In Waikiki Wedding, The Imperial Pineapple Company hires Bing Crosby, a layabout former Navy man, to come up with marketing ideas. His latest idea is to have a contest on the mainland and crown the winner "The Pineapple Girl" and award her with an all expense paid vacation to Hawaii. In exchange, she would publish her experiences in the newspaper.
The plan backfires when the Pineapple Girl finds she doesn't like Hawaii and threatens to publish this fact. It's up to Bing to show her a good time to ensure she publishes a positive review. A moonlight boat ride while crooning the Oscar winning song, Sweet Leilani, just might do the trick.
THEN
In 1937, Hawaii was a strategic American military base, a popular tourist destination for wealthy Americans, and the pineapple capitol of the world.
Hawaii was not a state, but a territory. The most significant differences being that the agriculture industry was not required to pay the same tariffs as the mainland plantations, nor were they obligated to uphold the same labor laws. The sugarcane industry prospered under this situation and wielded considerable political clout. Second to sugarcane, was pineapple. Dole pineapple, which produced 75% of the world's pineapple, was clearly the model for the "Imperial Pineapple Co." in this movie.
There was an attempt in 1937 by Congress to grant statehood to Hawaii, but it failed over issues of race as Hawaii would be the only state with a non-white majority. If this attitude was prevalent at the time, it's not apparent in the movie; the Hawaiian culture is portrayed respectfully. Plenty of dialogue and song lyrics are in the native language without subtitles, and the Hawaiian roles are played by native actors (or at least non-white actors). I don't know if Bing had a hand in ensuring that the Hawaiians were depicted with dignity, but it wouldn't surprise me. He had been insistent on the casting and prominent billing of Louis Armstrong in the previous year's Pennies From Heaven, the first time a white and black actor shared top billing on a major film.
NOW
Martha Raye and Anthony Quinn are familiar faces to today's viewer, although they were relatively unknown at the time. Martha Raye's performance is particularly over-the-top, but it was uncharted territory for a female comic at the time and a possible influence on Lucille Ball. It's hard to laugh at her humorous song about binge drinking when you know how hard her life would become due to her alcohol problems later in life.
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