Nobody's Perfect (1990)

Taking its title from the legendary last line of Billy Wilder's Some Like it Hot, the cross-dressing comedy Nobody's Perfect (1990) pilfers elements of that film's plot, along with about a dozen other previous guys-dress-like-girls movies! Chad Lowe is the guy in the equation this time around, college freshman tennis player Stephen, who becomes head over heels obsessed with upperclass female tennis player Shelly (Gail O'Grady). His obsession becomes so strong that he can't eat, sleep, or even play tennis anymore, leading him to get kicked off of the team. With nothing left to lose and operating under the advice of his boneheaded pals, Stephen decides to become Stephanie and try out for the girls' tennis team! Of course, because this is an early 90s comedy, everything in this psychotic plan actually works for a little while and Stephen is able to get close to Shelly, even though he's pretending to be Stephanie. The one thing this film does presage in terms of cross-dressing psycho comedies is that Stephen's ruse is exposed in the same manner that Daniel Hillard's is exposed in Mrs. Doubtfire, released three full years after this film... conspiracy time! Since this is a cross-dressing PG-13 1990s comedy, expect a gratuitous locker room scene with at least one topless extra who remains uncredited. Gail O'Grady leaves her bra on in the locker room scene, but any chance to peep those magnificent melons is one worth taking! Nobody's Perfect, but Gail's rack comes damn close!