Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen in White Christmas (1954)

Fred Astaire, Bing Crosby, Virginia Dale, and Marjorie Reynolds in Holiday Inn (1942)

Joan Blondell, Bing Crosby, and Mischa Auer in East Side of Heaven (1939)

Joan Blondell, Bing Crosby, Mischa Auer, and Baby Sandy in East Side of Heaven (1939)

Bing Crosby and Marion Davies in Going Hollywood (1933)

Bing Crosby and Bob Hope in Olympic Fund Telethon (1952)

Bing Crosby and Dorothy Lamour in Dixie (1943)

Bing Crosby, Dorothy Lamour, and Marjorie Reynolds in Dixie (1943)

Bing Crosby, Bob Burns, and Martha Raye in Waikiki Wedding (1937)

Bing Crosby, Bob Burns, Martha Raye, and Shirley Ross in Waikiki Wedding (1937)

Bing Crosby and Martha Raye in Waikiki Wedding (1937)

Milton Berle, Bing Crosby, Bob Hope, and Danny Kaye in The Sound of Laughter (1963)

Bing Crosby, Dick Martin, and Dan Rowan in Rowan & Martin's Laugh-In (1967)

Bing Crosby in Rowan & Martin's Laugh-In (1967)

Bing Crosby and Betty Hutton in Here Come the Waves (1944)

Bing Crosby in Here Come the Waves (1944)

William Bendix, Bing Crosby, and Cedric Hardwicke in A Connecticut Yankee in King Arthur's Court (1949)

Bing Crosby and Cedric Hardwicke in A Connecticut Yankee in King Arthur's Court (1949)

Bing Crosby, Danny Kaye, Rosemary Clooney, Vera-Ellen, Bob Wallace, and Betty Haynes in White Christmas (1954)

Bing Crosby, Danny Kaye, Michael Curtiz, Rosemary Clooney, and Vera-Ellen in White Christmas (1954)

Bing Crosby in The Bells of St. Mary's (1945)

Bing Crosby, William Gargan, and Martha Sleeper in The Bells of St. Mary's (1945)

Ingrid Bergman and Bing Crosby in The Bells of St. Mary's (1945)

Bing Crosby and Rhys Williams in The Bells of St. Mary's (1945)

Bing Crosby and Henry Travers in The Bells of St. Mary's (1945)

Grace Kelly, Frank Sinatra, and Bing Crosby in High Society (1956)

Bing Crosby and Nancy Olson in Mr. Music (1950)

William Holden, Bing Crosby, Bob Hope, Ray Milland, and Mary Hatcher in Variety Girl (1947)

Bing Crosby, Coleen Gray, and Clarence Muse in Riding High (1950)

Bing Crosby and Paul Whiteman in King of Jazz (1930)

Jack Benny, Bing Crosby, and Bob Hope in The Jack Benny Program (1950)