Smartest Girl in Town (1936) is one of five movies of the mid-1930s in which Ann Sothern and Gene Raymond are romantic partners; the others are Hooray for Love (1935), Walking on Air (1936), There Goes My Girl (1937) and She's Got Everything (1937). Three decades later, both were cast in the political drama The Best Man (1964). According to film historian David Shipman, the pair didn't get along at all and actively disliked working together. Raymond wrote the song "Will You?" for The Smartest Girl in Town and sings it in the film to Sothern whose answer, by the way, is "No." In another tart dialogue exchange, Raymond asks if he may smoke and Sothern snaps, "Go ahead, if you think you're so hot."
A character refers to the Gene Raymond character as a "bohunk." This was a disparaging term for the chunky, blond, blue-eyed immigrants from Bohemia (Raymond was actually born in New York City and was of French ancestry).
Richard sings "Will You?" to Francis (Ann Sothern) during their whirlwind courtship. Gene Raymond actually wrote this song. This song was also performed the next year in the Barbara Stanwyck screwball comedy Breakfast for Two (1937).
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