Every summer Adam Sandler and I have a little ritual. He makes a new movie, and I get myself secretly excited that somehow, in some small way, he will be able to tap into the greatness he found in his best role, eight years ago. And each summer there are moments, small glimpses, proof that he could do it again, but he somehow refuses. His best role is an obvious choice: as Barry Egan in Paul Thomas Anderson's Punch-Drunk Love (2002), because it's the only choice. And whatever he did to get there must have been too much work, too frightening, or cost too much.
Before 2002, Adam Sandler was a cult hero to teenage males and frat boys, and hardly anyone took him seriously, except possibly as an investment on another highly successful comedy. Movie critics certainly would never have admitted to liking him. (I'm personally rather fond of Michael Lehmann's Airheads, however.) I suspect that the critically panned Happy Gilmore (1996) has become a favorite in retrospect, known primarily for Sandler's golf course fight with Bob Barker. It's an interesting movie in many ways, because it establishes Sandler's comic persona. He plays a failed hockey player who lives with his grandma. He loves her dearly, and treats her with kindness and respect, without a hint of irony. But when he gets on the golf course, he explodes, and his outrageous temper makes him do funny things. That movie wasn't clever enough to really tie together the two sides, or to do anything interesting with the plot, but it was a start.