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Classic Holiday Movies for Winter Movie Nights

6 minute read

By Katie Ormsby

The holidays bring a special kind of magic that’s perhaps best captured on film. Holiday movies, after all, beautifully remind us to be kind and generous. Old holiday movies offer a window into the past while showcasing how stories about this time of year are timeless, making this a wonderful opportunity for those new to old movies to immerse themselves. If you’re planning a cozy movie night, an online search can help you discover holiday classics.

Shutterstock: Lysenko Andrii

White Christmas (1954)

“White Christmas” is a Technicolor marvel featuring Bing Crosby and Danny Kaye. It’s a musical filled with charm, humor, and, of course, the iconic song crooned by Bing Crosby. While the song may have been introduced in “Holiday Inn” (1942), “White Christmas” firmly has our hearts. Crosby and Kaye play a song-and-dance duo who join forces with a sister act, played by Rosemary Clooney and Vera-Ellen. The film’s colorful visuals and memorable song-and-dance numbers create a festive atmosphere.1

Remember the Night (1940)

“Remember the Night,” a romantic comedy starring Barbara Stanwyck and Fred MacMurray, is a hidden gem among holiday classics. It’s a beautiful portrayal of how the holiday spirit can bring people together, even in the most unlikely circumstances. You see, MacMurray plays an assistant district attorney tasked with prosecuting a shoplifter, played by Stanwyck, on Christmas Eve. So that she doesn’t have to spend the holidays behind bars, he bails her out, and through circumstances, they spend the holidays together.2

Meet Me in St. Louis (1944)

“Meet Me in St. Louis” is a lovely showcase for Judy Garland. It’s a musical about a year in the life of the Smith family, leading up to the 1904 World’s Fair. While it covers every season, it especially resonates this time of year. After all, the film is known for Garland’s debut of the bittersweet “Have Yourself a Merry Little Christmas.” Even though the film’s winter section is its most enduring, we’d be remiss not to mention the spooky Halloween sequence that beautifully captures childhood fears. Margaret O’Brien makes this chapter of the movie sing.3

Holiday (1938)

“Holiday,” a romantic comedy starring Katharine Hepburn and Cary Grant, is a charming and insightful classic for Christmas and New Year’s. It tells the story of a man who falls in love with his fiancée’s free-spirited sister, exploring societal expectations and the pursuit of happiness. While Hepburn and Grant are known for their screwball comedies like “Bringing Up Baby” (1938) and “The Philadelphia Story” (1940), this movie brings the pairing together for a romantic comedy that’s a little more serious and wistful.4

Miracle on 34th Street (1947)

Perhaps the most quintessential classic Christmas movie, “Miracle on 34th Street” captures the beauty of childhood wonder and the spirit of Christmas, challenging skepticism and celebrating the magic of believing. Maureen O’Hara, Edmund Gwenn, and a young Natalie Wood bring to life a story centered around a department store Santa claiming to be the real Santa Claus. The film was nominated for Best Picture and Gwenn won an Oscar for his iconic turn as Kris Kringle. If you haven’t watched “Miracle on 34th Street” since childhood, it’s time to revisit it.5

The Apartment (1960)

“The Apartment,” starring Jack Lemmon and Shirley MacLaine, 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 tale about love, morality, and ambition that follows an insurance clerk who lets his bosses use his apartment for their romantic trysts. Featuring an unforgettable mid-century holiday office party, this one’s perfect for “Mad Men” fans. It also has one of the most memorable New’s Year Eve sequences.6

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 this Oscar-nominated classic justice. Starring James Stewart, Henry Travers, and Donna Reed, “It’s a Wonderful Life” is a moving story of community and friendship. Despite a seemingly heavy premise, the movie is magical, romantic, and life-affirming.7 Make it a Frank Capra double feature with Meet John Doe (1941).8

Desk Set (1957)

“Desk Set” is a charming romantic comedy that audiences may find surprisingly relevant. Written by Phoebe and Henry Ephron, Nora Ephron’s parents, the film stars Katharine Hepburn as the head of a television network’s reference department. Spencer Tracy, an efficiency expert, shows up with a dreaded computer. As you might expect, this development causes the team to worry about their jobs — much like the AI anxieties of today. All of this takes place at Christmastime, complete with a fun mid-century office holiday party.9

The Bishop’s Wife (1947)

Starring Cary Grant, Loretta Young, and David Niven, “The Bishop’s Wife” is a romantic fantasy. It tells the story of a bishop who prays for guidance and receives help from a charismatic angel. The film explores themes of love, morality, and the true meaning of Christmas. This blend of spiritual and romantic themes creates a heartwarming narrative that resonates deeply during the holiday season. It’s an enchanting and uplifting movie, perfect for those seeking a mix of romance and holiday spirit.10

The Shop Around the Corner (1940)

“The Shop Around the Corner,” a romantic comedy starring James Stewart and Margaret Sullavan, revolves around two feuding co-workers who, unbeknownst to each other, are anonymous pen pals. If that premise sounds familiar, it may be because you’ve seen Nora Ephron’s beloved “You’ve Got Mail” (1998), a loose adaptation. The film is celebrated for its witty script and the chemistry between its leads. It charmingly captures the bliss of romantic anticipation and the joy of finding love in unexpected places during the holiday season.11

Christmas in Connecticut (1945)

“Christmas in Connecticut,” another holiday rom-com starring Barbara Stanwyck, centers around a single woman who poses as a married woman and mother for her magazine column. Even though she can’t cook and doesn’t keep house, her publisher and the public believe her to be a domestic goddess. When her publisher gets the bright idea to have her host a war hero for Christmas, romance and high jinks ensue. The movie’s mix of romance and comedy provides a delightful escape, making it a wonderful choice for the holidays.12

The Thin Man (1934)

“The Thin Man” is a winning blend of comedy, mystery, and romance. The film introduces us to a charming detective duo — Nick and Nora Charles. Played by William Powell and Myrna Loy, the couple have their Christmas turned upside down by a murder case. The murder mystery, however, is more of a convenient plot device than the real star of the show. Instead, the witty banter and stylish lifestyle of the retired detective and his socialite wife are the main attractions.13 “After the Thin Man” (1936) extends the festive cheer with a case set on New Year’s Eve.14

The Curse of the Cat People (1944)

“The Curse of the Cat People” is an unconventional choice for the holidays. While it might sound like a horror film, it’s actually a magical and hauntingly beautiful ghost story about a young girl’s vivid imagination. The film explores themes of loneliness, friendship, and the power of belief. It’s a poignant and visually striking film that offers a different kind of Christmas magic. “The Curse of the Cat People” is technically a sequel to “Cat People” (1942), but it isn’t dependent on that story and it has a completely different vibe.15

In the Good Old Summertime (1949)

Despite its title, “In the Good Old Summertime” (1949) is a seasonally appropriate choice for Christmas. Starring Judy Garland and Van Johnson, this movie musical is a loose adaptation of “The Shop Around the Corner.” It’s filled with delightful musical numbers and charming performances. The film’s warmth and cheer make it a fitting addition to any holiday movie lineup.16 For another musical adaptation of the core story, there’s the also Christmassy Broadway musical “She Loves Me.” The 2016 revival was filmed and is available to stream.17

Bachelor Mother (1939)

“Bachelor Mother” is a holiday rom-com starring Ginger Rogers and David Niven. It tells the story of a single salesgirl who is mistakenly believed to be the mother of an abandoned baby. Rogers’ portrayal of a salesgirl caught in a comedic mix-up is sweet and entertaining. It provides an amusing yet heartwarming take on holiday miracles.18 Fans of this film might also enjoy “Bundle of Joy” (1956), a movie musical adaptation starring Debbie Reynolds, which offers a similar blend of humor and holiday spirit.19

The Enduring Magic of Classic Christmas Movies

These classic holiday films offer a range of stories that capture the spirit of the season. Together, they illustrate the diverse ways in which the holiday season has been celebrated in cinema over the years. As we immerse ourselves in these classic Christmas tales, we’re reminded of the joy and magic that the holiday season brings.

Katie Ormsby



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