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.