The Devil Wears Izod: The Ten Greatest Preppy Villains

Posted by sometripe
There's something about pleated khakis and navy-blue blazers that gives us chills. Clearly we're not alone — the preppy villain has been a staple of Hollywood's light fare for decades. You can spot him (and it is always a "him" — girls like the Heathers were the same genus, different species) by his ascot and asymetrically parted hair, or perhaps the pink Lacoste sweater tied loosely across his shoulders. Sometimes he wears only tennis shorts, a polo shirt and a sneer. He had a big hand in popularizing feathered hair — that's how evil he is. The preppy villain hit his stride during the Reagan years (60% of our featured preppy villains are of the '80s), but he still pops up now and again, a magnet for our disgust so there's nothing left but love for the little guy.

10. Vice-Principal Gills, Summer School (1987)



Gills (Robin Thomas) plays a leisure-suit-wearing high-school VP who assigns his gym instructor, Mr. Shoop (Mark Harmon), to teach a remedial summer English course so he can spend the warmer months wooing the history teacher (Kirstie Alley). He serenades her with vintage convertibles and well-prepared picnics that include expensive fromage. Being the villain, he also tries to sabotage Shoop's class by loudly pointing out their inadequacies. Evil-prep quirks include dropping fancy French phrases like "joie de vivre" and expressing exaggerated horror at a clip of Texas Chainsaw Massacre before running from the room. — Liz Nadybal


9. Mick, Teen Wolf (1985)



Somehow, Scott Howard was only briefly fazed by the whole being-part-wolf thing. Yet Mick, his arch-nemesis and star of the rival high school's basketball team, threw his life into complete disarray. Mick could usually be found coordinating his denim-on-denim ensembles and inappropriately groping his girlfriend. When he wasn't playing point guard for the Dragons, he enjoyed creating clever quips about Scott, like "Hope your acting's better than your hook shot, kid." — LN


8. Zachary "Sack" Lodge, Wedding Crashers (2005)



Sure, Bradley Cooper's portrayal of Rachel McAdams' fiancé is over-the-top. But what do you expect from a plot in which McAdams' mother makes Owen Wilson feel her up and her sister jacks off Vince Vaughn under the dining room table? This is not a subtle movie, nor is Sack a subtle villain. He's designed to be the character you automatically hate, in direct contrast to Owen Wilson's laid-back butterscotch stallion and Vince Vaughn's affable teddy bear. He hunts quail with a vengeance, kisses senator ass, takes a game of touch football to death-match levels and wears the perfect rugby-shirt-and-Abercrombie ensemble for each occasion. His shining moment takes place at McAdam's sister's wedding to Vaughn, where the Sack tells Christopher Walken he "don't know shit" and orders McAdams to "get your fucking ass on that altar right now." We all cheer when Vaughn knocks him out. Nobody can disrespect Walken. — Nicole Ankowski


7. Patrick Bateman, American Psycho (2000)



I'd always imagined Christian Bale smelled of high-end grooming products like Kiehl's Rare-Earth Cleansing Masque, a preppie of the truly classy sort. Then I saw American Psycho, a Bret Easton Ellis adaptation in which Bale plays a slick Wall Street financier with a penchant for after-hours rape and torture, and Kiehl's suddenly seemed a bit twee. Still, Bateman has a Newport summer home, a prep-school diploma and a collection of Hugo Boss three-pieces we'd like to get our hands on. If he didn't insist on disemboweling people, we'd be in love. — Steph Auteri


6. Stan Gable, Revenge of the Nerds (1984)



Bright red short-shorts and feathered hair — we could never quite reverse that image of Ted McGinley, even after several years of his role as the girlish Mr. Marcy D'Arcy on Married...With Children. Nor the image of him tossing freshmen out their dorm windows after his frat house burns down, participating in a tricycle race, or pulling a jockstrap over the head of an Asian student while yelling, "Do you know karate?" Subtle! — Will Doig


5. Rand McPherson, PCU (1994)



Before he became the grizzled Dennis Finch on Just Shoot Me, David Spade played a pitch-perfect prep-frat leader, Rand McPherson, attending the counter-culturally diverse Port Chester University. Lackey to the university president, the sniveling Finch leads a group of Republican minions in a quest to rid the campus of binge-drinking, loud music and all things un-Izod. Obviously, he gets it in the end, locked into a room by Jeremy Piven with a stereo playing "Afternoon Delight" on repeat, though just locked in a room with Jeremy Piven might have been a more effective coup de grace. — SA


4. The tennis players, Trading Places (1983)
Philadelphia in 1983 was a septic system of crime and filth, so Louis Winthorpe III and his snotty friends played tennis at an upscale private club. Winthorpe's friends were the kind of old-money preps that almost don't exist anymore. They spoke with Katharine Hepburn accents and serenaded their female hangers-on with their Ivy League alma-mater song. They owned the kind of white tennis shorts that are now selling on eBay for triple digits. And they really didn't like prostitutes (Jamie Lee Curtis) or poor black people (Eddie Murphy). When Winthorpe loses his money, they drop him faster than you can say forty-love. By the time the second half of the film rolls around they've basically disappeared, but you have to assume they got cleaned out in that frozen concentrated orange juice debacle. — WD


3. Hardy Jenns, Some Kind of Wonderful (1987)



With his popped collar and visible-from-space chin dimple, Hardy (Craig Sheffer) was quintessential '80s prep: rich, philandering, ready to embark on a college career of date rape and a professional career of white-collar embezzlement. "He's a total buck," as one character describes him, and even at twelve, I didn't understand that. Writer/director John Hughes does have a tendency toward broad stripes, and he painted Hardy with an industrial-size rollerbrush. "You walk out on me, where you gonna go?" he snarls at his beautiful girlfriend, played by Lea Thompson. Into the arms of true love, of course. Enjoy your status car and your receding hairline, buck. — Sarah Hepola


2. Johnny Lawrence, The Karate Kid (1984)



I still can't watch that Halloween party scene, when Ralph Macchio is running for the chicken-wire fence in his crazy shower costume and the skeleton thugs pull him down and kick the stuffing out of him. Johnny Lawrence isn't even a preppy villain in the fun way. I knew too many of him in high school to be amused. In fact, nine-tenths of the pleasure of watching The Karate Kid is simply seeing Lawrence get that screaming-bird kick to the face. They should put that on a loop and play it repeatedly for unpopular high-school kids with low self-esteem. — WD


1. Steff, Pretty in Pink (1986)



James Spader's Steff was the ultimate preppy villain during a time when wearing silk dressing gowns at keggers was cool. He spends the entire movie trying to bed Molly Ringwald's friend Andie while keeping his best friend, pretty-wuss-boy Blane (Andrew McCarthy), from getting into her pants. Despite being fabulously dressed in pastels and shoulder pads, he imbues his character with enough quiet slime that you can understand why Molly recoils every time she sees him. Spader so inhabited the bad boy with the pretty face that it launched his career, and you can still see some Steff in most of his roles today. — NA
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Posted Nov 01 2007, 04:00 PM
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Comments

bilge said:

I guess somebody hasn't seen FUNNY GAMES...

November 1, 2007 8:11 PM

oh_amanda said:

i have to seriously thank/give you major props for including Mick (teen wolf).

always my favorite villain growing up.... followed in a close 2nd by Johnny Lawrence.

thank you nerve.

xxxx

November 1, 2007 11:49 PM

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