Jack Black plays Dan Landsman, a misfit who never left his suburban Pittsburgh neighborhood and has ended up chairing his high school class's 20th anniversary reunion committee, a task he's dedicated to in order to show the class that ignored him that he amounts to something. He's making very little headway drumming up interest in potential attendees, and things look pretty bleak as far as turnout. A light bulb burns brightly overhead when Dan sees a commercial on TV starring a familiar face, Oliver Lawless (Marsden), perhaps the most popular guy in his class. If he can get Oliver to come to the reunion, surely that will sway others to come too, and even better, he can tell the rest of them how he is buddies with that popular guy who has made good on his dreams to be a big-time Hollywood actor.Â