The Worst Boyfriends In Cinema

Dump him already!


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This week, Bridesmaids brings us a stellar example of a dodgy movie bloke, with Jon Hamm’s preening, self-obsessed sex buddy who generally makes Kristen Wiig’s life a misery when he isn’t trying to get her to perform some outrageous erotic act. Which got us thinking about the feckless, useless, and sometimes downright dangerous bad boyfriends burped up by the movies. The message to women being thus: some of this lot may seem attractive, but they’re all trouble…

Played by: Jason Schwartzman

Movie: Scott Pilgrim Vs. The World

"All because the ladies love": His smooth hipster style, his ability to hang with the latest bands and the fact he owns at least two clubs, which means he’s not short of a bob or two. He’s handy with swords, so he’s good if someone tries to mug you, but since he travels in a limo, that’s not likely to be much of an issue.

"Look out, love!" Turns out most of his appeal is thanks to a nasty little mind-control chip that’s so selfish, it even has his omnipresent logo on it. He’s also smug, self-satisfied and frankly more than a little evil. Happy to turn friends against once another, he’ll then dial up his enemies to offer a mock-sympathetic phone call that's more mockery than sympathy.

Played by: Paul Rudd

Movie: Wet Hot American Summer

All because the ladies love: The fact that he’s the eternal bad boy, a man who likes to treat ‘em mean and keep ‘em keen. It works, too: he’s able to simultaneously romance hot camp counsellor Katie (Marguerite Moreau) and mack on the equally scrumptious Lindsay (Elizabeth Banks).

Look out, love! He’s a total tool, a prick of the highest order. Of course, given that Wet Hot... is a parody of summer camp clichés, he’s naturally ramped up, but a man who can call you a dyke then tell you he loves you within the course of one sentence? Run. Run far, run fast. Plus he acts like a four year-old when ordered to do anything useful, which means he’d be crap at DIY.

Played by: Jesse Eisenberg

Movie: The Social Network

All because the ladies love: He’s a swift-talking nebbish who’s grateful for female attention, which means he’ll try harder in some relationship cases. He also has the slightly enticing appeal of creating one of the most famous websites in history and becoming Scrooge McDuck-level rich off the back of it. If you can tolerate his social awkwardness, you’re set for life.

Look out, love! Just don’t expect any real respect, at least not until he’s learned a few lessons in life and love. His break-up with Rooney Mara’s Erica Albright is one for the ages, with Zuckerberg simultaneously correcting her speech and criticising where she studies. Plus, once she’s stormed off, he heads back to his dorm room and begins drunkenly slagging her off online. Cock.

Played by: Mark Wahlberg

Movie: Fear

All because the ladies love: Smouldering and dangerous = exciting! Especially to naive teen Nicole Walker (Reese Witherspoon) who hooks up with him. And for a while, it’s sexy (if you find being fiddled with on a rollercoaster stimulating) and intriguing, since he’s charming and protective. A little too protective, but boys will be boys.

Look out, love! The real trouble comes when Nicole realises quite what a bad seed our Davey boy is. When she tries to break up with him, he goes and becomes a crazed stalker, endangering all of Nicole’s family in the process.

Played by: Christian Slater

Movie: Heathers

All because the ladies love: New boy. Check. Rebel. Check. Hunky. Check. Jason Dean seems to offer it all. So when Veronica (Winona Ryder) discovers life with the cool, cliquey girls she’s been trying so hard to fit in with just doesn’t seem so appealing anymore, JD becomes the focus of her attention. He’s got ideas, that one...

Look out, love! ...Ideas which sadly reveal him to be a twisted psycho who loves to plot the deaths of anyone who crosses his path and frame it as a suicide. Soon he’s dragging an increasingly hesitant Veronica into his mad schemes. It’s so hard to connect with an apparent soul mate when you’ve had to fake your death, an act that makes him try to blow the whole school up in a fit of heartbroken vengeance.

Played by: John Cusack

Movie: High Fidelity

All because the ladies love: A more unusual one this, since he’s really supposed to be the sympathetic lead in his own film. And yes, he’s got the twinkly Cusack appeal, a massive record collection and an actual business and largely manages to sort out his relationship by the end. Plus he makes a killer mixtape.

Look out, love! But he’s also a whining, self-pity loser more attached to his precious music than any woman and seems more intent on tracking down why his exes dumped him than actually fixing life with current girlfriend Laura (Iben Hjejle). He may eventually be worth all the work, but frankly he comes across as a bit too much of a fixer-upper for many women to deal with.

Played by: Jonathan Rhys Meyers

Movie: Match Point

All because the ladies love: He looks like Jonathan Rhys Meyers, so if you don’t mind slightly mad, staring eyes, he’s a good catch. Plus he’s sporty, down-to-Earth and yet still able to mingle with all sorts of people. He manages to convince Emily Mortimer to marry him and works his magic on her rich family.

Look out, love! Sadly for Mortimer’s Chloe, he’s also the transport system for a wayward penis that then twitches off at any sexy filly that happens past. Or, in this case, Scarlett Johansson’s beauteous blond type. Naturally, he beds her (or maybe “fields” is the right word, since their first liaison happens outdoors), gets her preggers, then, er, fakes a drug break-in to murder her and cover up what he’s done.

Played by: Brad Pitt

Movie: Kalifornia

All because the ladies love: It’s another one of those archetypal bad boys, even if he does look a bit like a live-action version of Shaggy from Scooby-Doo. But many women love a ragged rebel they think they can change. And some, like Juliet Lewis’ Adele Corners simply find him exciting.

***Look out, love! ***Yes, he’s just overflowing with passion. Unfortunately, it’s a passion for murderlising people, and he’s not afraid to drag those around him into his diabolical schemes. So if he asks for a lift from you, even if you think he’ll bring some fun into your life, just drive away. Or try to run him over – it’ll be a lot less trouble in the long run.

Played by: Wes Bentley

Movie: American Beauty

All because the ladies love: He’s sensitive and arty, caring and thoughtful and also has access to some amazing pot. Ricky likes nothing more than to quietly film the beauty he finds in the simplest things. He’ll even help you out if you have a big problem with your dad. Just try not to upset his dad, the bigoted Marine colonel.

Look out, love! Um... He’s a bit of a voyeur, so chances are he’ll end up trying to videotape you in the altogether. Plus let’s face facts: the camcorder habit is more than a little embarrassing and his ideas on “art” and “beauty” are the worst kind of emo noodling. He’s mopey and passive, and creepy and he looks like Wes Bentley. Sorry Wes.

Played by: Chris Sarandon

Movie: The Princess Bride

All because the ladies love: We’re going to have to reach on this one a little, because he’s not exactly the world’s most appealing man and Robin Wright’s Buttercup only really agrees to become his fiancée because her beloved Westley (Cary Elwes) vanishes and is believed murdered. So what appeal does the sneery royal have? Well, he’s a prince, so he’s loaded. Look, even Prince Charles managed to get married, so it’s pretty clear that money + power is still a huge incentive.

Look out, love! He’s evil. He has a six-fingered enforcer (Christopher Guest) who likes to torture people in his employ. And he’s a petty, spoiled child who has no idea what romance is about or really how to treat anyone. He might be heir to the throne of Florin, but it’s not quite enough to overcome all his bad points.

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