Johnny Suede (1991)

Tom DiCillo's weirdo black comedy Johnny Suede (1992) stars Bratt Pitt as the titular character, a pompadoured pretty boy with a dream as big as his hair—to be a rock star just like Ricky Nelson himself. All he needs is a pair of black suede shoes, which magically appear and make his life all but complete. But is any life complete without a pair of sweater meats and a sweet, sweet seat? Of course not! That's where Alison Moir comes in (though come out of her clothes she does not in this one—you'll have to turn to Exit to Eden [1994] to see more of Moir). Even though Ali has a heat-packing man with a busted brainpan, Brad starts seeing her on the regular. Things are looking good until he has to pawn his guitar, losing Ali in the process. Feeling low, Brad wanders aimlessly until comely Catherine Keener shows up to teach him that his life is already peachy keen.