Judging on how quickly JumpinJesus did that one, I suspect that none of these will be impossible.
Alright, James Stewart. JS was in It's a Rear Window, which was directed by Alfred Hitchcock. Hitchcokcs last work, Family Plot, featured William Devane. William Devane was in Hollow Man with Kevin Bacon (didn't this game used to be called six degrees of Kevin Bacon? Of well). Bacon was in Beauty Shop with Queen Latifa, who was in Taxi (the American remake) with Jimmy Fallon. Jimmy was on SNL with Rob Schneider. Schneider was in Eight Crazy Nights with Tyra Banks (she was a voice talent). Tyra was in Coyote Ugly with John Goodman, who was in King Ralph with Peter O'Tool. P dog was in Troy with Orlando Bloom. But TLOTR is too easy, so Orlando was in Kingdom of Heaven with Liam Neeson...who was Oskar Schindler in Schindler's List.
Next person or movie to connect:
Konstantin Khabensky of NightWatch fame.