"White Christmas" is, without a doubt, one of the best Christmas songs of all time. While there have been countless iconic covers of the holiday classic, that's mostly thanks to beloved actor and singer Bing Crosby, who was first to bring it to the big screen. Crosby has become synonymous with the holiday season over the years, in part due to his many recordings of classic Christmas songs ranging from "Little Drummer Boy" to "Rudolph the Red-Nosed Reindeer." but also due to his roles in a few memorable holiday films. Bing Crosby Christmas movies are just required viewing once the holiday season hits.
Crosby starred in a total of four classic Christmas movies, and every single one regularly appears on lists of the best of all time. Not only do we get to hear his lovely baritone voice in every single one, but each follows a truly touching holiday story that stands the test of time. From a priest helping his parish in an impoverished community (twice) to a singer helping to bring some Christmas cheer to his former WWII commander, these are all Christmas classics for a reason that everyone should see at least once in their lifetime.
In honor of ol' Bing and the upcoming Christmas season, we have ranked all of his best holiday films.
4. 'Holiday Inn' (1942)
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This classic Christmas film stars Bing Crosby opposite Fred Astaire, Marjorie Reynolds, Virginia Dale, and Walter Abel. It's also best known for being the film that gave us the song "White Christmas," which earned composer Irving Berlin an Oscar for Best Original Song in 1941. Bing sings "White Christmas" in the film like the holiday angel he is and helped turn it into the iconic song it is today.
The film centers around Jim Hardy (Crosby), Ted Hanover (Astaire), Linda Mason (Reynolds), and Danny Reed (Abel). There's a love triangle, a Holiday Inn, and lots of incredible singing in this musical film. Fun fact, the film also inspired the name of the real-life hotel franchise.
Where to watch: Rent on YouTube, rent on AppleTV
3. 'The Bells of St. Mary's' (1945)
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In the sequel to "Going My Way," Crosby returns to play the role of Father Chuck O'Malley, which earned him a nomination for the Academy Award for Best Actor. He actually became the first actor to ever receive an Oscar nomination twice for playing the same character. Father Chuck is assigned to the run-down St. Mary's parish, which includes an old inner-city school. Ingrid Bergman co-stars as Sister Mary Benedict. The two work together to save the school in this emotional holiday film.
Where to watch: PlutoTV, Tubi, Sling TV, the Roku Channel
2. 'White Christmas' (1954)
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This really is the Christmas song of all classic Christmas songs. Outside of maybe Judy Garland singing "Have Yourself a Merry Little Christmas" in "Meet Me In St. Louis," this is what most people think of when a classic holiday song comes to mind. Not to mention the compilation of music in this film between Crosby, Danny Kay and Rosemary Clooney, and the many duets — it's holiday gold. The story in this film will definitely have you crying the first time (every time) you watch it. It's been a holiday staple in my house for as long as we can remember.
Where to watch: Netflix, rent on Prime Video
1. 'Going My Way' (1944)
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The best Bing Crosby Christmas movie is, without a doubt, the film that earned him an Oscar, "Going My Way." The film won a whopping 7 Oscars of 10 nominations, including winning Best Picture. It followed the story of Father Chuck O'Malley (Crosby) opposite Barry Fitzgerald as the older and skeptical Father Fitzgibbon. Father O'Malley inspires his tough neighborhood parish by forming a boys choir. Though not technically a formal 'Christmas movie,' this film has always been closely associated with the season. There's lots of emotion, Christmas Eve night, a dramatic family reunion, and everything you could ever want in a feel-good film.
Where to watch: Prime Video
