Job-averse goofball Billy Madison (Adam Sandler) stands to inherit a fortune when his hotel magnate father retires and leaves him in charge. But Billy's dad won't trust him with the family business unless he goes back to school. All the way back. While Billy's busy making good grades -- and trying to make it with his teacher (Bridgette Wilson) -- weaselly hotel executive Eric Gordon (Bradley Whitford) is waiting in the wings.