[Lio]

I'd go with Unforgiven (1992).

He was perfect as the sherif. One of those morally ambiguous characters, that you warm to but know is really a bad guy (much like the Clint Eastwood's lead character).

(...to be honest it's a tough call between Popeye Doyle or Royal Tenenbaum too).

[booleanbetrayal]

I second this. "Little Bill" was portrayed in such a way, that as a viewer, you are pulled between rationalizing and condemning his actions. Fantastic movie with superb acting on Hackman's (and truly, every other actor's) part.

[relistan]

Clint Eastwood is not my favorite human by a long shot, but that movie and Hackman’s performance are both amazing.