20 Holiday Movies to Watch This Season, From Classics to Indies

living room decorated for christmas

Design: Emily Henderson Design, Photo: Sara Ligorria-Tramp

While everyone has their unique favorite traditions when it comes to annual end-of-year festivities, one we can probably all agree on is holiday movies. No matter your motion picture predilections during the regular calendar year, now is the time to watch and re-watch some of cinema's most heartfelt holiday flicks. From the classics to the blockbuster hits to indies, there's a resonant film for everyone. Here are our 20 holiday movie picks to stream this season.

01 of 20

The Holiday (2006)

The Holiday movie poster

Columbia Pictures 

From Nancy Meyers comes this holiday romance movie about two women who each find love through a home exchange over the holidays. Two of our favorite lines from the film are "Shall I make us a little Christmas fettuccine?" and "I like corny. I'm looking for corny in my life." The Holiday is an utterly delightful and decadently stylish romp through two whirlwind courtships. This charming flick features A-list cast members Cameron Diaz, Jude Law, Kate Winslet, and Jack Black.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

02 of 20

Carol (2015)

Carol movie poster

 The Weinstein Company

If you haven't seen this period piece starring Rooney Mara and Cate Blanchett, definitely add it to your holiday watch list. Not only is Carol thematically evolutionary, but the cinematography also makes it a treat for the eyes.

It's about two women, Therese and Carol, who navigate the complexities of love and relationships in Manhattan circa the 1950s.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu

03 of 20

Rent (2005)

Rent movie poster

Columbia/Revolution, Universal Pictures 

Set during the AIDS epidemic of the 1990s, a band of New Yorkers sing of their struggles with careers, love, life, and loss. The film is an adaptation of the Pulitzer- and Tony-winning musical, starring Idina Menzel, Anthony Rapp, Rosario Dawson, Tracie Thomas, and more. If you're in the mood for a tear-jerker, this will not disappoint.

This flick has an absolutely incredible soundtrack, so before watching the movie, download the album (from either the broadway show or the film) and try to memorize the words so you can sing along as you watch. 

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

04 of 20

Bridget Jones's Diary (2001)

Bridget Jones's Diary movie poster


Singletons will take solace in the lead heroine's humiliating yet ultimately hopeful journey through a minefield of family gatherings, career dramas, and dating fiascos. Starring Colin Firth in a tacky reindeer jumper and spanning a full year from one New Year's Eve to the next, it is the perfect all-encompassing romance to carry you into the New Year.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

05 of 20

Last Holiday (2006)

Last Holiday movie poster

Paramount Pictures 

When Georgia Byrd (Queen Latifah) learns she doesn't have much time left to live, she throws her overly cautious life to the wind and embarks on an international journey to milk what life she has left. In Europe, she charms a popular chef (Gérard Depardieu), but what will happen between her and her longtime love interest from back home?

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

06 of 20

White Christmas (1954)

White Christmas movie poster

 Robert Emmett Dolan

War buddies Bing Crosby and Danny Kaye tap-dance their way through New England's winter playground in this classic holiday film. White Christmas is chock-full of extravagant dance numbers and Irving Berlin gems like "White Christmas" and "Blue Skies." It's arguably the only time a man has ever serenaded a woman in her pajamas fireside (over liverwurst sandwiches and buttermilk) about insomnia.

Available on: Amazon Prime Video, Google Play, Vudu, YouTube

07 of 20

Love Actually (2003)

Love Actually movie poster

 NBC Universal

The debate over whether Love Actually is, in fact, the most romantic movie continues to rage. Nevertheless, the film remains a well-crafted tale of multiple love stories, set against a holiday backdrop of glowing lights and cheerful set pieces. You can't beat Keira Knightley in winter-white knitwear or Bill Nighy jingle bell-rocking out to treacly Christmas anthems.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

08 of 20

Serendipity (2001)

Serendipity movie poster


Perhaps the best thing to ever come out of a fight over the last available Christmas gift at Bloomingdale's, this John Cusack and Kate Beckinsale romantic comedy is warm, cozy, and sweet like hot cocoa. Get ready for flirtatious ice-skating scenes, prominent David Gray needle drops, and crush-worthy banter in a plot that centers around the premise that love is fate incarnate.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

09 of 20

It's a Wonderful Life (1946)

It's A Wonderful Life movie poster

Paramount Pictures 

It's a Wonderful Life is Frank Capra's beloved tale of a man who loses his inner compass and finds his way back again. Jimmy Stewart's famously amorous speeches in which he promises to lasso the moon for his one true love and later condemns plastics, ground floors, and marriage (in that order) are the ultimate in silver-screen soliloquizing.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu

10 of 20

Nothing Like The Holidays (2008)

Nothing Like The Holidays movie poster

Overture Films 

Perhaps for the final time, disparate members of the Rodriguez family come together over the Christmas season. As the movie unfolds, we learn that one brother still has feelings for a former love, while another struggles to find balance in his marriage. Then, matriarch Anna announces she intends to divorce their father.

Available on: Amazon Prime Video, iTunes, Vudu

11 of 20

The Family Stone (2005)

The Family Stone movie poster

20th Century Fox

The Family Stone is easily a romantic holiday-themed favorite. We also feel like we owe this fictional family a big thank-you for inadvertently preparing us for our own in-law encounters and family drama.

Everything seems fine and dandy until one of the sons brings homes his new girlfriend, played by Sarah Jessica Parker, who manages to serve up some Carrie Bradshaw-worthy one-liners throughout the film. It's safe to say the rest of the family isn't exactly a fan of hers.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

12 of 20

Metropolitan (1990)

Metropolitan movie poster


Whit Stillman's classic indie, Metropolitan, centers around a group of young socialites in Manhattan during the thick of debutante season (December). The group is thrown off when an outsider joins their evening conversations about love, honor, and other philosophical notions. It's a social critique and character study full of hilarious irony—and romance, of course.

Available on: iTunes, Amazon Prime Video, Hulu

13 of 20

Die Hard (1988)

Die Hard movie poster

 20th Century Fox

A tale of divorce and reconciliation amid terrorist threats on Christmas Eve, this shoot-'em-up action flick offers up loose-cannon cop-off-duty John McClane (Bruce Willis) as its holiday hero. It's a catchphrase-ridden, fully loaded adventure that begs the question: Can a man battle terrorists and save his estranged marriage in the same night?

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

14 of 20

The Preacher's Wife (1996)

The Preacher's Wife movie poster

Touchstone Pictures 

Do you love the classic Cary Grant film The Bishop's Wife? The black-and-white '40s film casts dreamy gentleman Cary Grant as an angel on earth, which seems not too far of a stretch for the devilishly handsome icon.

But we love this 1996 remake starring Denzel Washington and Whitney Houston. Buoyed by the debonaire charisma of Washington and Houston, its sweet story—which emphasizes the importance of family values above money and ambition—is entirely charming and appropriate for all ages.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

15 of 20

Four Chistmases (2008)

Four Christmases movie poster

 Metropolitan Film Studios; Warner Bros.; New Line Cinema

Has there ever been a better onscreen match than Vince Vaughn and Reese Witherspoon? In this hilarious romantic comedy, the pair is happily in love and unmarried, a lifestyle choice they choose to avoid their parents' fate. When they're forced to cancel a holiday vacation in the tropics and visit all four of their eccentric family events instead, mishaps and hilarity ensue.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

16 of 20

Memories of Christmas (2018)

Memories of Christmas movie poster


Noelle is back in her hometown in Michigan to sell her late mother's house, and to attend the holiday gala she founded years ago, which happens to take place in the lodge she intends to sell. When she meets the professional decorator who's been sprucing up the house all of these years and cancels the arrangement, he refuses. Memories of Christmas is one of several 2018 holiday movies from Hallmark that star historically underrepresented people of color.

Available on: Philo

17 of 20

Scrooged (1988)

Scrooged movie poster

 Paramount Pictures

Bill Murray brings sarcasm and wit to this 1988 modern take on Charles Dickens's A Christmas Carol. As a rich, powerful, and cold-as-ice TV executive who routinely gifts his only living relative with a company bath towel for Christmas, Murray is in top form, maneuvering his way through Christmases past, present, and future to eventually reunite with the one who got away (played by the excellent Karen Allen).

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

18 of 20

Just Friends (2005)

Just Friends movie poster

Warner Bros. 

Chris Brander (Ryan Reynolds) has slimmed down and grown up to become a successful record producer, but his high school anxieties from being an overweight and dorky teen come back to haunt him when he travels to his hometown in New Jersey. There, he crosses paths with his longtime crush and best friend, Jamie Palamino (Amy Smart). His attempts to finally win her heart get complicated when a tone-deaf pop star he's supposed to be babysitting (Anna Faris) gets involved.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, Philo

19 of 20

While You Were Sleeping (1995)

While You Were Sleeping movie poster

 Hollywood Pictures

Sandra Bullock, decked to the gills in on-trend '90s sweaters, falls for Bill Pullman in this family comedy of mistaken identity. A whimsical love story, the film is often credited alongside Speed with launching Bullock to superstardom.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

20 of 20

A Very Harold & Kumar Christmas (2011)

A Very Harold & Kumar Christmas movie poster

 Warner Bros.

It's the holiday season, and Cho and Penn are each prepping for festivities with a new circle of friends. A mysterious package reunites Cho and Penn for another raunchy, wild adventure, years after we last left them.

Available on: Amazon Prime Video, Google Play, iTunes, Vudu, YouTube

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