I appreciate a good villain and I really think that the best ones aren't the usual strawmen that are built up so our cardboard heroes can smite them with impunity. The guys I want to mention here are creations of both the actors and the screenwriters who created and developed these guys as our most loathed foils and to be honest, we KNOW these people and that is what makes them so delicious. I want to give a shout out to those folks that have done such a great job of giving us someone to hate that is so personal, which in turn, lends our heroes a bit more credibility. This list is totally subjective and exists merely as a way to allow others to contribute if they so choose.
He tops my list because he had two incredible performances in the 80's. First as the ass kissing local LAPD officer in Die Hard, a clueless, by-the-book plodder who immediately disregards anything coming from beneath his paygrade. Secondly as the burned out detention teacher from The Breakfast Club. Two incredible performances, you have no issues at all with loathing him and cheering for anyone who is in conflict with him. Also delightfully slimy in Trading Places and countless other roles. He's at the top of my list of guys you love to hate.
What can you say about this guy that hasn't already been said? Die Hard I and 2, Real Genius and Ghostbusters? Forever known as the "Man with no dick", thanks to Ghostbusters, he's got slimy down to an art. I could have listed him first, but Gleason does such a great job being a petty tyrant that I had to move Big Bill down a notch. Was there anyone in the audience who didn't smile when Bonnie Bedilia punched him in Die Hard? Didn't think so.
Bob does sinister extraordinarily well. In Shawshank redemption, as the warden, his malevolence and phoniness shine right on through without any glimmer of redeeming qualities. For those of you that aren't well acquainted with his talents, check out his turn as agent provocateur in Matewan. Bob has that gift of tone that sounds like a velvet glove with the fist of cruelty contained within.