The comedy villain is one of the trickiest characters to pull off. Too often, the villain's scenes are there simply to further the "plot," which, in a lot of comedies, is pretty inconsequential. If a comedy even has a true villain, and many don't, scenes focusing on him or her usually drain the movie of life and make the audience eager to get back to the laughs. But a smart comedy creates a villain every bit as funny as the hero(es). Below are my favorite movie slimeballs, in order of release date. I'd love to hear some of yours.

John Vernon as Dean Vernon Wormer in National Lampoon's Animal House

One of the best traits for a comedy villain to have is that he or she is an "Enemy of Fun." You've met people like this. They hate fun. They hate people who have fun. Dean Wormer is a perfect example. In fact, unlike the other bad guys on this list, you can't imagine Wormer ever having had fun at any point in his life. Smileless, humorless, joyless...but hilarious. The crusty, bitter dean is almost a requirement for college movies, and you can feel Wormer's influence in every flick of its type released since. You certainly wouldn't have Dean Pritchard in Old School without Wormer. Animal House is a movie brimming over with jerks, Doug Neidermeyer would have made a perfectly good choice here, too -- frat guys always make great villains. But you've got to have some sympathy for that dude-- he got killed in Vietnam by his own troops.

Best Line: "The time has come for someone to put his foot down. And that foot is me."

Ted Knight as Judge Smails in Caddyshack

Stopping just short of actually chewing on pieces of scenery, Knight's work in Caddyshack is a masterpiece of taking it over the top. A master of the slow burn, the man is made of simmering anger and rage. Knight more than holds his own against three incredible comedians: Bill Murray, Rodney Dangerfield, and Chevy Chase in his prime. In a lesser movie, Judge Smails would be a generic authority figure, enabling the three comedy stars to do their riffs around him and act out against him. But Knight's Judge is a worthy opponent, and manages to grab just as many laughs as the goofballs. Every bit as influential as Dean Wormer, you can draw a straight line from Judge Smails to say, Shooter McGavin.

Best Line: "I've sentenced boys younger than you to the gas chamber. Didn't want to do it. I felt I owed it to them."

p>Thomas F. Wilson as Biff Tannen in Back to the Future

Any high school comedy worth a snot needs to have a great bully. And Biff Tannen is one of the meanest there has ever been. How many bullies can say they terrorized multiple generations? (And it doesn't stop there! When you watch the trilogy you learn that the Tannen family is a true legacy of assholishness).Tannen's crimes are a bit more severe than the others, he does attempt sexual assault after all, but it only makes his comeuppance all the sweeter. Is there a more triumphant moment in the high school genre than George McFly finally decking Biff Tannen outside of the "Enchantment Under The Sea" dance? I think not. I grew up watching the Back to the Future movies and praying there wouldn't be people like Biff when I got to high school. But of course there were. And there always will be.

Best Line: "Why don't you make like a tree and get out of here?"

***By the way, if you've ever wondered what the man who played Biff Tannen is up to these days, feast your eyes!

Jeffrey Jones as Edward Rooney in Ferris Bueller's Day Off

The best example of the "Enemy of Fun" character is surely Ed Rooney. So upset that one of his students is -- God forbid --enjoying life, he makes it his mission to leave school to track him down and put an end to it. And nothing will stand in his way, he even breaks into the punk's house! Jones' work is phenomenal here, the cheap suit, the bug eyes, one of the greatest ever movie mustaches, the guy is a principal. His interplay with his dim-witted secretary Grace (played by John Hughes staple Edie McClurg) is particularly sparkling. And typical Hughes genius, the film ends with the jerk receiving his ultimate punishment: having to sit on the school bus with the students he so despises.

Best Line: "I did not achieve this position in life by having some snot-nosed punk leave my cheese out in the wind."

Bill Murray as Ernie "Big Ern" McCracken inKingpin

I was a big fan of Dumb and Dumber, but I wasn't prepared for how aggressively funny the Farrellys' follow-up would be. And a big reason for its success is the performance by Bill Murray. I understand that many will consider it blasphemy to say so, but for me, this is Murray's funniest work. Every line is gold, and it figures -- according to the Farrelly Brothers, Murray would glance at the script and then do whatever the hell he wanted. The man makes such a powerful impression in the opening scenes of this movie, it's a true credit to the film that we don't even realize how much we miss him until he comes blasting into the finale even nastier and funnier. To this day, I have never laughed harder than during the climactic bowling tournament in this movie. Murray, covered in grease and sweat, wearing his ridiculous disco cowboy outfits (with back brace), rose-filled ball thrust into the air, combover flapping in the breeze, is the stuff legendary performances are made of.

Best Line: "Do me a favor, will you? Would you mind washing off that perfume before you come back to our table?"

Mike Myers as Dr. Evil in Austin Powers: International Man of Mystery

Dr. ("I didn't spend six years in Evil Medical School to be called Mister, thank you very much") Evil is the ultimate parody of a supervillain. He's obsessed not just with doing bad things but with "Evil" as a concept, as a way of life. And to make matters worse, he's a bad father! As funny as Austin Powers is, it's Dr. Evil who really steals the show. If you can make the audience look forward to the bad guy, you've really done something right. Dr. Evil doing the macarena, the "Sh!" fight, the sharks with frickin' lazer beams, there's an abundance of hilarity here. Myers sends up the Bond movie cliches better than anyone before or since: "I have an even better idea. I'm going to place him in an easily escapable situation involving an overly elaborate and exotic death."

Best Line: "The details of my life are quite inconsequential... very well, where do I begin? My father was a relentlessly self-improving boulangerie owner from Belgium with low grade narcolepsy and a penchant for buggery. My mother was a fifteen year old French prostitute named Chloe with webbed feet. My father would womanize, he would drink. He would make outrageous claims like he invented the question mark. Sometimes he would accuse chestnuts of being lazy. The sort of general malaise that only the genius possess and the insane lament. My childhood was typical. Summers in Rangoon, luge lessons. In the spring we'd make meat helmets. When I was insolent I was placed in a burlap bag and beaten with reeds -- pretty standard really. At the age of twelve I received my first scribe. At the age of fourteen a Zoroastrian named Vilma ritualistically shaved my testicles. There really is nothing like a shorn scrotum... it's breathtaking -- I highly suggest you try it."

Gary Cole as Bill Lumbergh in Office Space

The "Boss From Hell" is another comedy staple, but never has that character been brought so uncomfortably to life as in Office Space. Character actor extraordinaire Gary Cole's performance is so eerily specific and so deadly accurate that on my first viewing I almost couldn't laugh, it gave me such a chill of horrible recognition. The "Um's," "Yeeeeeah's," and "Mmkay's" that are the passive aggressive co-worker's calling card -- it's something everyone can relate to, but had never really been put onscreen before. When Peter Gibbons thinks his girlfriend has slept with Lumbergh, the audience is sickened right along with him. And when we see the incident "take place," with an oiled up Cole pumping away while drinking coffee, it's almost scream-inducing. One of the most impersonated film characters ever, you can't watch the film without trying out the voice afterward.

Best Line: "Oh, and I almost forgot. Ahhhh, I'm also gonna need you to go ahead and come in on Sunday, too..."

categories Cinematical