Starred in: Swingers ('96); Iron Man I ('08) and II ('10)
Directed: Elf (2003); Zathura ('05); Iron Man I and II ; Cowboys & Aliens ('11)
Jon got his acting start through small walk-on roles (including an easily-missed bit as the culturally ignorant Eric the Clown in Seinfeld) but earned his fame opposite Vince Vaughn in the influential indie movie, Swingers. Today we know and love him for his work behind the camera, and as Tony Stark's charmingly benign bodyguard/bro Happy Hogan, in the new Iron Man franchise. He also did about as much as anyone could've with the messy, nine-authored script for Cowboys & Aliens last year. Knowing there's a third Iron Man hot on its way, we'll give Jon a pass on that.