The best holiday movies of the 2000s, from 'Elf' to 'Love Actually' to 'Anna and the Apocalypse'

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From Elf to The Holiday, here are the best holiday movies of the 2000s.
Here are Yahoo Entertaiment's picks for the best holiday movies of the 2000s, including Elf, Love Actually and The Holiday. (Photo illustration: Maayan Pearl/Yahoo News; photos: Getty Images)

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 21st century has gifted us with a new canon of holiday classics. In the spirit of the season, here are Yahoo Entertainment’s picks for the best holiday movies released since 2000, all of which can be streamed right now.

Serendipity (2001)

Seredipity, starring Kate Beckinsale and John Cusack, released in 2001
Kate Beckinsale and John Cusack in Serendipity. (Miramax/Everett Collection)

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 choose 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.

Serendipity is currently streaming on Max.

About a Boy (2002)

About a Boy, starring Hugh Grant and Nicholas Hoult, released in 2002.
Hugh Grant and Nicholas Hoult in About a Boy. (Universal Pictures/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, played by future Renfield star, Nicholas Hoult.

About a Boy is currently streaming on Starz.

Bad Santa (2003)

Bad Santa, starring Billy Bob Thornton, was released in 2003.
Billy Bob Thornton in Bad Santa. (Dimension Films/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 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 just all pretend the sequel was never made.

Bad Santa is currently streaming on Paramount+.

Elf (2003)

Buddy (Ferrell) enjoys a breakfast of champions in Elf
Buddy (Will Ferrell) enjoys a breakfast of champions in Elf. (New Line/Everett Collection)

“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. We're still glad the Jim Carrey-as-Buddy thing was just a rumor.

Elf is currently streaming on Max.

The Hebrew Hammer (2003)

The Hebrew Hammer, starring Adam Goldberg, was released in 2003.
Adam Goldberg in The Hebrew Hammer. (Strand Releasing/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 — just ask Rita Moreno! 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.

The Hebrew Hammer is currently streaming on Tubi.

Love Actually (2003)

Love Actually, starring Hugh Grant and Martine McCutcheon, was released in 2003.
Hugh Grant and Martine McCutcheon in Love Actually. (Universal/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 Brodie-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.

Love Actually is currently streaming on Netflix.

Tokyo Godfathers (2003)

A scene from Satoshi Kons Yuletide anime Tokyo Godfathers.
A scene from Satoshi Kon's Yuletide anime Tokyo Godfathers. (Samuel Goldwyn/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.

Tokyo Godfathers is currently streaming on Tubi.

Millions (2004)

Millions, starring Lewis McGibbon, James Nesbitt and Alex Etel, released in 2004.
Lewis McGibbon, James Nesbitt and Alex Etel in Danny Boyle's Millions. (Fox Searchlight/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 9-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.

Millions is currently streaming on Disney+.

Joyeux Noel (2005)

A scene from the Christmastime war movie Joyeux Noel.
A scene from the Christmastime war movie Joyeux Noel. (Sony Pictures Classics/Everett Collection)

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.

Joyeux Noel is currently streaming on Tubi.

The Shane Black Christmas trilogy (2005-2016)

Shane Black Christmas Trilogy consists of Kiss Kiss Bang Bang, Iron Man 3 and The Nice Guys, all released between 2005 and 2016.
From Kiss Kiss Bang Bang to Iron Man 3 to The Nice Guys, Shane Black loves his offbeat Christmas movies. (Warner Bros., Marvel/Everett Collection)

It’s no secret that Shane Black 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 currently available to rent or purchase on Prime Video; Iron Man 3 is currently streaming on Disney+; The Nice Guys is currently streaming on Netflix.

The Holiday (2006)

The Holiday, starring Kate Winslet and Jack Black, was released in 2006.
Kate Winslet and Jack Black in The Holiday. (Columbia Pictures/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 the 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 bond between Iris and the aging screenwriter (Eli Wallach) who teaches her about “gumption” that turns out to be everyone’s favorite relationship.

The Holiday is currently streaming on Hulu.

In Bruges (2008)

In Bruges, starring Colin Farrell and Clemence Poesy, was released in 2008.
Colin Farrell and Clemence Poesy spend the holidays In Bruges. (Focus Features/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.

In Bruges is currently streaming on Starz.

Arthur Christmas (2011)

Arthur Christmas, featuring the voice of James McAvoy, was released in 2011.
James McAvoy voices Arthur in Aardman's animated favorite Arthur Christmas. (Columbia Pictures/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’s 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.

Arthur Christmas is currently available to steam on Max.

A Very Harold & Kumar Christmas (2011)

John Cho and Kal Penn in A Very Harold and Kumar Christmas.
John Cho and Kal Penn in A Very Harold & Kumar Christmas. (New Line Cinema/Everett Collection)

Released in glorious 3D in theaters, the third Harold & Kumar misadventure 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.

A Very Harold & Kumar Christmas is currently available for rent or purchase on Prime Video.

Carol (2015)

Cate Blanchett in Carol.
Cate Blanchett in Carol. (Wilson Webb/Weinstein Company/Everett Collection)

Set in the winter of 1952, the love story 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.

Carol is currently available to stream on Netflix.

Krampus (2015)

Krampus, starring Allison Tolman, Adam Scott and Toni Collette, was released in 2015.
Allison Tolman, Adam Scott and Toni Collette in Krampus. (Steve Unwin/Universal Pictures/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 from the same writer/director who turned a pumpkin-masked boy into a Halloween icon.

Krampus is currently streaming on Peacock.

The Night Before (2015)

The Night Before, starring Joseph Gordon-Levitt, Seth Rogen and Anthony Mackie, was released in 2015.
Joseph Gordon-Levitt, Seth Rogen and Anthony Mackie in The Night Before. (Sarah Shatz/Columbia Pictures/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.

The Night Before is currently streaming on Tubi.

Tangerine (2015)

Kitana Kiki Rodriguez and Mickey O'Hagan in Tangerine.
Kitana Kiki Rodriguez and Mickey O'Hagan in Tangerine. (Magnolia Pictures/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.

Tangerine is currently streaming on Mubi.

Almost Christmas (2016)

The cast of the 2016 holiday comedy, Almost Christmas.
The cast of 2016's Almost Christmas. (Universal/Everett Collection)

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.

Almost Christmas is currently streaming on Peacock.

Anna and the Apocalypse (2018)

Anna and the Apocalypse, starring Malcolm Cumming, Christopher Leveaux, Sarah Swire and Ella Hunt, was released in 2018.
Malcolm Cumming, Christopher Leveaux, Sarah Swire and Ella Hunt in Anna and the Apocalypse. (Orion Pictures/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 your typical brain-dead zombie cash grab.

Anna and the Apocalypse is currently streaming on AMC+

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

Real-life couple Goldie Hawn and Kurt Russell play Mrs. and Mr. Santa Claus in The Christmas Chronicles 2.
Real-life couple Goldie Hawn and Kurt Russell play Mrs. and Mr. Santa Claus in The Christmas Chronicles 2. (Netflix/Everett Collection)

Who better to play Santa Claus than good ol’ Snake Plissken? Kurt Russell dons the red suit and beard of the gift-giving globe-trotter 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.

The Christmas Chronicles movies are currently streaming on Netflix.

Shazam! (2019)

Zachary Levi in Shazam!
Zachary Levi suits up as a Christmastime superhero in Shazam!. (Steve Wilkie/Warner Brothers/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.

Shazam! is currently streaming on Max.

Jingle Jangle: A Christmas Journey (2020)

Anika Noni Rose and Forest Whitaker in a scene from Jingle Jangle.
Anika Noni Rose and Forest Whitaker in a scene from Jingle Jangle: A Christmas Journey. (Netflix/Everett Collection)

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.

Jingle Jangle is currently streaming on Netflix.

Happiest Season (2020)

Kristen Stewart and Mackenzie Davis in Happiest Season.
Kristen Stewart and Mackenzie Davis in Happiest Season. (Lacey Terrell/Hulu/Everett Collection)

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 climactic holiday party that’s both heartbreaking and hilarious. The movie is guaranteed to keep on generating memes even after the calendar turns to January.

Happiest Season is currently streaming on Hulu.

8-Bit Christmas (2021)

Sophia Reid-Gantzert and Neil Patrick Harris in 8-Bit Christmas.
Sophia Reid-Gantzert and Neil Patrick Harris in 8-Bit Christmas. (Sabrina Lantos/Warner Bros./Everett Collection)

Clearly designed like A Christmas Story for '80s babies, the yuletide comedy is told in flashbacks as a dad (Neil Patrick Harris) recounts his action-packed adventures in attempting to score a Nintendo for Christmas. It’s whip-smart, super funny and deeply poignant, and well worth seeking out every holiday season.

8-Bit Christmas is currently streaming on Max.

Christmas With You (2022)

Aimee Garcia as Angelina, Freddie Prinze Jr. as Miguel, Deja Cruz as Cristina and Zenzi Williams as Monique in Christmas With You.
Aimee Garcia and Freddie Prinze Jr. star in Christmas With You. (Jessica Kourkounis/Netflix)

Netflix has a gift for Freddie Prinze Jr. stans. The former teen heartthrob headlines his first Christmas movie ... and the first film where he gets to lean into his Latino heritage in a major way. Prinze plays a single dad who makes a Christmastime romantic connection with a pop star (Aimee Garcia) in need of a fresh start. It's not the most groundbreaking story, but Prinze and Garcia are a delightful couple-to-be and the holiday vibes are seasoned just right. Keep making movies like this and we'll happily spend another Christmas with you, Freddie.

Christmas With You is currently streaming on Netflix.

The Holdovers (2023)

Dominic Sessa, Paul Giamatti and DaVine Joy Randolph in The Holdovers.
Dominic Sessa, Paul Giamatti and Da'Vine Joy Randolph in The Holdovers. (Focus Features/Everett Collection)

Bah, humbug! When we first meet Barton Academy professor, Paul Hunham (Paul Giamatti), in Alexander Payne's '70s-era drama, he seems like a real Scrooge. But when he's tasked with babysitting the lone student (Dominic Sessa) with no place to go for Christmas, the vulnerable human beneath the prickly exterior slowly emerges. Filled with on-point period touches and a spirit of goodwill toward men and women alike, The Holdovers seems likely to endure as a seasonal favorite.

The Holdovers is currently playing in theaters and is available for rent or purchase on Prime Video

[Editor’s note: Earlier versions of this article were published on Nov. 29, 2017, Dec. 12, 2019, Dec. 10, 2020 and Dec. 9, 2022. The list has been updated with new streaming information and some new picks.]

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