The Biggest Douchebags Of The Last 25 Years In Film
I’ve always had a theory that 1999 was the best and last year of great teen movies if you don’t believe me, just IMDB it. American Pie, 10 Things I Hate About You, She’s All That, Cruel Intentions, Never Been Kissed and a few others all came out in theaters that year. But along with them, a slew of teen douchebags were born.
After going to see The Social Network a couple weeks ago, I was again reminded of that slick talking, douchey face making breed of characters on film who (unluckily for us) exist in real life too. For example, think of Justin Timberlake‘s portrayal of Napster founder Sean Parker or The Winklevoss twins yes I capitalized ‘the’ and no, I can’t decide who is more douchey. These are the scripted characters who have made it OK for men on lacrosse teams to thrust their hips likes animals after scoring a goal (see: Stifler, American Pie) and draw male body parts on nerdy kids‘ cheeks while they are fully conscious. We’ll let you guess the reference on that one. Check out our list of the most douchey characters we’ve luckily encountered through our tv screens and not in our actual social spheres, below.
The Social Network – It’s a tie between The Winkelvoss twins (Armie Hammer)
and Sean Parker (Justin Timberlake)
Since I can’t decide who is more douchey, I’ll make a case for both. For the Winklevoss twins: row crew, gel hair, look like a real-life Ken doll, have gotten everything they ever wanted in life (minus Facebook) and use “our father” in a terrifying amount of sentences. I’m going with a 99% chance of douchey-ness. Sean Parker: the perfect portrayal of a slick-talking, teen girl pouncing, egotistical narcissist. What’s another word for douche?
She’s All That – Dean Sampson (Paul Walker)
Paul Walker (as hot as he is) is one of those actors who you look at and just assume has played douchey guys his entire life. In She’s All That, Walker’s character is the instigator of the bet that brings super jock Zack Siler (played by Freddie Prinze Jr.) to nerdland in the attempt to turn Laney Boggs into the prom queen.
Pretty In Pink – Steff (James Spader)
Probably my favorite of all the movie douchebags (and by favorite I mean the one who I’d most like to take out with a car in the high school parking lot) Steff is that guy who dated all the sluttiest, bitchiest girls in high school, wears head-to-toe white suits and shirts unbuttoned down to his belly button and talks with the most condescending (and irritating) slow drawl you’ve ever heard. Above is the “Steff edit” for your viewing pleasure.
American Pie – Steve Stifler (Sean William Scott)
Guys on lacrosse teams with adult ADD and pent up sexual energy are never a good combination and Steve Stifler is the ultimate proof. The basic lesson here is this: no one should move their hips in ways that that you could mistake for a scene on Animal Planet.
Wedding Crashers – Zachary Lodge (Bradley Cooper)
Before Bradley Cooper stole our hearts in He’s Just Not That Into You (OK maybe not our hearts in this one) and The Hangover, he played Zachary Lodge, the douchey fianc to Rachel McAdams’ Claire bear. But to his credit, anyone cast alongside a Vince Vaughn Owen Wilson duo can’t help but look bad.
10 Things I Hate About You – Joey Donner (Andrew Keegan)
Skip to 2:19 to see Andrew Keegan in all his douchebag glory as white tux-wearing Joey Donner (seriously, what is it with the head-to-toe white on these guys??)
Legally Blonde – Warner Huntington III (Matthew Davis)
Anyone with the name Warner Huntington III who plans to go to Harvard and run for senator some day is bound to be an asshole, just saying.
The Holiday – Jasper (Rufus Sewell)
Jasper is that guy who dates you, cheats on you, gets engaged in front of your face, still pretends that he loves you and then begs for your forgiveness all with the most conniving mix of charm and deceit. When said guy performs such acts on a woman as sweet as Kate Winslet, we definitely can’t forgive. We don’t hate a lot of people, but these types might be an exception.
Clueless – Elton (Jeremy Sisto)
“Do you know who my father is?” Anyone who asks this question should take a train straight to doucheville. You might have to trust us on this one, or rent Clueless this weekend to find out for yourself, because we could only find a non-speaking clip of Elton at 0:58 of this trailer for the film.
The Wedding Singer – Glenn Gulia (Matthew Glave)
No one with a name like Glenn Gulia has the right to treat others like dirt, but this one still forges into ultimate dirtbag territory, hitting on strippers at clubs and treating Drew Barrymore’s character Julia (soon to be Julia Gulia cringe) like his slave. Also, may we note white jacket alert! Do we spot a male douchebag trend in the making?
