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The Best Bing Crosby Movies 

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Updated May 20, 2020 2.6k votes 509 voters 39.5k views 68 items

List Rules Vote 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.

Cecil B. DeMille and Blake Edwards are among those who directed Bing Crosby at one point or another during their careers in the film industry. If you're a fan of Bing Crosby, then check out our lists of the best George Burns and Bob Hope movies as well.

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1
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Bing Crosby, Danny Kaye, Rosemary Clooney

Released: 1954

Directed by: Michael Curtiz

White Christmas is a 1954 American musical romantic comedy film directed by Michael Curtiz and starring Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen, loosely based on the 1942 film ...more

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2
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Bing Crosby, Fred Astaire, Irving Berlin

Released: 1942

Directed by: Mark Sandrich

Holiday Inn is a 1942 American musical film directed by Mark Sandrich and starring Bing Crosby and Fred Astaire. With music by Irving Berlin, the film has twelve songs written expressly for the ...more
3
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Bing Crosby, Barry Fitzgerald, William Smith

Released: 1944

Directed by: Leo McCarey

Going My Way is a 1944 American musical comedy-drama film directed by Leo McCarey and starring Bing Crosby and Barry Fitzgerald. Based on a story by Leo McCarey, the film is about a new young ...more

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4
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Ingrid Bergman, Bing Crosby, Una O'Connor

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 starring Bing Crosby and Ingrid Bergman. Written by Dudley Nichols based on a story by Leo McCarey, ...more

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5
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Frank Sinatra, Grace Kelly, Bing Crosby

Released: 1956

Directed by: Charles Walters

High Society is a 1956 American musical comedy film directed by Charles Walters and starring Bing Crosby, Grace Kelly, and Frank Sinatra. The film was produced by Sol C. Siegel for ...more
6
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Bob Hope, Bing Crosby, Anthony Quinn

Released: 1942

Directed by: David Butler

Road to Morocco is a 1942 American comedy film starring Bing Crosby, Bob Hope and Dorothy Lamour, and featuring Anthony Quinn and Dona Drake. The film, which was written by Frank Butler and Don ...more

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7
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Bing Crosby, Rhonda Fleming, Cedric Hardwicke

Released: 1949

Directed by: Tay Garnett

A Connecticut Yankee in King Arthur's Court is a 1949 American musical comedy film directed by Tay Garnett and starring Bing Crosby, Rhonda Fleming, Sir Cedric Hardwicke, and William Bendix. ...more

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8
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Grace Kelly, Bing Crosby, William Holden

Released: 1954

Directed by: George Seaton

The Country Girl is a 1954 American drama film directed by George Seaton and starring Bing Crosby, Grace Kelly, and William Holden. Adapted by George Seaton from Clifford Odets' 1950 play of the ...more
9
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Bing Crosby, Fred Astaire, Joan Caulfield

Released: 1946

Directed by: Stuart Heisler, Mark Sandrich

Blue Skies is a 1946 American musical comedy film directed by Stuart Heisler and starring Bing Crosby, Fred Astaire, and Joan Caulfield. Based on a story by Irving Berlin, the film is about a ...more
10
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Bob Hope, Dean Martin, Bing Crosby

Released: 1952

Directed by: Hal Walker

Road to Bali is a 1952 American comedy film directed by Hal Walker and starring Bing Crosby, Bob Hope, and Dorothy Lamour. Released by Paramount Pictures on November 1, 1952, the film is the ...more

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11
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Bing Crosby, Basil Rathbone, J. Pat O'Malley

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 Productions and released by RKO Radio Pictures. The film consists of two segments – the first is ...more

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12
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Frank Sinatra, Dean Martin, Bing Crosby

Released: 1964

Directed by: Gordon Douglas

Robin and the 7 Hoods is a 1964 American musical film directed by Gordon Douglas and starring Frank Sinatra, Dean Martin, Sammy Davis, Jr. and Bing Crosby. The picture features Peter Falk, ...more
13
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Bob Hope, Jim Thorpe, Bing Crosby

Released: 1945

Directed by: Hal Walker

Road to Utopia is a 1946 American comedy film directed by Hal Walker and starring Bing Crosby, Bob Hope, and Dorothy Lamour. Filmed in 1943 but not released until 1946, Road to Utopia is the ...more
14
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Bob Hope, Bing Crosby, Dorothy Lamour

Released: 1947

Directed by: Norman Z. McLeod

Road to Rio is a 1947 American comedy film directed by Norman Z. McLeod and starring Bing Crosby, Bob Hope, and Dorothy Lamour. Written by Edmund Beloin and Jack Rose, the film is about two ...more
15
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Bob Hope, Bing Crosby, Anthony Quinn

Released: 1940

Directed by: Victor Schertzinger

Road to Singapore is a 1940 American comedy film directed by Victor Schertzinger and starring Bing Crosby, Bob Hope, and Dorothy Lamour. Based on a story by Harry Hervey, the film is about two ...more
16
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Bob Hope, Bing Crosby, Dorothy Lamour

Released: 1941

Directed by: Victor Schertzinger

Road to Zanzibar is a 1941 Paramount Pictures comedy film starring Bing Crosby, Bob Hope, and Dorothy Lamour, and marked the second of seven picture in the popular "Road to …" series ...more
17
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Bing Crosby, Louis Armstrong, Lionel Hampton

Released: 1936

Directed by: Norman Z. McLeod

Pennies From Heaven is a 1936 American musical comedy film directed by Norman Z. McLeod and starring Bing Crosby, Madge Evans, and Edith Fellows. Based on the novel The Peacock Feather by ...more
18
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Bing Crosby, Joe DiMaggio, Janet Leigh

Released: 1951

Directed by: Clarence Brown

Angels in the Outfield is a 1951 American comedy film produced and directed by Clarence Brown and starring Paul Douglas and Janet Leigh. Based on a story by Richard Conlin, the film is about a ...more
19
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Ann-Margret, Bing Crosby, Stefanie Powers

Released: 1966

Directed by: Gordon Douglas

Stagecoach is a 1966 American film, directed by Gordon Douglas as a remake of the John Ford classic black-and-white western Stagecoach, which won two Academy Awards and received five other ...more

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20
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Top o' the Morning Bing Crosby, Hume Cronyn, Barry Fitzgerald

Released: 1949

Directed by: David Miller

Top o' the Morning is a 1949 American romantic comedy film directed by David Miller and starring Bing Crosby, Ann Blyth, and Barry Fitzgerald. Written by Edmund Beloin and Richard L. Breen, the ...more
21
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Bing Crosby, Ethel Merman, Ida Lupino

Released: 1936

Directed by: Lewis Milestone

Anything Goes is a 1936 American musical film directed by Lewis Milestone and starring Bing Crosby, Ethel Merman, Charles Ruggles, and Ida Lupino. Based on the stage musical Anything Goes by Guy ...more
22
Mississippi is listed (or ranked) 22 on the list The Best Bing Crosby Movies
Mississippi Bing Crosby, W. C. Fields, Joan Bennett

Released: 1935

Directed by: A. Edward Sutherland

Mississippi is a 1935 musical comedy film directed by A. Edward Sutherland and starring Bing Crosby, W. C. Fields, and Joan Bennett. Written by Francis Martin and Jack Cunningham based on the ...more
23
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Bing Crosby, Claude Dauphin, Gabrielle Dorziat

Released: 1953

Directed by: George Seaton

Little Boy Lost is a 1953 American drama film directed by George Seaton and starring Bing Crosby, Claude Dauphin, and Christian Fourcade. Based on the novel Little Boy Lost by Marghanita Laski, ...more
24
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Elizabeth Taylor, Liza Minnelli, Mickey Rooney

Released: 1974

Directed by: Jack Haley, Jr.

That's Entertainment! is a 1974 compilation film released by Metro-Goldwyn-Mayer to celebrate its 50th anniversary. It was followed by two sequels and a related film called That's Dancing!. The ...more
25
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Bing Crosby, Tuesday Weld, Yvonne Craig

Released: 1960

Directed by: Blake Edwards

High Time is a 1960 American comedy film directed by Blake Edwards and starring Bing Crosby, Fabian, Tuesday Weld and Nicole Maurey. The film is told from the perspective of a middle-aged man ...more