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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 Christmas1
    161
    35

    White Christmas

    Bing Crosby, Danny Kaye

    Released1954

    Directed byMichael Curtiz

    White Christmas is a 1954 American musical romantic comedy film directed by Michael Curtiz and...  more

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  • Holiday Inn2
    127
    21

    Holiday Inn

    Bing Crosby, Fred Astaire

    Released1942

    Directed byMark Sandrich

    Holiday Inn is a 1942 American musical film directed by Mark Sandrich and starring Bing Crosby...  more
  • Going My Way3
    123
    20

    Going My Way

    Bing Crosby, Barry Fitzgerald

    Released1944

    Directed byLeo McCarey

    Going My Way is a 1944 American musical comedy-drama film directed by Leo McCarey and starring...  more
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  • High Society4
    84
    16

    High Society

    Frank Sinatra, Grace Kelly

    Released1956

    Directed byCharles Walters

    High Society is a 1956 American musical comedy film directed by Charles Walters and starring...  more
  • The Bells of St. Mary's5
    118
    47

    The Bells of St. Mary's

    Ingrid Bergman, Bing Crosby

    Released1945

    Directed byLeo McCarey

    The Bells of St. Mary's is a 1945 American drama film produced and directed by Leo McCarey and...  more

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  • Road to Morocco6
    55
    9

    Road to Morocco

    Bob Hope, Bing Crosby

    Released1942

    Directed byDavid Butler

    Road to Morocco is a 1942 American comedy film starring Bing Crosby, Bob Hope and Dorothy...  more
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  • The Country Girl7
    43
    15

    The Country Girl

    Grace Kelly, Bing Crosby

    Released1954

    Directed byGeorge Seaton

    The Country Girl is a 1954 American drama film directed by George Seaton and starring Bing...  more
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  • A Connecticut Yankee in King Arthur's Court8
    57
    41

    Released1949

    Directed byTay Garnett

    A Connecticut Yankee in King Arthur's Court is a 1949 American musical comedy film directed by...  more
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  • Let's Make Love9
    41
    22

    Let's Make Love

    Marilyn Monroe, Bing Crosby

    Released1960

    Directed byGeorge Cukor

    Let's Make Love is a 1960 musical comedy film made by 20th Century Fox in DeLuxe Color and...  more

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  • Robin and the Seven Hoods10
    35
    17

    Robin and the Seven Hoods

    Frank Sinatra, Dean Martin

    Released1964

    Directed byGordon Douglas

    Robin and the 7 Hoods is a 1964 American musical film directed by Gordon Douglas and starring...  more
  • Sing You Sinners11
    32
    16

    Sing You Sinners

    Bing Crosby, Fred MacMurray

    Released1938

    Directed byWesley Ruggles

    Sing You Sinners is a 1938 American musical comedy film directed by Wesley Ruggles and...  more
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  • Pennies from Heaven12
    23
    9

    Pennies from Heaven

    Bing Crosby, Louis Armstrong

    Released1936

    Directed byNorman Z. McLeod

    Pennies From Heaven is a 1936 American musical comedy film directed by Norman Z. McLeod and...  more
  • Anything Goes13
    19
    6

    Anything Goes

    Bing Crosby, Ethel Merman

    Released1936

    Directed byLewis Milestone

    Anything Goes is a 1936 American musical film directed by Lewis Milestone and starring Bing...  more
  • Road to Bali14
    38
    33

    Road to Bali

    Bob Hope, Dean Martin

    Released1952

    Directed byHal Walker

    Road to Bali is a 1952 American comedy film directed by Hal Walker and starring Bing Crosby,...  more
  • She Loves Me Not15
    16
    6

    She Loves Me Not

    Bing Crosby, Miriam Hopkins

    Released1934

    Directed byElliott Nugent

    She Loves Me Not is a 1934 American comedy film directed by Elliott Nugent and starring Bing...  more
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  • Blue Skies16
    38
    35

    Blue Skies

    Bing Crosby, Fred Astaire

    Released1946

    Directed byStuart Heisler, Mark Sandrich

    Blue Skies is a 1946 American musical comedy film directed by Stuart Heisler and starring Bing...  more
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  • That's Entertainment!17
    20
    13

    That's Entertainment!

    Elizabeth Taylor, Liza Minnelli

    Released1974

    Directed byJack Haley, Jr.

    That's Entertainment! is a 1974 compilation film released by Metro-Goldwyn-Mayer to celebrate...  more
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  • Road to Utopia18
    29
    24

    Road to Utopia

    Bob Hope, Jim Thorpe

    Released1945

    Directed byHal Walker

    Road to Utopia is a 1946 American comedy film directed by Hal Walker and starring Bing Crosby,...  more
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  • Road to Rio19
    26
    24

    Road to Rio

    Bob Hope, Bing Crosby

    Released1947

    Directed byNorman Z. McLeod

    Road to Rio is a 1947 American comedy film directed by Norman Z. McLeod and starring Bing...  more
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  • Angels in the Outfield20
    24
    20

    Angels in the Outfield

    Bing Crosby, Joe DiMaggio

    Released1951

    Directed byClarence Brown

    Angels in the Outfield is a 1951 American comedy film produced and directed by Clarence Brown...  more
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  • Mississippi21
    21
    17

    Mississippi

    Bing Crosby, W. C. Fields

    Released1935

    Directed byA. 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. Toad22
    34
    37

    The Adventures of Ichabod and Mr. Toad

    Bing Crosby, Basil Rathbone

    Released1949

    Directed byJames Algar, Clyde Geronimi, Jack Kinney

    The Adventures of Ichabod and Mr. Toad is a 1949 animated package film produced by Walt Disney...  more

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  • Road to Singapore23
    28
    30

    Road to Singapore

    Bob Hope, Bing Crosby

    Released1940

    Directed byVictor Schertzinger

    Road to Singapore is a 1940 American comedy film directed by Victor Schertzinger and starring...  more
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  • Top o' the Morning24
    22
    23

    Top o' the Morning

    Bing Crosby, Hume Cronyn

    Released1949

    Directed byDavid Miller

    Top o' the Morning is a 1949 American romantic comedy film directed by David Miller and...  more
  • Stagecoach25
    25
    27

    Stagecoach

    Ann-Margret, Bing Crosby

    Released1966

    Directed byGordon Douglas

    Stagecoach is a 1966 American film, directed by Gordon Douglas as a remake of the John Ford...  more

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