Well, with this fantastic discussion, you guys have inspired me to start the
William Atherton Appreciation Thread that I have wanted to make fo some time, but I've just been too lazy to.
Great call on Fred McMurray in The Apartment.
My next list of nominees:
I don't know if he counts, because his character avolution is fairly positive and schmaltzy, but Jack Nicholson as Melvin Udall in As Good as it Gets is an incredibly large asshole, especially for the lead character in a modern film. But again, he goes all pussy on us all and begins to evolve.
Robert Shaw as Doyle Lonnegan in The Sting. It was a harmless grift, Lonnegan, why do you have to go and kill Luther up like you do? Accept the loss on move on! But no, you're far too big of an asshole. You deserve what's coming to ya, Lonnegan, and I don't know anyone who isn't completely pleased when it happens.
Zero Mostel's Max Bialystock from the original The Producers. He dupes old women into giving him money. He manipulates a mousy accountant into a criminal. HE PRODUCES A PLAY ABOUT HITLER. What an asshole.
Sam Rockwell as Frank Mercer in Matchstick Men. (SPOILERS FOLLOW) He gains Nic Cage's trust and becomes his only friend. He uses all of that information to send in his girlfriend to act like Cage's daughter. Who cares what emotional investment Cage may have in it all - he wants the money! And then he has the gall to come in with Alison Lohman and screw up the last ten minutes of the movie. Come on!
Jason Isaac's Captain Hook in P.J. Hogan's Peter Pan. Captain Hook is an asshole, but Jason Isaac's Captain Hook is the definitive version of that asshole. He's obsessed with killing a boy. A young boy. That is pretty much his driving force and main goal in life: kill a child. To accomplish this goal, he'll do anything. Isaac's Hook has no problem shooting his men for no other reason than they said something stupid. Plus, he makes a preteen girl walk the plank. WTF?
Richard Roxbourgh as The Duke in Moulin Rouge. He screws with true love, and he closes down the world's best whorehouse. Asshole.
Jeremy Irons as Scar in The Lion King. "Here's an idea! I'll murder my brother and convince my nephew it was his fault, all so I can get the throne! Am I Claudius? No, I'm a frigging lion in a Disney film!" The fantastic dark character design and animation matched with Iron's impeccable voicework is what really makes Scar such and asshole.
Hal Landon, Jr as Captain Logan (Ted's dad) in Bill and Ted's Excellent Adventure. He doesn't care about the future of his son's band, and therefore he doesn't care about the future of the universe. He'll sell his son to military school in an instant. And he doesn't even bang a hot blonde who went to his son's high school.
Anthony Hopkins as Hannibal Lecter in The Silence of the Lambs. He's smart and he's ruthless. Clarice Starling has privileges only because he allows her to. He is a genius and he twists Agent Starling's mind into whatever position he wishes to.