Bing Crosby got his start in show business alongside partner Al Rinker in Paul Whiteman's orchestra, touring across the United States. Before long, Crosby's popularity was rising fast, and by 1931 the crooner decided to strike out on his own as a solo artist. After starring in musical shorts produced by Mack Sennett, Crosby was offered a contract with Paramount Pictures. Bing Crosby was everywhere, from radio to records to feature-length films, and by the late 1930s he had established himself as one of the most popular entertainers in the world. Immediately following the success of 1936's Pennies from Heaven, also starring Madge Evans, Edith Fellows and Louis Armstrong, Crosby was cast in another musical for Paramount-- Waikiki Wedding (1937), directed by Frank Tuttle and featuring Bob Burns, Martha Raye and Shirley Ross.

Crosby is ad-man Tony Marvin, working for J.P. Todhunter's Imperial Pineapples, located in the Hawaiian Islands. To boost sales and promote tourism to the islands, Tony concocts a marketing campaign to search for an "Imperial Pineapple Girl," a spokesmodel of sorts for the company. Once chosen by way of contest, the Imperial Pineapple Girl will spend a few weeks in Hawaii soaking up the sun and finding romance, while her exploits--all arranged by the company--are written up by Tony and published for consumers to read. After selecting the beautiful Georgia Smith (played by Shirley Ross) as their girl, it soon becomes clear that their advertising scheme isn't going to work as planned, and Tony and his boss, Mr. Todhunter, devise a plan to keep Georgia on the island so their campaign doesn't go bust.

Waikiki Wedding was Paramount's answer to the popular musicals produced by rival studio RKO starring Fred Astaire and Ginger Rogers and star-studded affairs released by MGM. While this film wasn't nearly as successful as those musicals, it did feature great comedic performances from the supporting cast, in particular Martha Raye and Bob Burns, who make a habit of scene-stealing throughout the film.

The Montana-born Martha Raye had been under contract with Paramount Studios since 1936, with her feature-length debut being the 1936 film Rhythm on the Range also starring fellow Paramount star Bing Crosby. Raye became a comedic staple for the studio, in part because of her distinctive facial features, particularly her prominent mouth which earned her the nickname "The Big Mouth." Raye also starred in several famous radio programs, such as Al Jolson's program for CBS, as well as on the Broadway stage. Aside from her work as an entertainer, Raye also worked extensively for the USO during World War II and later as a volunteer nurse during Vietnam.

For star Bing Crosby, initially he was uninterested in Waikiki Wedding and declined the role. But after the studio reworked the script to better suit their star, Crosby accepted the part. Following Waikiki Wedding, Crosby's popularity continued to rise, hitting its peak in the 1940s and 1950s with an on-screen partnership with his good friend Bob Hope in the famous Road to movies, such as Road to Singapore (1940), Road to Morocco (1942) and Road to Rio (1947). Crosby's career took a serious turn when he won the Academy Award for Best Actor for his performance as Father Chuck O'Malley in Leo McCarey's Going My Way in 1944. Crosby reprised the role in McCarey's spiritual sequel a year later in 1945's The Bells of St. Mary's, also starring Ingrid Bergman. While Crosby explored more dramatic roles during this time, he still returned to comedies and musicals often, starring in two of his most popular films: Mark Sandrich's Holiday Inn in 1942 and White Christmas in 1954 and directed by Michael Curtiz.

The majority of the production on Waikiki Wedding was at Paramount Studios in Los Angeles, with second unit photography led by Robert Bruce taking place on-location in Hawaii to be edited into the film post-production.

Waikiki Wedding features impressive original music sung by the film's cast, including Blue Hawaii, Okolehao and Sweet Is the World for You, written by Leo Robin and Ralph Rainger; and the famous Sweet Leilani, which earned an Academy Award for Best Original Song for Harry Owens, who wrote both the music and lyrics.

Director: Frank Tuttle
Producer: Arthur Hornblow, Jr.
Screenplay: Frank Butler, Don Hartman, Walter DeLeon, Francis Martin
Cinematography: Karl Struss
Editing: Paul Weatherwax

Art Direction: Hans Dreier and Robert Usher Music: Leo Shuken
Costume Design: Edith Head
Cast: Bing Crosby (Tony Marvin), Bob Burns (Shad Buggle), Martha Raye (Myrtle Finch), Shirley Ross (Georgia Smith), George Barbier (J.P. Todhunter), Leif Erickson (Dr. Victor Quimby), and Anthony Quinn (Kimo)
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Sources:

AFI.com

By Jill Blake