What would a great comedy be without a memorable villain? Nothing I tell you! More often than not, villains offer some of the best quotes and scenes in the movie. They must maintain a level of cruelty which makes you side against them, while maintaining a heightened level of absurdity, making them easy to laugh at. What would Happy Gilmore be without Shooter McGavin? Or Zoolander be without Mugatu? Here we take a look at the greatest comedy movie villains of the past 20 years!

Derek — Step Brothers (2008)

The over-achieving, “Sweet Child O’Mine” family singing, perfect older brother, Derek is every bit more grown up than his brother, and new step brother. But there’s just one thing about him, he’s a total tool! He resorts to telling you how much money he makes every year, and unbeknownst to him, he can’t satisfy his wife for squat.

Bill Lumbergh — Office Space (1999)

Lumbergh represents all things corporate a**hole, from the belt AND suspenders he wears, down to the Porsche he drives with the vanity “My PRSHE.” Not to mention he spouts off nothing but unenthusiastic detached corporate jargon: “What’s happening?” “Mmkay,” and “That’d be great,” all of which just heighten how little he actually cares about his employees.

Wes Mantooth — Anchorman: The Legend of Ron Burgundy (2004)

Lead anchor of the KQHS Channel 9 news, Mantooth is the rival of Ron Burgundy. He is rather insecure of his second in the ratings position, and overly protective of his mother, Dorothy Mantooth, which makes for great comedy, because he is the one who initiates the infamous anchorman battle.

Lois Einhorn (Ray Finkle) — Ace Ventura: Pet Detective (1994)

“Einhorn is Finkle, Finkle is Einhorn!” As viewers we spend the majority of the film believing that Einhorn is the head of the police investigating a murder and the disappearance of Snowflake the Miami Dolphins mascot. We later discover that she is in fact Ray Finkle, former Dolphins kicker, who’s out for revenge after failing to make a potential Super Bowl-winning kick all because Dan Marino doesn’t know that you hold a football “Laces Out!”

White Goodman — Dodgeball: A True Underdog Story (2004)

Goodman is the over-the top leader of the Globo Gym Purple Cobras who won’t allow himself the pleasure of junk food. With his band of American Gladiator-style men: Blade, Laser, Blazer, and Michelle, he is set out on making sure no one gets a piece of the pie. Literally.

Eric Gordon — Billy Madison (1995)

Gordon is the snakey, conniving, insecure jerk who wants to become CEO of Billy’s dads company, even though the final question of the Jeopardy-style academic decathlon proves that he isn’t the right man for the job. In the end, he is just a self-serving man who gets shot in the butt, and has weird looking balls.

Jacobim Mugatu — Zoolander (2001)

Perhaps the funniest comedy villain to look at, Mugatu makes outlandish claims to the people in his inner-circle. Like when he demands someone lose five pounds immediately, and when he yells at his assistant for not remembering that foamy lattes make him “farty and bloated.” Not to mention, he invented the piano key neck tie! I think that counts for something.

Dr. Evil — Austin Powers: International Man of Mystery (1997)

The ultimate Bond villain parody, Dr. Evil is a dim-witted criminal with dated motives and unrealistic threats (making all of the volcanoes erupt in the world at once, and using stock Independence Day footage to make the President believe he has blown up the White House).

Shooter McGavin — Happy Gilmore (1996)

McGavin is the ultimate arrogant, pompous, yet insanely insecure showman. He’s at his best/worst when he isn’t the center of attention, and is threatened by everything he isn’t. What he lacks on the course (a gold jacket) he takes out on the people who threaten him, such as purchasing Happy’s grandmother’s house to spite him, and hiring a heckler to make him play poorly.

Ernie McCraken — Kingpin (1996)

Ernie “Big Ern” McCraken is an above the law, sarcastic, scummy womanizing bowler with one hell of a comb over. He finds no problem in ditching Roy Munson the night he got his hand chopped off, and certainly doesn’t think there should be any problem when they reunite several years later at a bowling competition in Reno. And in the end, he’s proof that good guys finish last.