

Director: Michel Hazanavicius 

Cast: Jean Dujardin, Bérénice Bejo, John Goodman, James Cromwell, Penelope Ann Miller, Malcolm McDowell, Missi Pyle

Related content: Uggie the dog dead: Star of The Artist was 13

<i>The Last of the Blonde Bombshells</i> (2000)

A film with a sensibility that can only be described as singularly British, The Last of the Blonde Bombshells is a romantic comedy with some rhythm. Elizabeth (Judi Dench) spent World War II playing saxophone in a swing band called the Blonde Bombshells. After the death of her husband, Elizabeth reconnects with Patrick (Ian Holm) — the band's former drummer and only male member, who avoided conscription during the war by cross-dressing. After the pair start dating, Elizabeth decides to get the band back together, but discovers the Bombshells have scattered with members in jail, suffering from alcoholism, and devoted to the Salvation Army. Described by EW's reviewer as "witty and wistful," The Last of the Blonde Bombshells is another piece of evidence that blondes really do have more fun.

Where to watch The Last of the Blonde Bombshells: Max

EW grade: B+ (read the review)

Director: Gillies MacKinnon 

Cast: Judi Dench, Ian Holm, Romola Garai, Olympia Dukakis

Related content: Judi Dench says acting 'has become impossible' due to worsening eyesight

<i>The Lobster</i> (2016)

An absurdist black comedy that satirizes our culture's discomfort around uncoupled people, The Lobster asks what would happen if singles were given 45 days to find a mate, or transformed into the animal of their choice. After David's (Colin Farrell) wife leaves him, he is taken to a hotel and instructed to find someone compatible. But when an incident involving a potential life partner forces him to flee into the woods to live with the loners, David discovers that it doesn't matter where you are or who you're with — falling in love is never easy. Also starring Rachel Weisz, Ben Whishaw, John C. Reilly, and Olivia Colman, The Lobster is one of the most original romantic comedies of all time, and will live in your brain rent-free for weeks after watching.

Where to watch The Lobster: Max

EW grade: A (read the review)

Director: Yorgos Lanthimos

Cast: Colin Farrell, Rachel Weisz, Ben Whishaw, John C. Reilly, Olivia Colman, Léa Seydoux

Related content: The Lobster: Colin Farrell shares his (spoiler-free) thoughts on the film's ending

<i>The Sisterhood of the Traveling Pants 2</i> (2008)

Four best friends and the one pair of jeans that fit them all return in 2008's The Sisterhood of the Traveling Pants 2. Now having completed their first year of college, Bridget (Blake Lively), Lena (Alexis Bledel), Tibby (Amber Tamblyn), and Carmen (America Ferrera) embark on their respective summer plans, but find their friendship tested by love, loss, family, and growing pains. With storylines taking place in exotic locales (like Turkey, Greece, and New York City), and more domestic settings (like Alabama, Rhode Island, and Connecticut), The Sisterhood of the Traveling Pants 2 is a charming follow up to 2005's original film, and an oft-needed reminder that the best friendships can survive anything — even the loss of a beloved pair of pants.

Where to watch The Sisterhood of the Traveling Pants 2: Max

EW grade: B+ (read the review)

Director: Sanaa Hamri 

Cast: America Ferrera, Blake Lively, Alexis Bledel, Amber Tamblyn, Rachel Nichols, Rachel Ticotin, Shohreh Aghdashloo, Blythe Danner, Lucy Hale

Related content: Sisterhood of the Traveling Pants: A third movie could happen 'sooner rather than later'