Random Hateable Villains In Silly Comedies (17 items)

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  (#1) Regina George

  • Mean Girls

  It's a truly impressive villain that can befriend the protagonist, never letting on that deep down she's set on destroying them. But Regina George (Rachel McAdams) pulls it off through a bevy of three-way phone calls, fake compliments, and of course, the burn book. Plus there's nothing quite as daunting as a villain who can roll with the punches and make cut-outs cool.

  But an unintended consequence of Regina's manipulations is the creation of the monster within good girl Cady Heron (Lindsay Lohan). And while the whole school makes nice at the end, we don't think an afternoon of lectures about friendship and womanhood from Mrs. Norbury (Tina Fey) is enough to permanently quell Regina's evil. 
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  (#2) Shooter McGavin

  • Happy Gilmore

  Apparently the golf course is a breeding ground for villains.

  Shooter McGavin's (Christopher McDonald) beef with newcomer Happy Gilmore (Adam Sandler) is that he is threatened by the hockey player with amazing driving skills, but Happy's uncouth antics and his party crowd following don't help the matter.  

  Despite his willingness to play dirty by buying Happy Gilmore's grandmother's house or having Happy run over with a car, Shooter ends up losing in the end, much to the delight of us all. 
• 

  (#3) Judge Elihu Smails

  • Caddyshack

  Judge Smails (Ted Knight) from Caddyshack embodies the rich and entitled. He's obsessed with demonstrating his own status, as shown in every interaction he has with the club's staff. He is also threatened by newcomer Al (Rodney Dangerfield), who throws money around with zero cares given to social decorum and country club etiquette.

  The not-so-honorable Smails abuses the power he lords over caddie Danny Noonan (Michael O'Keefe), who is hoping to win the caddie scholarship to pay for college. The biggest flaw about Smails is that he acts as if enough brown-nosing and lugging golf clubs will up Danny's social class in life to be "on par" with his own (pun obviously intended). Judge Smails is clearly not a self-made man, and his disgust towards the gaudy and nouveau-riche Al proves that he will never accept an outsider in his club or as his equal.  

  Still, much of the fun of Caddyshack is owed to Smails, as nothing is quite as satisfying as watching his eyes bulge out of his overly tanned head.
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  (#4) Ed Rooney

  • Ferris Bueller's Day Off

  Any adult who is this involved in the life of a random teenager needs to reevaluate their decisions.

  In Ferris Bueller's Day Off, Ed Rooney (Jeffrey Jones) commits actual prosecutable crimes (trespassing, animal cruelty, threatening a teenager girl in her home with a weapon) in an attempt to nab Ferris for skipping school, which, last we checked, isn't illegal.

  Going opposite a protagonist as likable as Ferris Bueller, Principal Rooney just comes off that much more unlikable. Rooney was the kid who never had fun in high school, grown up to resent anyone who does, making his sole mission in life to be the biggest buzzkill of all time.

  Watching this stick-in-the-mud literally get stuck in the mud, though, is a downright gleeful experience.
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  (#5) Bill Lumbergh

  • Office Space

  Bill Lumbergh's (Gary Cole) villainy as the office boss is subtle, and thus all the more infuriating. His bland and banal voice alone is enough to push any cubicle worker into an embezzlement scheme.

  Lumbergh probably resonates so well as a villain because a lot of us have experienced a Lumbergh-esque supervisor - a boss who lurks around corners and doles out irksome demands to employees as if they're pals. It's also unclear what he does on a day-to-day basis other than fire employees and walk around relaying memos he's already sent. He makes one yearn for the more outright villains who at least give it to you straight. While unfortunately we don't get to see any revenge taken against Lumbergh's person, Milton (Stephen Root) eventually burns down the building and all the TPS reports with it.
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  (#6) Derek

  • Step Brothers

  In Step Brothers, step-siblings Brennan Huff (Will Ferrell) and Dale Doback (John C. Reilly) are so regressed that viewers might find it hard to root for them, if not for Brennan's smarmy brother Derek (Adam Scott).

  Derek conducts family singalongs, monopolizes every conversation, and appears to have a grudge again the duo. Like a lot of villains, Derek makes some good points. Brennan and Dale's relationship and living situation is codependent and odd. But even after Brennan abandons Dale, gets a job, and commits to a Range Rover lifestyle, Derek continues to bully his little brother and unfairly fires him, proving that a one-upper like Derek will never be satisfied.
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  (#7) Hedley Lamarr

  • Blazing Saddles

  What makes Hedy... ahem, Hedley Lamarr (Harvey Korman) despicable is that no deed is too lowly for him to pass up. Whether it's utilizing brutes to take down a town or attempting to pay the student price for a movie ticket, no underhanded feat is too big or too small for Lamarr's villainy.

  Even as he bands together divisive groups of bad guys for one evil cause, Hedley makes for a uniquely entertaining villain. His frivolity towards his own agenda and his repeated failures at even the most basic villain behavior make him an entertaining villain.
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  (#8) White Goodman

  • DodgeBall: A True Underdog Story

  White Goodman (Ben Stiller) might hate dodgeball team the Average Joes, but deep down, he really just hates himself. Depriving himself of processed sugar over the years has made him a pretty grumpy human being. Goodman doesn't actually care about owning Peter's (Vince Vaughn) gym - he just wants to take down the misfit establishment that caters to everyone, as he is threatened by the rival gym.

  Still, Goodman is never a boring villain. His white leather suits, inflatable codpiece, and odd relationship with food make him memorable, to say the least.  
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  (#9) Agatha Trunchbull

  • Matilda

  Why do so many adolescent-hating villains insist on careers in education? 

  The character of Agatha Trunchbull (Pam Ferris) is pretty dark for a family comedy film. As a school principal, she locks students in a cabinet, force-feeds them chocolate cake, and hurls them impressive distances by their hair. She's absolutely terrifying. Trunchbull lacks any redeeming qualities, save for the fact that her punishments are creative, making her entertaining.  Even the lovely Ms. Honey (Embeth Davidtz) is helpless against her, and the discovery that Ms. Honey is her niece and ward makes us hate Trunchbull all the more.
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  (#10) Eric Gordon

  • Billy Madison

  Part of what makes Eric Gordon (Bradley Whitford) so detestable is that he never proves himself to be anymore qualified to take over Madison Hotels than Billy Madison. Rather, he's just as juvenile as Billy with none of the penguin-chasing charm.  

  Gordon isn't exactly wrong about Billy Madison and his inability to run a company, but he doesn't actually care about the company - just himself. In the final quiz-off, all Gordon has to do is answer a question about business ethics. As a smarmy businessman, or just a person with business experience, he should be able to answer this question. But since he lack ethics, he can't respond.  

  His loss is our win. The company is signed over to Carl as Billy enrolls in college to further his education.
• 

  (#11) Zachary 'Sack' Lodge

  • Wedding Crashers

  It's unclear what Claire (Rachel McAdams) ever saw in Zachary, except for Bradley Cooper's handsome face. He does some pretty unlikable things, including repeatedly tackling opponents in a touch football game, yelling at his fiancee like a child, and beating up John (Owen Wilson) while his crew of cronies holds him down. But is anything worse than the sea otter impression? 

  Truth is, most of us probably have friends or family who've dated a Sack, or worse, we've dated one ourselves. They seem perfect on paper, but something is awry. His wealth, privilege, and fake philanthropic endeavors appear to make him a good match for the Cleary family, but his particular brand of crazy is too cruel. It is satisfying when Claire makes the right choice at the end.
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  (#12) Dean Vernon Wormer

  • National Lampoon's Animal House

  Should the Deltas be kicked off campus? Maybe. But Dean Wormer's (John Vernon) vendetta seems a little extreme. He's determined to kick the fraternity off campus even before Otter (Tim Matheson) sleeps with his wife, suggesting his involvement is nothing more than a power trip against a group of students who don't adhere to his uptight rules and regulations.

  His decision to expel the individual Delta members from Faber even after revoking their charter is overkill, so the audience takes great pleasure in watching his plans backfire tremendously.  
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  (#13) Mr. Walters

  • 21 Jump Street

  For most of of 21 Jump Street, Mr. Walters (Rob Riggle) is just a high school gym teacher (a familiar villain trope) who seems generally volatile. He turns out to be much more sinister, however, when's he's revealed to be the school pusher and takes Molly (Brie Larson) hostage.

  Mr. Walters doesn't have the bravery of his kingpin peers as he weasels his way out of a skirmish he started. Nothing's worse than a cowardly villain who can't even face up to their own crimes.
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  (#14) Rachel Phelps

  • Major League

  There's nothing more unforgivable to Americans than a bad a baseball game. In Major League, Rachel Phelps (Margaret Whitton) sabotages an entire season just so she can move the team to Miami, which offers her sun, sand, and a brand new stadium. While the draw of the Sunshine State is understood, to orchestrate a losing season at the cost of the players and their careers seems a bit dramatic and fairly evil.

  What makes Phelps unlikable is that she concocts the plan behind the backs of the players and coaches, allowing them to stew in the embarrassment of failure. She treats her team with indifference and disrespect, which makes her all the more repellant. 
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  (#15) Fred O'Bannion In 'Dazed and Confused'

  The high school hazing in Dazed and Confused is mostly fun, but Fred O'Bannion (Ben Affleck) takes it to another level. He is a terror to the new crop of freshman, gleefully paddling them to the point of frenzy. 

  He's a menace who thrives on fear, and no amount of '70s fashion can redeem him. It is all the more fun to watch him fall from grace at the hands of crafty freshmen with a handy can of paint. 
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  (#16) R.J. Fletcher In 'UHF'

  Working for a television network might seem great until you meet the likes of R.J. Fletcher (Kevin McCarthy) from UHF. When he isn't randomly berating staff or firing employees for his mistakes, Fletcher goes after the rival Channel 62, which George ("Weird Al" Yankovic) and Bob (David Bowe) have turned into a ratings horse thanks to janitor Stanley (Michael Richards).

  What's alarming about Fletcher, aside from his bipolar shifts from yelling to maniacal laughing, is that his disdain seems to stretch beyond his employees and his competition to most humans in general. He seems to genuinely consider a good deal of the population unworthy of life, which makes his takedown by the UHF team all the more satisfying. 
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  (#17) Evan Baxter

  • Bruce Almighty, Evan Almighty

  Everyone's got a coworker like Evan (Steve Carell). They get the promotion you deserved, they take credit for your work, and they always seem to come out on top despite their actions. Evan is not unique in his villainy, which is what makes his success so frustrating.

  Therefore, watching Evan become a puppet for Bruce's (Jim Carrey) amusement as he acts like a lunatic on live television is both entertaining and a fulfilling fall from grace.

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