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The launching pad for Billy Wilder's comedy classic was a rusty old German farce, Fanfares of Love, whose two main characters were male musicians so desperate to get a job that they disguise themselves as women and play with an all-girl band in gangster-dominated 1929 Chicago. In this version, musicians Joe (Tony Curtis) and Jerry (Jack Lemmon) lose their jobs when a speakeasy owned by mob boss Spats Columbo (George Raft) is raided by prohibition agent Mulligan (Pat O'Brien). Several weeks later, on February 14th, Joe and Jerry get a job perfroming in Urbana and end up witnessing a gangland massacre in a parking garage. Fearing that they will be next on the mobsters' hit lists, Joe devises an ingenious plan for disguising their identities. Soon they are all dolled up and performing as Josephine and Daphne in Sweet Sue's all-girl orchestra. En route to Florida by train with Sweet Sue's band, the boys (girls?) make the acquaintance of Sue's lead singer Sugar Kane (Marilyn Monroe, in what may be her best performance). Joe and Jerry immediately fall in love, though of course their new feminine identities prevent them from acting on their desires. Still, they are determined to woo her, and they enact an elaborate series of gender-bending ruses complicated by the fact that flirtatious millionaire Osgood Fielding (Joe E. Brown) has fallen in love with "Daphne." The plot gets even thicker when Spats Columbo and his boys show up in Florida. Nominated for several Oscars, Some Like It Hot ended up the biggest moneymaking comedy up to 1959. Full of hilarious set pieces and movie in-jokes, it has not tarnished with time and in fact seems to get better with each passing year, as its cross-dressing humor keeps it only more and more up-to-date. ~ Hal Erickson, Rovi

Michael Dorsey (Dustin Hoffman), a brilliant but troublesome New York actor, has managed to alienate every producer on both coasts. Michael's agent George Fields (Sydney Pollack) can't even get his client a commercial since Michael complained that the tomato he was playing wasn't properly motivated. "You were a tomato!" screams George in desperation, adding that Michael is so obnoxious that he will probably never work again. Dorsey thinks otherwise; when he hears of an opening on a popular soap opera, he applies for the job--even though the job is for a woman. Posing as "Miss Dorothy Michaels," Michael wins the part and becomes a widely-known actress. Yet complications ensue when Michael falls for his co-star Julie (Jessica Lange, in an Oscar-winning performance) but, as Dorothy, is courted by Julie's widowed father (Charles Durning). Michael ultimately finds that his disguise as a woman has made him a better man. One of the classic comedies of the 1980s, Tootsie's gender-bending premise boasts a screenplay by Larry Gelbart and Murray Schisgal, and by a host of memorable supporting comic performances from Dabney Coleman, Teri Garr, George Gaynes, and Bill Murray. Future Oscar-winner Geena Davis makes her screen debut as a daytime drama queen, which indeed she had been before Tootsie came along. ~ Hal Erickson, Rovi