Shadow of the Vampire (2000)
What if the actor in Nosferatu was a real vampire? The conceit is irresistible.
Cary Elwes played Westley in The Princess Bride and trained for months in fencing so that the duel with Mandy Patinkin could be shot in long takes with no doubles, which is why it remains the best sword fight in American film.
Robin Hood: Men in Tights then parodied the same persona, and he has moved between the two registers since.
Glory, Twister and Saw filled out a varied career, and the Saw performance is generally considered the weakest thing in a very successful film.
He wrote a memoir about The Princess Bride that is unusually generous about everyone involved.