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The Best Bing Crosby Movies

Updated May 20, 2020 3.3k votes 519 voters 39.9k 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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  • 1
    White Christmas
    164
    32

    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 on Wikipedia

    More White Christmas 

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  • 2
    The Country Girl
    124
    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 on WikipediaAmazon_watch buy button
  • 3
    Holiday Inn
    132
    23

    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 on Wikipedia

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    #1022 of 1,189 Every Oscar Winning Film Ever#1509 of 1,647 The Most Rewatchable Movies

  • 4
    Going My Way
    129
    22

    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 on WikipediaAmazon_watch buy button

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    #107 of 356 The Best Musical Movies Of All Time#79 of 92 The Very Best Oscar-Winning Movies For Best Picture

  • 5
    The Bells of St. Mary's
    122
    18

    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 on Wikipedia

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  • 6
    High Society
    89
    17

    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 on Wikipedia
  • 7
    Pennies from Heaven
    67
    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 on Wikipedia
  • 8
    Road to Morocco
    56
    10

    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 on WikipediaAmazon_watch buy button

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    #262 of 922 The All-Time Greatest Comedy Films#455 of 1,137 The Absolute Funniest Movies Of All Time

  • 9
    A Connecticut Yankee in King Arthur's Court
    54
    15

    Released1949

    Directed byTay Garnett

    A Connecticut Yankee in King Arthur's Court is a 1949 American musical comedy film directed by... more on WikipediaAmazon_watch buy button
  • 10
    The Big Broadcast
    37
    5

    The Big Broadcast

    Bing Crosby, George Burns

    Released1932

    Directed byFrank Tuttle

    The Big Broadcast is a 1932 American musical comedy film directed by Frank Tuttle and starring... more on WikipediaAmazon_watch buy button
  • 11
    College Humor
    38
    7

    College Humor

    Bing Crosby, George Burns

    Released1933

    Directed byWesley Ruggles

    College Humor is a 1933 American musical comedy film directed by Wesley Ruggles and starring... more on WikipediaAmazon_watch buy button
  • 12
    Blue Skies
    42
    13

    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 on WikipediaAmazon_watch buy button
  • 13
    Road to Bali
    40
    13

    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 on Wikipedia

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  • 14
    Road to Utopia
    31
    9

    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 on WikipediaAmazon_watch buy button
  • 15
    Robin and the Seven Hoods
    38
    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 on Wikipedia
  • 16
    The Adventures of Ichabod and Mr. Toad
    35
    14

    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 on Wikipedia

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  • 17
    Here Comes the Groom
    42
    25

    Here Comes the Groom

    Bing Crosby, Jane Wyman

    Released1951

    Directed byElliott Nugent, Frank Capra

    Here Comes the Groom is a 1951 musical romantic comedy film produced and directed by Frank... more on Wikipedia
  • 18
    Welcome Stranger
    29
    10

    Welcome Stranger

    Bing Crosby

    Released1947

    Directed byElliott Nugent

    Welcome Stranger is a 1947 comedy film directed by Elliott Nugent.Amazon_watch buy button
  • 19
    We're Not Dressing
    38
    21

    We're Not Dressing

    Bing Crosby, Carole Lombard

    Released1934

    Directed byNorman Taurog

    We're Not Dressing is a 1934 screwball musical comedy directed by Norman Taurog. Based on the... more on WikipediaAmazon_watch buy button
  • 20
    Road to Singapore
    29
    11

    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 on WikipediaAmazon_watch buy button
  • 21
    Here come the Waves
    33
    15

    Here come the Waves

    Bing Crosby, Betty Hutton

    Released1944

    Directed byMark Sandrich

    Here come the Waves is a 1944 musical comedy film directed by Mark Sandrich.Amazon_watch buy button
  • 22
    Hollywood Victory Caravan
    26
    9

    Hollywood Victory Caravan

    Humphrey Bogart, Bob Hope

    Released1945

    Directed byWilliam D. Russell

    The Hollywood Victory Caravan was a three-week railroad journey of 1942 that brought a number... more on WikipediaAmazon_watch buy button
  • 23
    Hollywood Party
    40
    25

    Hollywood Party

    Lucille Ball, Mickey Rooney

    Released1934

    Directed byRoy Rowland

    Hollywood Party is a musical film starring Jimmy Durante and distributed by... more on WikipediaAmazon_watch buy button
  • 24
    Riding High
    37
    23

    Riding High

    Bing Crosby, Margaret Hamilton

    Released1950

    Directed byFrank Capra

    Riding High is a black and white musical racetrack film featuring Bing Crosby and directed by... more on WikipediaAmazon_watch buy button
  • 25
    Rhythm on the Range
    29
    14

    Rhythm on the Range

    Bing Crosby, Bob Burns

    Released1936

    Directed byNorman Taurog

    Rhythm on the Range is a 1936 American Western musical film directed by Norman Taurog and... more on WikipediaAmazon_watch buy button