1
White Christmas (1954)
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Director Michael Curtiz
Writer Norman Krasna, Norman Panama, Melvin Frank
Cast Bing Crosby, Danny Kaye, Rosemary Clooney
Plot A successful song-and-dance team become romantically involved with a sister act and team up to save the failing Vermont inn of their former commanding general.
2
Holiday Inn (1942)
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Director Mark Sandrich, Robert Allen
Writer Claude Binyon, Elmer Rice, Irving Berlin
Cast Bing Crosby, Fred Astaire, Marjorie Reynolds
Plot At an inn which is open only on holidays, a crooner and a hoofer vie for the affections of a beautiful up-and-coming performer.
3
Going My Way (1944)
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Director Leo McCarey
Writer Frank Butler, Frank Cavett, Leo McCarey
Cast Bing Crosby, Barry Fitzgerald, Frank McHugh
Plot When young Father O'Malley arrives at St. Dominic's, old Father Fitzgibbon doesn't think much of his new assistant.
4
The Adventures of Ichabod and Mr. Toad (1949)
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Director James Algar, Clyde Geronimi, Jack Kinney
Writer Washington Irving, Kenneth Grahame, Erdman Penner
Cast Bing Crosby, Basil Rathbone, Eric Blore
Plot An animated adaptation of "The Wind in the Willows" followed by an adaptation of "The Legend of Sleepy Hollow".
5
The Bells of St. Mary's (1945)
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Director Leo McCarey
Writer Dudley Nichols, Leo McCarey, Louis Sauvat
Cast Bing Crosby, Ingrid Bergman, Henry Travers
Plot At a big city Catholic school, Father O'Malley and Sister Benedict indulge in friendly rivalry, and succeed in extending the school through the gift of a building.
6
High Society (1956)
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Director Charles Walters
Writer John Patrick, Philip Barry
Cast Bing Crosby, Grace Kelly, Frank Sinatra
Plot With socialite Tracy Lord about to remarry, her ex-husband - with the help of a sympathetic reporter - has 48 hours to convince her that she really still loves him.
7
The Legend of Sleepy Hollow (1949)
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Director Clyde Geronimi, Jack Kinney
Writer Erdman Penner, Joe Rinaldi, Winston Hibler
Cast Bing Crosby, Billy Bletcher, Pinto Colvig
Plot In a small town, a brewing romantic rivalry with a local tough and a school-teacher culminates in a terrifying ride in the night.
8
Road to Morocco (1942)
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Director David Butler
Writer Frank Butler, Don Hartman, Erik Charell
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Two carefree castaways on a desert shore find an Arabian Nights city, where they compete for the luscious Princess Shalmar.
9
The Country Girl (1954)
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Director George Seaton
Writer Clifford Odets, George Seaton
Cast Bing Crosby, Grace Kelly, William Holden
Plot A director hires an alcoholic has-been and strikes up a stormy relationship with the actor's wife, who he believes is the cause of all the man's problems.
10
Road to Utopia (1945)
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Director Hal Walker
Writer Norman Panama, Melvin Frank
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Two vaudeville flops pose as bad guys and join the Klondike gold rush with a saloon singer.
11
Road to Rio (1947)
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Director Norman Z. McLeod
Writer Edmund Beloin, Jack Rose, Barney Dean
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Two inept vaudevillians stow away on a Brazilian-bound ocean liner and foil a plot by a sinister hypnotist to marry off her niece to a greedy fortune hunter.
12
That's Entertainment! (1974)
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Director Jack Haley Jr.
Writer Jack Haley Jr.
Cast Fred Astaire, Gene Kelly, Bing Crosby
Plot Various MGM stars from yesteryear present their favorite musical moments from the studio's 50-year history.
13
Road to Singapore (1940)
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Director Victor Schertzinger
Writer Don Hartman, Frank Butler, Harry Hervey
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Two playboys try to forget previous romances in Singapore - until they meet a beautiful dancer.
14
Road to Zanzibar (1941)
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Director Victor Schertzinger
Writer Frank Butler, Don Hartman, Sy Bartlett
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Stranded in Africa, Chuck and his pal Fearless have comic versions of jungle adventures, featuring two attractive con women.
15
Road to Bali (1952)
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Director Hal Walker
Writer Frank Butler, Hal Kanter, William Morrow
Cast Bing Crosby, Bob Hope, Dorothy Lamour
Plot Two unemployed show-biz pals accept treasure-diving work in Bali for a local princess and they find treasure, love and trouble.
16
A Connecticut Yankee in King Arthur's Court (1949)
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Director Tay Garnett
Writer Edmund Beloin, Mark Twain
Cast Bing Crosby, Rhonda Fleming, Cedric Hardwicke
Plot A singing mechanic from 1912 finds himself in Arthurian Britain.
17
The Road to Hong Kong (1962)
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Director Norman Panama
Writer Norman Panama, Melvin Frank
Cast Bing Crosby, Bob Hope, Joan Collins
Plot Mistaken identity and the acquisition of a rare Tibetan herb put two buffoonish con men on the wrong side of a secret organization geared toward world domination.
18
Blue Skies (1946)
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Director Stuart Heisler, Mark Sandrich
Writer Arthur Sheekman, Allan Scott, Irving Berlin
Cast Fred Astaire, Bing Crosby, Joan Caulfield
Plot An ex-dancer and New York radio star narrates his love story for a band singer who loved a self-centered man who was unable to commit to his nightclub business or his family.
