The 12 Douchiest Movie Boyfriends

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The 12 Douchiest Movie Boyfriends

By Courtney Enlow | Seriously Random Lists | December 4, 2012 | Comments ()


Much like last week for child stars, this week has been a highlight in the world of assface boyfriends and ex-boyfriends. He Who Shall Not Be Named But Is A Total Fuckernutter rejoined Twitter after a brief respite following an altercation during which he threatened to "shit right on [comedian Jenny Johnson's] retina." (Guys, I'm starting to think he might have issues with women.) Then, on Sunday, Rob Kardashian (*shakes head*) released a slew of tweets about how ex-girlfriend Rita Ora (I didn't know her name either but she sings that song that makes my eye twitch about "party[ing] and bullshit" that I totally thought was about "party[ing] and mulching." Which disappointed me because there aren't nearly enough shitty pop songs about gardening.) cheated on him and "let" him get her pregnant. Said tweets led to the trending topic "Rita Whora." Clevah girl. The irony of the lesserest member of a family empire built on a golden shower video calling a lady's virtue into question not withstanding, the point here is that some boys are ewey gross icky butt and my daughter's not allowed to date ever. With that, let's take a look back into some of the assfaciest boyfriends in some of our favorite movies.

(Note: I've received some criticism in the past for use of the term "douche" as a derogatory term due to a perceived misogynistic connotation. I, however, am of the belief that "douche" is the perfect term for the dickiest gents among us, for, like douches, they are bad for women and wholly unnecessary, and they will probably give you the crotch rot. Also, for obvious reasons, I've elected not to include scary violent murder boyfriends from horror or thriller flicks because they totally throw off the curve. Otherwise, y'all know what would have been on here. On with the list.)

Robbie "The Creep" Gould, Dirty Dancing


Sack Lodge, Wedding Crashers

Andy, Wet Hot American Summer


Roy Stalin, Better Off Dead


Gideon Graves, Scott Pilgrim vs. the World

David, An Education

That Fuckin' Footloose Guy


John Bender, The Breakfast Club

Mr. Sheldrake, The Apartment

Dante, Clerks

JD, Heathers

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Comments Are Welcome, Bigots and Trolls Are Not

  • DarthDarqeaux

    Scott Pilgrim himself was a serial douche. That qualifies him as a bigger douche than all seven evil exes combined.

  • Nicole

    I'll forgive the oversight of William Zabka since this is a list of "douchiest boyfriends" and not bullying, evil-spawn boyfriends but come on!

    Here is Billy's resume as proof he is one of the most horrible boyfriends in film history:

    The Karate Kid - Johnny Lawrence

    Just One of the Guys - Greg Tolan (ok, technically not the boyfriend)
    National Lampoon's European Vacation - Jack
    Back to School - Chas Osborne

    I think Johnny Lawrence could easily replace John Bender on this list. Bender is not a douche and he's not really a boyfriend either. He just has lots of girls he hangs out with.

  • Chip Douglas

    I don't know if he counts as a boyfriend but I think he deserves at least an honorable mention, Owen Wilson in the Cable Guy. Amazing!

  • Fuckin' Heathcliff, the assfaciest assface EVAH.

  • Sara_Tonin00

    c'mon, Rutherford was assier than Heathcliff.

  • zeke_the_pig

    'Sack Lodge' is still one of the best names ever.

  • jcoa2

    Craig Kilborn was so splendidly vile as Ellen Pompeo's boyfriend in Old School, it seemed for a moment like he had found a niche in movies. But only for a moment.

  • e jerry powell

    I have a niche for Kilborn. It's called the eighth circle of hell.

  • TheGreatUnstainer

    No Jareth the Goblin 'Gaslighting Boyfriend Metaphor' King?

  • Even Stevens

    I know you already had one Kevin Smith entry, but I feel Brody from "Mallrats" deserves honorable mention

  • A modest proposal: Rob Gordon, High Fidelity

  • ed newman

    No Mike Damone?

    On the other hand, side one of Led Zeppelin IV. So it's a tough call.

  • Danar the Barbarian

    One afternoon in the pool changing room does not a boyfriend make.

  • pcloadletter

    I find this list's lack of Hardy Jenns from Some Kind of Wonderful disturbing.

  • lowercase_ryan

    Back off Dante, he wasn't even supposed to be there today.

    But he does suck and can't cover the point. OK, he's a douche.

  • Jezzer

    He wasn't a douche for the "37 dicks" reason. The point was that his girlfriend was freaking out about his past sexual history and acting betrayed because he had slept with a handful of other girls before he met her, but didn't think it was as big a deal that she had blown her way through half the town.

  • e jerry powell

    Only half? She's a slow worker, apparently, and could stand to build up her efficiency numbers. 37 is nowhere near true dirty slut league.

  • lowercase_ryan

    I think he was a douche because he had a great girlfriend who loved him but that he constantly disrespected by being hung-up on Caitlin "Stiffy" Bree.

    I added the stiffy. Cause dead guy.

  • mister_hud

    This post was copied from a Redbook article from a few years back I think

  • BlackRabbit


  • BendinIntheWind

    I'd also humbly submit Tim Robbins' character in High Fidelity, provided that he's subcategorized in the Paul Rudd vein of hilarious douches.

  • Javier

    whoa, hold the phone! his name is Rob Kardashian?!

    I always thought it was Knob!

  • e jerry powell

    I've never seen anything of him but his badonkadonk, so I can't say anything for sure.

  • Puddin

    John Bender wasn't a douche, he was misunderstood. His father gave him cigarettes for Christmas. Don't worry-I can change him.

  • the dude

    Smoke up' Johnny!!

  • InternetMagpie

    Oh, PUDDIN'.

  • InternetMagpie

    Oh, Mister SHELDRAKE. The original negguy.

    Or maybe that would be Ingrid Bergman's husband in Gaslight?

  • Nicole_OCTV

    I will never pass up an opportunity to post a link to my favorite all-time Paul Rudd movie clip (from Wet Hot):

  • pumpkin

    My favorite as well. It's perfect.
    (and I went to/worked at a Jewish summer camp in the 1980s, so I'm an expert).

  • PerpetualIntern

    This clip ALWAYS makes me laugh. Always. This whole movie just makes me so happy

  • Sara_Tonin00

    Guys get hot brunettes and we get douchy pretend boyfriends?

    sounds like real life.

  • mairimba

    Wait. The hot brunettes post was just for the guys?

  • e jerry powell

    I say you can have the brunettes if you want 'em. I'm certainly not using them in this particular moment.

  • In fairness, several of them *are* hot brunets. (Is that how you spell the masculine? It occurs to me I've never actually seen it written. Sexism maybe!)

  • Danar the Barbarian


  • BendinIntheWind

    I think "brunts" would be appropriately masculine.

  • hindulovegod

    Prince Humperdinck was a crappy boyfriend. And Joe in Say Anything. Joe lies!

  • AngelenoEwok

    Is a guy who forces you to live in his castle and be his fiancee really a boyfriend though?

  • Rosanna

    It is when he plans on murdering you on your wedding night AND plans to blame it on Guilder. Poor Guilder.

  • "Like you and she were ripped apart. Like JOE AND I were ripped apart."

    I've long had a Best Best Friends list a-brewin'. Corey wins it.

  • petitesuissesse

    Joe certainly lies when he cries. That douche.

  • e jerry powell

    I think I know Heather a bit better than you, okay? If she was going to slash her wrists, the knife would be absolutely spotless.

    You have to admit, Veronica had her annoying moments, too.

    And Dante, may I ask, what is wrong with sucking 37 dicks?

  • Jezzer

    It was the fact that she was angry with him for sleeping with like 3 other girls before he met her.

  • e jerry powell

    I've got 'em both beat, and no one is mad at me about it, either.

  • Natallica

    John Bender was a douche... but so crush-inducing!. At least for the teen I was when I saw that movie.

  • ,

    "a family empire built on a golden shower video

    And here, I thought it started with their dad getting a double murderer off Scot-free. No one would have heard of these idiots otherwise.

    As always, I blame O.J.

  • Bedewcrock


  • e jerry powell

    I'm suing you for the cost of the oxygen tanks I'll need now that I've fainted.

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