If things had worked out a little differently, Paul Rudd might have become a huge star in the 1990s -- but instead, his breakout performance in Clueless led to a brief appearance in Baz Luhrmann's Romeo + Juliet and big parts in a couple of forgettable romantic comedies. The decade of supporting roles that followed may not have filled Rudd's bank account with leading man money, but they added up to an eclectic filmography -- and by the time he broke out all over again as a member of Team Apatow, he was one of the more recognizable faces in the industry.