"White Christmas" is without a doubt one of the most iconic Christmas songs of all time. And that's mostly thanks to beloved actor Bing Crosby. It's no surprise that the baritone crooner released multiple Christmas albums over the years including Christmas Music, Merry Christmas, Christmas Greetings, A Christmas Sing with Bing around the World, and more.
He covers all the classics too -- "Jingle Bells," "Silent Night," "I'll Be Home For Christmas," "It's Beginning to look a lot like Christmas," "Hawaiian Christmas Song (Mele Kalikimaka)," "Santa Claus Is Comin' to Town" (w/ The Andrews Sisters), "God Rest Ye Merry Gentlemen," "Peace on Earth/Little Drummer Boy" (w/ David Bowie), "Silver Bells" (w/ Carol Richards), "Christmas in Killarney," "Winter Wonderland," "I Wish You a Merry Christmas," "Rudolph the Red-Nosed Reindeer."
That's pretty much every Christmas song ever written and that's because Bing Crosby's voice is one of the most iconic you can turn on during the holiday season. This could be because he's synonymous with some of the most beloved seasonal films ever made.
In honor of ol' Bing and the upcoming Christmas season, we have ranked all of his best holiday films.
4. Holiday Inn
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 for the real-life hotel franchise.
3. The Bells of St. Mary's
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. 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. I dare you to not cry as you watch this sweet story unfold.
2. White Christmas
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 I can remember.
1. Going My Way
The best Bing Crosby Christmas movie is without a doubt the film that earned Crosby 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 opposite Barry Fitzgerald as Father Fitzgibbon. There's lots of emotion, Christmas Eve night, a dramatic family reunion, and everything you could ever want in a feel-good film.