Few things evoke the joy of the holiday season quite like a great holiday movie. The best classic Christmas and New Year’s films capture the magic — and even the melancholy — that often accompanies this time of year. Holiday classics offer a window into the past while showcasing how stories about Christmastime are timeless, making this a wonderful opportunity for those new to old movies to immerse themselves.
Shutterstock: Lysenko AndriiWhite Christmas (1954)
“White Christmas” combines dazzling Technicolor with timeless tunes and spectacular dancing. Starring Bing Crosby and Danny Kaye as a song-and-dance duo and Rosemary Clooney and Vera-Ellen as a sister act, this beloved movie musical continues to shine 70 years later. Overflowing with holiday spirit, the film follows this talented group as they rally to help their former WWII general by staging a Christmas show to save his struggling Vermont inn from a snowless holiday season.
Where To Stream: Prime Video
Holiday (1938)
Katharine Hepburn and Cary Grant star in this thoughtful holiday gem about love, ambition, and societal expectations. Engaged to marry a socialite from a wealthy family, Grant discovers that her vision for their future isn’t what he wants out of life. He does, however, find a kindred spirit in Hepburn, his fiancée’s free-spirited sister. More wistful than their screwball comedies, this Hepburn/Grant pairing is a Christmas and New Year’s movie about finding joy on your own terms.
Where To Stream: Prime Video
Meet Me in St. Louis (1944)
This Technicolor movie musical is about a year in the life of the Smith family, leading up to the 1904 World’s Fair. While “Meet Me in St. Louis” covers every season, it especially resonates now. After all, it did introduce Judy Garland’s bittersweet “Have Yourself a Merry Little Christmas.” Even though it’s perfect at Christmas, we’d be remiss not to mention its spooky Halloween sequence that beautifully captures childhood fears. At any time of year, this gem still radiates warmth 80 years on.
Where To Stream: Max
Remember the Night (1940)
“Remember the Night” is a romantic comedy about the holiday spirit bringing people together — even in the most unlikely circumstances. You see, Fred MacMurray plays an assistant district attorney tasked with prosecuting a shoplifter, played by Barbara Stanwyck, on Christmas Eve. So that she doesn’t have to spend the holidays behind bars, he bails her out and things go from there. For more of Stanwyck’s charm, don’t miss her other holiday classic, “Christmas in Connecticut” (1945).
Where To Stream: Plex
Desk Set (1957)
“Desk Set” is a charming romantic comedy that today’s audiences may find surprisingly relevant. The film stars Katharine Hepburn as the head of a television network’s reference department and Spencer Tracy as an efficiency expert. When he shows up with a dreaded computer, her team begins to worry about their jobs — echoing the AI anxieties of today. Much of this takes place at Christmastime, complete with a festive mid-century office holiday party.
Where To Stream: Prime Video
It’s a Wonderful Life (1946)
While you’ve probably watched “It’s a Wonderful Life,” there’s a decent chance it was on network TV with people coming in and out of the room — and maybe even more as background noise. But that experience doesn’t do George Bailey’s journey from despair to gratitude justice. Starring James Stewart, Henry Travers, and Donna Reed, “It’s a Wonderful Life” is a moving story of community and the ripples our lives have on others. This Frank Capra Christmas classic is well worth your undivided attention.
Where To Stream: Plex
Miracle on 34th Street (1947)
If you haven’t watched “Miracle on 34th Street” since childhood, it’s time to revisit this holiday staple. Challenging skepticism and celebrating the magic of believing, it’s about a department store Santa who claims to be the real deal. Edmund Gwenn brings so much magic to the role of Kris Kringle that it’s easy to see why he won the Oscar. Through him, we’re reminded — as are a single mother and her daughter, played by Maureen O’Hara and a young Natalie Wood — that Christmas is a frame of mind.
Where To Stream: Disney+ and Paramount+
The Apartment (1960)
Starring Jack Lemmon and Shirley MacLaine, “The Apartment” is a romantic dramedy that captures the melancholy that sometimes accompanies the holiday season. Written and directed by Billy Wilder, it’s a poignant and funny movie about an insurance clerk who lets his bosses use his apartment for their romantic trysts. With a wild mid-century office holiday party and one of the most memorable New Year’s Eve sequences, “The Apartment” is a bittersweet gem.
Where To Stream: Freevee
The Bishop’s Wife (1947)
If you’re in the mood for a dash of romantic fantasy this holiday season, there’s nothing better than “The Bishop’s Wife.” Cary Grant charms as an angel who helps a struggling bishop and his wife — played by David Niven and Loretta Young — rediscover their priorities in this enchanting classic about the true meaning of Christmas. A beautiful reminder that faith, love, and kindness are the greatest gifts of all, “The Bishop’s Wife” is a magical blend of whimsy and wisdom.
Where To Stream: Freevee and Peacock
The Shop Around the Corner (1940)
Leading up to the holiday season, “The Shop Around the Corner” follows two feuding co-workers who, unbeknownst to each other, fall in love as anonymous pen pals. If that premise sounds familiar, it’s probably because you’ve seen Nora Ephron’s beloved “You’ve Got Mail” (1998), a loose adaptation. Proving how satisfying the premise is, “In the Good Old Summertime” (1949) is a charming musical remake starring Judy Garland. Don’t let the name fool you — it’s also a wonderful Christmas watch.
Experience the Holidays Through Classic Movies
Classic holiday films remind us why this season is so special. They celebrate the magic of believing, the power of generosity, and the connections that make this time of year meaningful. Offering a moment of reflection, they remind us that the holidays are an opportunity to take stock of what truly matters — love, kindness, and the impact we have on others. Let their magic transport you and remind you of what the holidays are truly about.
