The movie: Billy Madison (1995), Happy Gilmore (1996), The Wedding Singer (1998), The Waterboy (1998), etc.
The player(s): Adam Sandler
Sure, other grown men have taken a run at the title. But the sum total of Adam Sandler's man child efforts—as a would-be heir forced to repeat grade school in Billy Madison, a golf pro who gets his ass kicked by Bob Barker in Happy Gilmore, a jilted groom taking out his depressive tendencies in the form of song in The Wedding Singer and a simpleton with serious football tackling abilities in The Waterboy—cannot be touched. Neither can his box office totals.