The best holiday movies of the 2000s (that you can stream right now)

Ethan Alter
·Senior Writer, Yahoo Entertainment
·15 min read
Photo: Everett Collection
Elf, The Holiday and The Christmas Chronicles. (Photo: Everett Collection)

The holidays are here again, which means families have the chance to gather ’round the television to revisit beloved seasonal fair like Meet Me in St. Louis, A Christmas Story and Home Alone. Much as we enjoy our umpteenth viewings of those vintage favorites, the first two decades of the 21st century have gifted us with a new canon of holiday classics that have played in theaters or on streaming services like Netflix. In the spirit of the season, here’s Yahoo Entertainment’s picks for the best holiday movies released since 2000, all of which are able to stream right now. And keep in mind: As that stone-cold Christmas classic Die Hard proves, a great Christmas movie doesn’t necessarily have to be about Christmas. (Also, they don’t always have to be for kids.)

Serendipity (2001)

SERENDIPITY, Kate Beckinsale, John Cusack, 2001
Kate Beckinsale and John Cusack in Serendipity, 2001. (Photo: Miramax)

When Harry Met Sally owns New Year’s in New York, but Serendipity has Christmas on lock. Kate Beckinsale and John Cusack meet cute during a Big Apple Christmas, but can’t act on their feelings due to being in other relationships. So they go their separate ways and decide to let the universe determine their romantic fate... at least until they decide to take a more active role in finding each other again. Directed by Peter Chelsom, Serendipity is as sweet as one of the desserts served at the titular restaurant, which makes it a great movie to stream while enjoying Christmas treats. In fact, this movie is the reason why the lines are always so long at Serendipity 3.

Available to rent or purchase on Amazon.

About a Boy (2002)

ABOUT A BOY, Hugh Grant, Nicholas Hoult, 2002 (c) Universal Pictures.  Courtesy Everett Collection.
Hugh Grant and Nicholas Hoult in About a Boy, 2002 (Photo: Universal Pictures. Courtesy Everett Collection)

Christmas celebrations bracket this stellar adaptation of Nick Hornby’s terrific novel, which takes place over the course of a very eventful year. The holiday especially haunts Hugh Grant’s protagonist, Will, whose father wrote an inane, inescapable Yuletide ditty called “Santa’s Super Sleigh,” which affords his man-child son a wastrel life. But, like any good Christmas movie, Will ultimately changes for the better, thanks to his own little angel, a 12-year-old boy named Marcus (Nicholas Hoult).

Available to stream on Starz and Hulu with a Starz subscription.

Bad Santa (2003)

BAD SANTA, Billy Bob Thornton, 2003, (c) Dimension Films/courtesy Everett Collection
Billy Bob Thornton in Bad Santa, 2003. (Photo: Dimension Films/courtesy Everett Collection)

No matter how much a person loves Christmas, there comes a moment when they will absolutely lose it if they hear that freaking Mariah Carey song one more time. That’s why the world needs Bad Santa, the Grinch-iest of all Christmas movies. Terry Zwigoff’s black comedy stars Billy Bob Thornton as a thief turned department-store Santa who is also a foul-mouthed, misanthropic alcoholic. True to the Christmas spirit, he finds redemption through the love of a child (Brett Kelly), but the movie never goes soft, maintaining its icicle-sharp edge from the hilarious first scene to the last. Let’s all pretend the sequel was never made, mkay?

Available to rent or purchase on Amazon.

Elf (2003)

“Buddy the Elf, what’s your favorite color?” There are your traditional Christmas movie classics, and your contemporary Christmas movie classics, and this Jon Favreau-directed, Will Ferrell-starring gem might be the rare gift that fits in both stockings. Charting the journey of Santa’s most lovable, most ginormous helper as he leaves the North Pole for New York, it’s an uproariously funny fish-out-of-water comedy, charming family yarn, and heartfelt love letter to the Big Apple.

Available to stream on Starz and Hulu with a Starz subscription.

The Hebrew Hammer (2003)

THE HEBREW HAMMER, Adam Goldberg, 2003, (c) Strand Releasing/courtesy Everett Collection
Adam Goldberg in The Hebrew Hammer, 2003. (Photo: Strand Releasing/courtesy Everett Collection)

We’ll admit it: There aren’t enough Hanukkah-themed films on this list of “Best Holiday Movies.” That’s because there aren’t enough Hanukkah-themed films being made (or good ones anyway; sorry, Adam Sandler’s Eight Crazy Nights). Somehow this hilarious Shaft-inspired “Jewploitation” comedy about the crime-fighting “Certified Circumcised Dick” Mordechai Jefferson Carver (Adam Goldberg) has flown far under the radar, but we’re at peace with its “cult classic” status.

Available to stream on Xfinity.

Love Actually (2003)

LOVE ACTUALLY, Hugh Grant, Martine McCutcheon, 2003. © Universal/ Courtesy: Everett Collection
Hugh Grant and Martine McCutcheon in Love Actually, 2003. (Photo: Universal/ Courtesy: Everett Collection)

Although it was only a modest hit when it premiered in theaters, Love Actually has since become the gift that keeps on giving for rom-com lovers. Weaving together no fewer than 10 storylines about couples ranging from Prime Minister Hugh Grant and staffer Martine McCutcheon to widower Liam Neeson and his stepson Thomas Sangster, one could argue that Richard Curtis’s contemporary favorite is too much movie. But Love Actually’s excess is one of the things its fans adore; after all, with holiday movies — as in love — you might as well go big or go home.

Available to stream on Hulu.

Tokyo Godfathers (2003)

TOKYO GODFATHERS, Gin, Miyuki, 2003, (c) Samuel Goldwyn/courtesy Everett Collection
Tokyo Godfathers, 2003. (Photo: Samuel Goldwyn/courtesy Everett Collection)

Celebrate the holidays anime-style with the third feature from the late, great Japanese filmmaker, Satoshi Kon. Freely adapting the 1913 novel, The Three Godfathers (which later became a 1948 John Wayne Western), the film unfolds in modern-day Tokyo over the course of an eventful Christmas Eve. After finding an abandoned infant, a trio of homeless city slickers attempt to track down the child’s parents, encountering lots of adventure along the way. With its PG-13 rating, Tokyo Godfathers isn’t necessarily the kind of holiday cartoon you’d share with your little ones, but it’s a great yarn for those who have aged out of Rudolph the Red-Nosed Reindeer.

Available to stream on Crackle.

Millions (2004)

MILLIONS, Lewis McGibbon, James Nesbitt, Alex Etel, 2004, (c) Fox Searchlight/courtesy Everett Collection
Lewis McGibbon, James Nesbitt and Alex Etel in Millions, 2004. (Photo: Fox Searchlight/courtesy Everett Collection)

Danny Boyle’s underrated gem follows two brothers who stumble on a huge amount of cash that was lost after a robbery. The criminals want it back, but nine-year-old Damian (Alex Etel) believes the money is a gift from God and begins his own personal campaign to help the poor. The film’s climax is a Christmas miracle that will make even the most Scrooge-like viewer wipe away tears.

Available to stream on Disney+.

Joyeux Noel (2005)

Joyeux Noel
Joyeux Noel, 2005. (Photo: Sony Pictures Classics)

Here’s your rare Christmas story/war movie hybrid. Nominated for Best Foreign Language Film at the 2006 Academy Awards, French writer-director Christian Carion’s touching drama tells a fictionalized account of the real-life “Christmas truce” that took place among French, British and German military forces on the frontlines of World War I. Unfortunately, and in this case inevitably, truces only last so long.

Available to stream on Crackle.

The Shane Black Christmas Trilogy (2005-2016)

Shane Black Christmas Trilogy
Kiss Kiss Bang Bang, Iron Man 3 and The Nice Guys. (Photo: Warner Bros., Marvel)

It’s no secret the director is an unapologetic fan of Christmas, with the holiday playing a supporting role in all his films. Kiss Kiss Bang Bang finds desperate dad Robert Downey Jr. committing a crime to buy his kid the year’s hottest toy — an incident that launches a crazy caper involving a movie crew and gangsters. Iron Man 3 is set against the Yuletide season, finding Tony Stark adrift and leaning on a young boy (whom Black has called Tony’s “Ghost of Christmas Past”) for redemption. (Bonus: There’s this great scene with Tony dancing around his lab to the soulful strains of Joe Williams’s “Jingle Bells.”) Finally, The Nice Guys features Russell Crowe and Ryan Gosling buddying up in a retro neo-noir romp that climaxes at Christmas, minus the ribbons and bows.

Kiss Kiss Bang Bang is available to rent or purchase on Amazon; Iron Man 3 is available to stream on Disney+; The Nice Guys is available to stream on Hulu.

The Holiday (2006)

THE HOLIDAY, Kate Winslet, Jack Black, 2006. ©Columbia Pictures/courtesy Everett Collection
Kate Winslet and Jack Black in The Holiday, 2006. (Photo: Columbia Pictures/courtesy Everett Collection)

It’s an A-list Hallmark Christmas original, and we mean that in the best possible way. Writer-director Nancy Meyers doubles down and gives us two beautiful homes: the quaint English cottage and sleek L.A. mansion that two women — Kate Winslet’s heartbroken Iris and Cameron Diaz’s jilted Amanda — spontaneously swap for solo holiday vacations. Neither is looking for love, but they each find it when Jack Black and Jude Law show up on their respective doorsteps. Still, it’s the warm, supportive relationship between Iris and the aging screenwriter (Eli Wallach) who teaches her about “gumption” that turns out to be everyone’s favorite.

Available to stream on Hulu.

Inside (2007)

Beatrice Dalle in 'Inside' (Photo: Weinstein Company/courtesy Everett Collection)
Beatrice Dalle in Inside. (Photo: Weinstein Company/courtesy Everett Collection)

Warning: Even though Inside is, at heart, a Yuletide mother-and-daughter story, it’s absolutely not a movie you should watch with your mother … or your child. Julien Maury and Alexandre Bustillo’s gnarly horror story unfolds on Christmas Eve, when a pregnant widow is assaulted in her home by another woman with whom she unknowingly shares a painful history. And we do mean painful; after watching Inside, you’ll think twice about picking up a pair of scissors to open up your Christmas presents.

Available to stream on Shudder.

In Bruges (2008)

IN BRUGES, from left: Colin Farrell, Clemence Poesy, 2008. ©Focus Features/Courtesy Everett Collection
Colin Farrell and Clemence Poesy in In Bruges, 2008. (Photo: Focus Features/Courtesy Everett Collection)

The picture-perfect Belgian city is the setting for Martin McDonagh’s offbeat crime film about two hit men (Colin Farrell and Brendan Gleeson) who go into hiding after a botched kill. It may be Christmastime, but there’s no heartwarming redemption in store for Farrell, who has committed a crime he can’t forgive himself for. The darkly hilarious story builds to a stunning, violent finale in the heart of the medieval city, which looks like a miniature Christmas village come to life.

Available to rent or purchase on Amazon.

Arthur Christmas (2011)

ARTHUR CHRISTMAS, Arthur (voice: James McAvoy), 2011. ©Columbia Pictures/Courtesy Everett Collection
James McAvoy voices Arthur in Arthur Christmas, 2011. (Photo: Columbia Pictures/Courtesy Everett Collection)

Offering an entertaining glimpse behind the curtain and featuring an A-list voice cast (including James McAvoy, Hugh Laurie, Bill Nighy and Jim Broadbent), Aardman Studios’ underappreciated CG-animated feature tracks three generations of Santa Clauses in this story of how the least likely hero winds up saving the (holi)day. Arthur Christmas deserves a slot in the holiday rotation alongside the Grinch, Rudolph and Charlie Brown.

Available to stream on Starz and Hulu with a Starz subscription.

A Very Harold & Kumar Christmas (2011)

A Very Harold and Kumar Christmas
John Cho and Kal Penn in A Very Harold and Kumar Christmas, 2011. (Photo: New Line Cinema)

Released in glorious 3D in theaters, the third — and sadly final… for now — Harold & Kumar is just as funny in good old-fashioned 2D. In desperate need of a Christmastime miracle, the estranged pals (John Cho and Kal Penn) put their squabbling on hold to find a replacement for the valuable tree that Kumar burned down with a stray reefer. As always with the H&K franchise, the movie’s comic high point is Neil Patrick Harris’s self-aware cameo as the alpha male version of himself, this time leading a Christmas stage spectacular that’s trippier than anything playing at Radio City Music Hall.

Available to stream on HBO Max.

Carol (2015)

Cate Blanchett in 'Carol' (Photo: Wilson Webb/©Weinstein Company/Courtesy Everett Collection)
Cate Blanchett in Carol, 2015. (Photo: Wilson Webb/©Weinstein Company/Courtesy Everett Collection)

Set in the winter of 1952, the love story between between glamorous older woman Carol (Cate Blanchett) and young photographer Therese (Rooney Mara) begins in a garland-decked department store and unfurls across a backdrop of holiday cheer: a crackling fireplace in Carol’s tony New Jersey home, a gentle snowfall when Therese takes her first picture of Carol and shabby decorations in the lobbies of motels when the women escape the city together. Their hard-earned happy ending takes place after New Year’s Day, but at Carol’s warmly lit table in the Oak Room, it still feels like Christmas.

Available to stream on Netflix.

Krampus (2015)

KRAMPUS, l-r: Allison Tolman, Adam Scott, Toni Collette, 2015. ph: Steve Unwin/©Universal Pictures/courtesy Everett Collection
Allison Tolman, Adam Scott and Toni Collette in Krampus, 2015. (Photo: Steve Unwin/©Universal Pictures/courtesy Everett Collection)

In the grand tradition of Silent Night, Deadly Night, Black Christmas and Gremlins, Krampus delivers some Christmas-based bloodletting to break up the typical holiday treacle. Based on the Euro folk legend of a goatlike demon that feasts on the naughty list, Krampus mixes jump scares and belly laughs to delightful effect. Think of it as a different kind of holly-jolly family flick.

Available to stream on Hulu.

The Night Before (2015)

THE NIGHT BEFORE, from left: Joseph Gordon-Levitt, Seth Rogen, Anthony Mackie, 2015. ph: Sarah Shatz/©Columbia Pictures/courtesy Everett Collection
Joseph Gordon-Levitt, Seth Rogen and Anthony Mackie in The Night Before, 2015. (Photo: Sarah Shatz/Columbia Pictures/courtesy Everett Collection)

It wasn’t the box-office hit it deserved to be, but do yourself a favor and give this raunchy Christmas Eve comedy a spin this season if you missed it the first time around. Seth Rogen, Joseph Gordon-Levitt and the continually underappreciated one-man comedy act Anthony Mackie play three best buds whose annual tradition of wreaking havoc on New York City every Dec. 24 comes to an end in glorious, hilarious fashion.

Available to stream on Hulu.

Tangerine (2015)

Kitana Kiki Rodriguez and Mickey O'Hagan in 'Tangerine' (Photo: Magnolia Pictures/courtesy Everett Collection)
Kitana Kiki Rodriguez and Mickey O'Hagan in Tangerine, 2015. (Photo: Magnolia Pictures/courtesy Everett Collection)

You haven’t seen a holiday movie quite like this before: Sean Baker’s vibrant portrait of life on the streets of downtown Los Angeles stars transgender actress Kitana Kiki Rodriguez as sex worker Sin-Dee Rella, fresh out of prison on Christmas Eve and eager to track down her cheating boyfriend/pimp, Chester (James Ransone). Rowdy, rambunctious and full of heart, Tangerine is a Christmas carol for our day and age, preaching peace on earth and goodwill to all genders and races.

Available to stream on Tubi.

Almost Christmas (2016)

One year removed from the death of his beloved wife, Walter Meyers (Danny Glover) attempts to carry on the tradition of hosting a large family Christmas, but finds himself stymied by squabbling and his own latent grief. Not that Almost Christmas is in any way a mournful dirge: Thanks to an ace ensemble that includes Romany Malco, Mo’Nique and J.B. Smoove, there are plenty of laughs (and tears) to be found at this spirited family reunion.

Available to stream on Hulu.

Anna and the Apocalypse (2018)

ANNA AND THE APOCALYPSE, from left: Malcolm Cumming, Christopher Leveaux, Sarah Swire, Ella Hunt, 2017. © Orion Pictures/courtesy Everett Collection
Malcolm Cumming, Christopher Leveaux, Sarah Swire and Ella Hunt in Anna and the Apocalypse, 2017. (Photo: Orion Pictures/courtesy Everett Collection)

Sorry Jack Skellington: The Nightmare Before Christmas isn’t the only movie musical that’s perfect for both Halloween and Christmas. When zombies attack the picturesque English town of Little Haven, the local teenagers sing and slash their way through an army of the walking dead. Boasting catchy songs with titles like “Human Voice” and “What a Time to Be Alive,” Anna and the Apocalypse is light years away from from your typical brain dead zombie cash-grab.

Available to stream on Hulu.

The Christmas Chronicles (2018) and The Christmas Chronicles 2 (2020)

Who better to play Santa Claus than good ol’ Snake Plissken? Kurt Russell dons the red suit and beard of the gift-giving globetrotter in these charming Netflix fables, produced by Chris Columbus — the guy behind two of the best Christmas movies of all time: Gremlins and Home Alone. Both films feature Russell’s real-life partner, Goldie Hawn, as Mrs. Claus in a gift of casting that keeps on giving.

Available to stream on Netflix.

Shazam! (2019)

Zachary Levi in 'Shazam!' (Photo: Steve Wilkie/Warner Brothers / Courtesy Everett Collection)
Zachary Levi in Shazam!, 2019. (Photo: Steve Wilkie/Warner Brothers / Courtesy Everett Collection)

We’ve had to wait three decades since 1992’s Batman Returns for another Christmas movie set in the DC Universe. Fortunately, Shazam! is in no way a lump of coal under the proverbial tree. In fact, this is a superhero movie that very much understands the reason for the season, telling a heartfelt story of families lost and found and how the greatest present you can give someone else is your love and trust. Also super powers ... don’t forget about the super powers.

Available to stream on HBO Max.

Jingle Jangle: A Christmas Story (2020)

When Jingle Jangle director David E. Talbert couldn’t interest his son in any of his childhood film favorites, he went ahead and made a classic Christmas musical for a new generation. Forest Whitaker stars as toymaker Jeronicus Jangle, who rediscovers the magic of the season when his granddaughter joins the family business. Filled with catchy songs and great performances, Jingle Jangle is destined to be played on repeat for decades to come.

Available to stream on Netflix.

Happiest Season (2020)

Clea DuVall assembled an all-star cast for her quietly radical holiday movie — the first mainstream Christmastime rom-com to center around a lesbian couple, played by Kristen Stewart and Mackenzie Davis. While it draws on plot elements previously seen in Meet the Parents and The Birdcage, Happiest Season has a comic energy all its own, and builds to a climatic holiday party that’s both heartbreaking and hilarious. Already a viral hit on Twitter, the movie is guaranteed to keep on generating memes even after the calendar turns to January.

Available to stream on Hulu.

[Editor’s note: Earlier versions of this article was published on Nov. 29, 2017 and Dec. 12, 2019. The list has been updated with updated streaming information and some new picks.]

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