Mob Queen (1998)

"If it's your boss's birthday, you'd better get him a present"

In Brooklyn of the '50s, small-time mobster George and his sidekick Dip realize they've forgotten the birthday of mob boss Joey, so they engage the services of prostitute Glorice. Joey's reaction to Glorice gives George a promotion, and he's installed as Joey's assistant. George makes the discovery that gender-bent Glorice is not exactly a woman after all. The problem gets worse: Joey intends to marry Glorice, who plans to blackmail Joey after the wedding.