Stuntman
Dick Warlock (Spider-Man) -> Willem Dafoe (xXx: State of the Union) -> Samuel L. Jackson.
Actor
Dick Warlock (The Abyss) -> Mary Elizabeth Mastrantonio (The Perfect Storm) -> George Clooney (Ocean's Eleven) -> Matt Damon (Good Will Hunting) -> Ben Affleck (Jay and Silent Bob Strike Back) -> Carrie Fisher and Mark Hamill
Okay, this won't be all that hard, but he was cool: Burgess Meredith.