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Written by Timothy Sexton
In a manic portrayal by Jack Lemmon, bull fiddle player Jery transforms into Daphne and genuinely creates what at times seems like a completely different—and quite female—character. Daphne allows Jerry to loosen up and tap into his playful side and Lemmon plumbs that dichotomy to an Oscar nomination for Best Actor and what should have rightfully been an Oscar win.
Joe/Josephine/Shell Oil Junior
Joe is Jerry’s best friend, a tenor sax player who uses his considerable charm to manipulate women and Jerry into doing whatever he wants. Josephine is Joe’s alter ego when they two join an all-girl band in a desperate attempt to escape from the long arm of the Chicago mob after they become the only two living witnesses to the St. Valentine’s Day Massacre not actually associated with the crime. In his attempt to make Sugar Kane another of his many sexual conquests, Joe concocts yet another persona in the Cary Grant-soundalike oil tycoon.
The sexy lead singer and part-time ukulele player of the all-girl band that Jerry and Joe join undercover as Daphne and Josephine. Sugar describes herself as always getting the fuzzy end of the lollipop because she constantly falls for tenor sax players who leave her high and dry. Now she’s on the lookout for a brainy type with glasses. Tenor sax player Joe uses the inside information he gets as Josephine to set himself up as a brainy, glasses-wearing heir to an oil tycoon in an effort to win Sugar’s affections.
Osgood Fielding III
The all-girl band has been booked to play a hotel in Florida which is mainly populated by wealthy older men who have migrated south to escape the winter. One of the many older rich guys looking to find younger women looking for a sugar daddy is Osgood Fielding III who sets his leering eye upon—despite the plethora of other very attractive young females in the band—Daphne.
So named because of his natty footwear which is the first the audience sees of him when Joe and Jerry watch him get out of his car in the garage in which he gives the order for the St. Valentine’s Day Massacre to commence. In one of those wonderfully improbable coincidences that happens in real life almost as much as in the movies, Spats attends a sort of mobster convention at the very same hotel where Jerry and Joe are hiding out from Spats in disguise as Daphne and Josephine. Spats is played by George Raft who was one of the most recognizable faces from the gangster movies of the 1930s.
Detective Mulligan is hot on the trail of Spats immediately from the aftermath of the massacre and follows him down to the Florida hotel where Spats, Jerry and Joe are all headed to an inevitable confrontation between killer and witnesses. Mulligan is played by Pat O'Brien who also had an extensive career in gangster movies.
The bandleader of the all-girl band that Joe and Jerry join. The name of the band is actually Sweet Sue and Her Society Syncopators.
The traveling manager of Sweet Sue and Her Society Syncopators is known only as Mr. Beinstock because of Sweet Sue’s habit of loudly calling out “BEINSTOCK” whenever one of the girls in the band causes trouble. Such as when Sugar Kane’s flask of alcohol slips from beneath her garter and Daphne quick steps in to rescue her by taking the fall.
Bearing more than a little physical resemblance to former Italian dictator Mussolini and with a name that recalls iconic the iconic movie gangster played by Edward G. Robinson in Little Caesar, Little Bonaparte is the mob boss of bosses who has determined that Spats Colombo has got a little too big for his spats and when his masterminding the St. Valentine’s Day Massacre. Little Bonaparte is himself the mastermind behind the mobster convention at the Florida hotel where he plans to surprise Spats and his gang by hiding assassins inside the giant celebration cake instead of a stripper.
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