Billy Madison (1995)

No one was bigger in the world of comedy in 1995 than Adam Sandler, and in the wacky comedy Billy Madison, he takes on the role of a schoolboy! Sandler plays the adult son of a filthy rich hotel magnate, and spends his days luxuriating and partying, much to the chagrin of his high-powered papa. When his father decides that he's had enough, he makes Billy go back to finish school in 24 weeks. That's every grade! While he may be a manchild, Sandler is all man in the Billy Madison opening credits, where he flaunts his surprisingly buff bod (complete with a perfect 90s tan!) while floating around in the pool. Throw in some shirtless action from SNL funnyman Chris Farley, and we're sold. Too bad Billy doesn't show his willy!