Why it's so great: Dustin Hoffman, Jessica Lange, Dabney Coleman and Bill Murray all shine in this dramedy about an actor (Hoffman) who pretends to be a woman to get roles, and finds out more about both himself and supposed gender roles than he anticipated. 

Remake-o-meter says: "Tootsie" was smart, brash and took its time developing characters and situations, resulting in big dramatic payoffs (not just big laughs). It's tough to imagine a studio remake that wouldn't just go for the easy laughs of "dude look like a lady". Today's audiences can stick with the "Big Momma's House" franchise for that.