Entertainment
136 voters

The Most Perfectly Hateable Villains In Silly Comedies

March 31, 2020 1.1k votes 136 voters 2.1k views17 items

List RulesVote up the performances you absolutely love to hate.

Just because it's a comedy doesn't mean it's all sunshine and rainbows. These comedy movie villains sometimes make us laugh, but they also make us groan, scream, and maybe throw things at our TV. Some of these bad guys work their evil magic in style; for others, the journey isn't as smooth. Some are over the top, while others come across as more realistic. And while most get their comeuppance in the end, we will still root against them on the next viewing. At times they might be almost too insufferable to watch, but we can't bring ourselves to look away. These films wouldn't be the same without their villains, making them truly necessary evils.  

Photo:
  • 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. 

    102
    25
    Perfectly hateable?
  • 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.

    71
    10
    Perfectly hateable?
  • 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.  

    72
    12
    Perfectly hateable?
  • 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.

    72
    14
    Perfectly hateable?