The Best Holiday Movies and TV Specials to Watch This Season

The Best Holiday Movies and TV Specials to Watch This Season

Whether you’re traveling or bored at Aunt Tilly’s house this season, these films are sure to make you feel at home for the holidays. With streaming services, you can go beyond the standard Christmas movies and add new soon-to-be-classics or old TV favorites to your yearly list. We have your cheat sheet for the most festive movies, holiday specials and TV episodes that are sure to please the entire family. Wherever you may be, light a fire, cozy up with your loved ones and dive into this ultimate holiday movie list.

Classics

Streaming on Hulu and Prime Video.

This list would not be complete without including the best holiday movie of all time. Although this film is now well regarded as a classic, it received little fanfare in its initial box office release. Subsequent years have proven the timelessness of director Frank Capra’s story. Jimmy Stewart wows as George Bailey, a man who has given up on life and his on-screen chemistry with costar Donna Reed makes for one of cinema’s most captivating romances. 

Miracle on 34th Street (1947)

Streaming on Disney+, Hulu and Prime Video.

Another 1940s Christmas classic, Miracle on 34th Street sees Kris Kringle hired to play Santa Claus at New York City’s 34th Street Macy’s. Christmas magic faces off against the American legal system as Kringle must prove in court that he is the real Santa Claus. Maureen O’Hara and John Payne share the screen as Kringle’s defense, and a young Natalie Wood plays Susan, a girl resolved in her belief in Santa Claus. The 1994 remake of this film features Mara Wilson (of Matilda fame) in Wood’s role, and it can be streamed on Hulu.

White Christmas (1954)

Streaming on Netflix and Sling TV.

White Christmas follows the tale of two war buddies chasing after a pair of singing sisters, and it features the eponymous classic holiday song, crooned by Bing Crosby himself. This beloved 1954 classic has a crooner and a hoofer (Crosby again, this time with Danny Kaye stepping in at the last minute for Donald O’Connor) joining up with a sister act to perform in rural Vermont. Our boys plan a yuletide miracle to save the place, with some of the best musical numbers an uncredited Bob Fosse could put together. It also marks the only time on film when prolific Crosby breaks up, laughing so hard at Danny Kaye in their “Sisters” partial drag number that director Michael Curtiz could not get a straight take from him, so he left in the shot of Crosby completely cracking up with laughter. This was from the crooner who could play it straight in all those “road” movies with hope!

Streaming on YouTube, Tubi, Sling TV, STARZ and Hulu.

This timeless Dickens’ tale might be the most frequently adapted Christmas story on this list. Among its many cinematic iterations, the 1984 version with George C. Scott is a firm favorite. For a classic film lover, 1951’s Scrooge may satisfy, while modern-minded viewers can turn to the animated Disney adaptation from 2009.

A Christmas Story (1983)

Streaming on Sling TV, Hulu, Max and Prime Video.

This nostalgic 1980s flick is a long-time favorite. Set in 1940s Indiana, the film depicts young Ralphie Parker’s campaign to get a Red Ryder BB gun for Christmas. Childhood whimsies are bookended by dry narration from adult Ralphie as voiced by Jean Shepherd, whose life story loosely inspired the film. A Christmas Story is unmistakably ’80s, especially when looking at Mrs. Parker’s anachronistic perm or the final scene’s unfortunate depiction of a Chinese restaurant. Nevertheless, Ralphie’s endearing and enduring journey through the holiday season will have you alternately in stitches and in tears.

Comedy

Christmas with the Kranks (2004)

Streaming on Prime Video, Sling TV and AMC+. 

In this hairbrained comedy, Tim Allen and Jamie Lee Curtis play empty nesters who have to pull together a last-minute Christmas. This film will resonate with parents sick of spending big for the holidays, but ultimately it upholds the values of family and charity during the season. Chris Columbus wrote the screenplay, making Christmas with the Kranks his first appearance on this holiday movie list — and trust me, there will be more!

National Lampoon’s Christmas Vacation (1989)

Streaming on Max and Hulu. 

Yule crack up! That’s the tagline of this holiday favorite, where Chevy Chase is back again on family vacation. As always, Chase plays Clark Griswold, the hapless patriarch trying to provide the perfect holiday for his wife and kids. Follow the descent into comical chaos as the family’s plans inevitably go up in flames. 

Love, Actually (2003)

Streaming on Netflix.

This British ensemble rom-com from the creators of Bridget Jones’s Diary is a feel-good romantic holiday movie to the max. From the British prime minister to a fading rock star, from a young boy to a philandering husband, we meet a varied group approaching Christmastime. The all-star cast vies with It’s a Mad, Mad, Mad, Mad World as one that could not be put together today. Colin Firth, Liam Neeson, Emma Thompson, Hugh Grant, Kiera Knightley and Alan Rickman portray just a few of the characters who touch our hearts in this irresistible romantic comedy drama. It also contains that rarity: an enormously happy ending reminding us that love is all around.

Elf (2003)

Streaming on Max.

Will Ferrell is as funny as ever playing Buddy, a child raised as one of Santa’s elves who sets off to meet his biological father in New York City. Trying to find his place in the world, Buddy’s enthusiasm clashes with constant humbug in the big city. Still, Buddy’s festive optimism remains resilient and even contagious for those of us needing a dose of holiday spirit. 

Home Alone (1990)

Streaming on Disney+, STARZ and Hulu. 

It’s Christmas when the McCallisters leave Kevin alone for the holidays, and there’s no more entertaining viewing than watching him outsmart the pair of dopey crooks who attempt to break into his family’s house. Chris Columbus directs and John Hughes writes this holiday staple, brought to life by the physical comedy of Joe Pesci and Daniel Stern as battered thieves. The late John Candy also makes a cameo, delivering an entirely improvised performance opposite Catherine O’Hara as Kevin’s mom.

Scrooged (1988)

Streaming on Paramount+, SlingTV and Prime Video. 

I’ve spent a life in broadcasting, so of course I would enjoy a movie about Scrooge being a cruel television executive. In the film, Scrooged, he is visited by three ghosts who give him a chance to reevaluate himself. This movie reminds us of the subjective nature of comedy and drama. The late Roger Ebert told me it was his idea of the worst Christmas movie ever made. Bill Murray made this after Ghostbusters, so it was the beginning of him going on to become a leading man. Groundhog Day, anyone? – Jan Wahl

What’s Cooking? (2000)

Streaming for free on YouTube, Tubi, Prime Video, Pluto TV and the Roku Channel. 

Pass the kugel, spring rolls, tamales and outrageous conversation for a look at culturally diverse holiday celebrations. What’s Cooking? takes us to Los Angeles with gatherings that include African American, Jewish, Latino and Vietnamese families, with each culture’s food being a vehicle for family togetherness. There are tricky, sometimes hilarious, situations to feast on. Not enough people know this spicy, smart and succulent film. 

Thrillers

Die Hard (1988)

Streaming for free on YouTube and Tubi. Also available on Hulu. 

Whether this film qualifies as a holiday movie is a hotly debated subject. Die Hard, with its countless sequels and spin-offs, exists in a genre of its own. Bruce Willis undoubtedly saves Christmas in this tense thriller where he faces off against Alan Rickman’s evil Hans Gruber. Fun fact: in 2007, Bruce Willis donated his character John McClane’s undershirt to the Smithsonian.

The Apology (2022)

Streaming on Hulu and AMC+, plus available to rent from Prime Video, Redbox and Apple TV. 

This unnerving Hulu original revolves around Darlene Hagan, a mother still grieving the loss of her daughter who went missing twenty years prior. When Darlene’s estranged brother-in-law appears at her house on Christmas Eve, Darlene must grapple with the pain and secrets that arose when her daughter disappeared. Anna Gunn, well-known for her role as Skyler White in “Breaking Bad”, delivers yet another raw performance in this psychological thriller.

Krampus (2015)

Streaming on Peacock and Hulu, plus available to rent from YouTube, Apple TV and Prime Video.

Folklore comes to life when the ancient Bavarian Christmas demon torments the Engel family, a dysfunctional bunch struggling to put together a pleasant holiday. At once a meme and memorable horror-comedy flick, Krampus features a cast of familiar faces, including Adam Scott and Toni Collette. 

TV Must-Sees

How the Grinch Stole Christmas (2000)

Available to rent from Prime Video, YouTube, AppleTV, Google Play and more. 

The beloved children’s book gets a feature-length adaptation in this live-action comedy with an uncanny, incredibly green Jim Carrey as the titular curmudgeon. This iteration depicts the Grinch’s backstory, explaining how his heart became so small before retelling the classic heartwarming ending. Carrey’s Grinch makeup is reason enough to watch — it was apparently so onerous that he consulted a CIA agent for torture-resistance techniques to withstand its weight!

The Christmas Chronicles (2018)

Streaming on Netflix.

We’re betting this recent holiday film, produced by Chris Columbus and starring Kurt Russell as Old St. Nick, will quickly become a classic. Two siblings put out the cookies and turn on the camcorder in a plot to catch Santa Claus coming down their chimney. Follow them on their quirky Christmas romp by streaming The Christmas Chronicles on Netflix. 

Streaming on YouTube and Apple TV.

One the kids will love to watch, and one the adults will love to get nostalgic over. This television special focuses on Rerun, Linus and Lucy’s younger brother, who (as the title suggests) wants a dog for Christmas, Charlie Brown! This special reprises some of Vince Guaraldi’s classic Peanuts songs and will surely cure your craving for more of Charles Schultz’s famous characters. 

Streaming on YouTube, Amazon and Vudu, or you can catch it airing on cable channels like Freeform throughout December. 

Well-known and well-loved, this 1960s television special is a marvel of stop-motion animation and a timeless retelling of the Christmas carol.

Dash and Lily (2020)

Streaming on Netflix.

Two teenagers, Dash and Lily, form a connection by passing notes in this sweet romantic comedy series from Netflix. Cozy up with your boo or pop some popcorn for this warm jaunt through the holiday season.

TV Must-Sees

Streaming on Max and Hulu Premium. 

There are many Friends holiday episodes to pick from and this tops the list as our favorite. Who could forget Santa’s Tex-Mex friend, the Holiday Armadillo?

Streaming on Netflix.

Name me one other sitcom that spawned its own holiday. This Seinfeld episode sees George Costanza begrudgingly relive his father’s anti-holiday holiday, Festivus. Jerry Stiller is hysterical as George’s father, and the episode’s iconic festivities have even inspired real-world celebrations around the Festivus pole.

Streaming on Netflix.

Bill Murray, his celebrity friends and lots of singing! Cameos include George Clooney, Chris Rock, Amy Poehler, Maya Rudolph, Miley Cyrus and many more, with arthouse darling Sofia Coppola directing the special.

Streaming on Peacock.

In a fan favorite episode of The Office, Michael makes the team play “Yankee Swap” with their Secret Santa gifts.

Streaming on Peacock.

Ultimate gift-giver Leslie gets the best gift ever in this favorite episode.

Who’s writing these?

Meet our always-hungry team of foodies who compiled this list.
Please let us know if we’ve missed your favorite eat@localgetaways.com.

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