The Best Bing Crosby Movies

Updated May 20, 2020 2.9k votes 537 voters 40.5k views68 items

List RulesVote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Bing Crosby movies, ranked best to worst with movie trailers when available. Bing Crosby may be best known for singing holiday classics like "White Christmas" and "Little Drummer Boy," but he also has an impressive catalog of films that are perfect to watch any time of year. Bing Crosby's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Bing Crosby movies is decided by how many votes they receive, so only highly rated Bing Crosby movies will be at the top of the list. Bing Crosby has been in a lot of films, so people often debate each other over what the greatest Bing Crosby movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Bing Crosby films to end the squabble once and for all.

If you think the best Bing Crosby role isn't at the top, then upvote it so it has the chance to become number one. The greatest Bing Crosby performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

This list features films like Going My Way and The Bells of St. Mary's.

"This list answers the questions, "What are the best Bing Crosby movies?" and "What are the greatest Bing Crosby roles of all time?" If you are a fan of Crosby's musicals, you might also enjoy our list of best Danny Kaye movies and best Frank Sinatra movies.

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White Christmas
Bing Crosby, Danny Kaye
Released: 1954
Directed by: Michael Curtiz
White Christmas is a 1954 American musical romantic comedy film directed by Michael Curtiz and... more
More White Christmas
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127
21
Holiday Inn
Bing Crosby, Fred Astaire
Released: 1942
Directed by: Mark Sandrich
Holiday Inn is a 1942 American musical film directed by Mark Sandrich and starring Bing Crosby... more
3
123
20
Going My Way
Bing Crosby, Barry Fitzgerald
Released: 1944
Directed by: Leo McCarey
Going My Way is a 1944 American musical comedy-drama film directed by Leo McCarey and starring... more
More Going My Way
#79 of 92 The Very Best Oscar-Winning Movies For Best Picture#21 of 23 The Best Musical Movies Nominated for Best Picture
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84
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High Society
Frank Sinatra, Grace Kelly
Released: 1956
Directed by: Charles Walters
High Society is a 1956 American musical comedy film directed by Charles Walters and starring... more
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118
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The Bells of St. Mary's
Ingrid Bergman, Bing Crosby
Released: 1945
Directed by: Leo McCarey
The Bells of St. Mary's is a 1945 American drama film produced and directed by Leo McCarey and... more
More The Bells of St. Mary's
#970 of 1,189 Every Oscar Winning Film Ever#42 of 91 The Best Movies With Christian Themes
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Road to Morocco
Bob Hope, Bing Crosby
Released: 1942
Directed by: David Butler
Road to Morocco is a 1942 American comedy film starring Bing Crosby, Bob Hope and Dorothy... more
More Road to Morocco
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43
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The Country Girl
Grace Kelly, Bing Crosby
Released: 1954
Directed by: George Seaton
The Country Girl is a 1954 American drama film directed by George Seaton and starring Bing... more
8
57
41
A Connecticut Yankee in King Arthur's Court
Bing Crosby, Rhonda Fleming
Released: 1949
Directed by: Tay Garnett
A Connecticut Yankee in King Arthur's Court is a 1949 American musical comedy film directed by... more
9
41
22
Let's Make Love
Marilyn Monroe, Bing Crosby
Released: 1960
Directed by: George Cukor
Let's Make Love is a 1960 musical comedy film made by 20th Century Fox in DeLuxe Color and... more
More Let's Make Love
#74 of 356 The Best Musical Movies Of All Time#47 of 76 The Greatest Musical Comedies, Ranked
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Robin and the Seven Hoods
Frank Sinatra, Dean Martin
Released: 1964
Directed by: Gordon Douglas
Robin and the 7 Hoods is a 1964 American musical film directed by Gordon Douglas and starring... more
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32
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Sing You Sinners
Bing Crosby, Fred MacMurray
Released: 1938
Directed by: Wesley Ruggles
Sing You Sinners is a 1938 American musical comedy film directed by Wesley Ruggles and... more
12
23
9
Pennies from Heaven
Bing Crosby, Louis Armstrong
Released: 1936
Directed by: Norman Z. McLeod
Pennies From Heaven is a 1936 American musical comedy film directed by Norman Z. McLeod and... more
13
19
6
Anything Goes
Bing Crosby, Ethel Merman
Released: 1936
Directed by: Lewis Milestone
Anything Goes is a 1936 American musical film directed by Lewis Milestone and starring Bing... more

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38
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Road to Bali
Bob Hope, Dean Martin
Released: 1952
Directed by: Hal Walker
Road to Bali is a 1952 American comedy film directed by Hal Walker and starring Bing Crosby,... more
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16
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She Loves Me Not
Bing Crosby, Miriam Hopkins
Released: 1934
Directed by: Elliott Nugent
She Loves Me Not is a 1934 American comedy film directed by Elliott Nugent and starring Bing... more
16
38
35
Blue Skies
Bing Crosby, Fred Astaire
Released: 1946
Directed by: Stuart Heisler, Mark Sandrich
Blue Skies is a 1946 American musical comedy film directed by Stuart Heisler and starring Bing... more
17
20
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That's Entertainment!
Elizabeth Taylor, Liza Minnelli
Released: 1974
Directed by: Jack Haley, Jr.
That's Entertainment! is a 1974 compilation film released by Metro-Goldwyn-Mayer to celebrate... more
18
29
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Road to Utopia
Bob Hope, Jim Thorpe
Released: 1945
Directed by: Hal Walker
Road to Utopia is a 1946 American comedy film directed by Hal Walker and starring Bing Crosby,... more
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26
24
Road to Rio
Bob Hope, Bing Crosby
Released: 1947
Directed by: Norman Z. McLeod
Road to Rio is a 1947 American comedy film directed by Norman Z. McLeod and starring Bing... more
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24
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Angels in the Outfield
Bing Crosby, Joe DiMaggio
Released: 1951
Directed by: Clarence Brown
Angels in the Outfield is a 1951 American comedy film produced and directed by Clarence Brown... more
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21
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Mississippi
Bing Crosby, W. C. Fields
Released: 1935
Directed by: A. Edward Sutherland
Mississippi is a 1935 musical comedy film directed by A. Edward Sutherland and starring Bing... more
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The Adventures of Ichabod and Mr. Toad
Bing Crosby, Basil Rathbone
Released: 1949
Directed by: James Algar, Clyde Geronimi, Jack Kinney
The Adventures of Ichabod and Mr. Toad is a 1949 animated package film produced by Walt Disney... more
More The Adventures of Ichabod and Mr. Toad
#154 of 575 The Best Animated Films Ever#45 of 105 The Best Halloween Movies for Kids
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Road to Singapore
Bob Hope, Bing Crosby
Released: 1940
Directed by: Victor Schertzinger
Road to Singapore is a 1940 American comedy film directed by Victor Schertzinger and starring... more

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Top o' the Morning
Bing Crosby, Hume Cronyn
Released: 1949
Directed by: David Miller
Top o' the Morning is a 1949 American romantic comedy film directed by David Miller and... more
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Stagecoach
Ann-Margret, Bing Crosby
Released: 1966
Directed by: Gordon Douglas
Stagecoach is a 1966 American film, directed by Gordon Douglas as a remake of the John Ford... more
More Stagecoach
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She Loves Me Not

Mississippi

Top o' the Morning