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Ultimate on-screen heartbreakers

From The Virgin Suicide's Trip Fontaine to Sebastian Valmont from Cruel Intentions, we chart the hottest on-screen heartbreakers in response to the Paris menswear shows

Heartbreak comes in many forms: from straight out abandonment (The Virgin Suicides) to murderous revenge (Wild Things), and this season, Wooyoungmi took the 90s heartbreaker to the runway for SS15, with models dressed in baggy jeans, bucket hats and mesh polos. In a love-letter to all things anguish and despair, we select the boys that we wouldn't mind pushing our hearts through a metaphorical blender for.


Perhaps no colder tale of heartbreak than that of Roger Kumbles 1999 film Cruel Intentions, where a pair of sex-hungry step siblings seduce their way through high school. Among an array of iconography; Kathryn Merteuil’s (Sarah Michelle Gellar) cocaine-filled Catholic pendant, a 90s hit soundtrack of Placebo and that kiss between Kathryn and Cecile (Selma Blair), it is “completely fucked up” Sebastian Valmont (Ryan Phillippe), who takes the film’s crown as the ultimate heartbreaker, that is the most memorable. While initially vying for Annette’s virginity (Reese Witherspoon), Sebastian betrays himself by falling in love with her. However, humiliated by Kathryn, he quickly rejects Annette after sleeping with her and breaks up, revealing, “You mean nothing to me. You were just a conquest”. Stone. Cold.


“All the girls at our school were in love with Trip. All the girls except for Lux,” begins Sofia Coppola's 1999 film The Virgin Suicides. Unravelling the story of the unattainable and ultra mysterious Lisbon sisters who have spellbound the neighbourhood boys, it is Lux Lisbon’s (Kirsten Dunst) heartbreak at the hands of Trip Fontaine (Josh Hartnett) that drums up those highschool memories of teenage lust and ultimate anguish. After sleeping with her on the football field during prom night, the heartthrob leaves a sleeping, ethereal Lux to wake up, still on the field, on her own. The act perhaps provides a tragic factor in the sister’s undoing and eventual suicide, to which years later Trip reminisces, “She was the still point of the turning world, man. I never got over that girl. Never."


Xavier 'X' Red (Johnathon Schaech) in Gregg Araki’s 1995 film The Doom Generation certainly has all the traits of the heartbreaker: handsome, arrogant and born with absolutely no moral compass. When angsty couple, Amy Blue (Rose McGowan) and her slightly wimpy boyfriend Jordan White (James Duval) run into badboy Xavier – whom they nickname X – the night ends in the trio accidentally killing a gun-toting store owner threatening to shoot them for being short $6.66 (ominous much?). On the run, a triangle of sexual tension develops and although he doesn't actually break any hearts, X kind of fucks things up between the two lovers, especially when they engage in a threesome that ends with Jordan getting his privates chopped off with gardening shears, courtesy of a gang of intruding Neo Nazis. Go figure – but in the meanwhile see where it all started. Green spewing severed head included.


Jordan Catalano (Jared Leto) is the low-achieving, damaged badboy in cult TV series My So-Called Life. So, naturally he’s also the object of Angela Chase's affection (Claire Danes). All big, blue eyes and floppy hair, Jordan is that boy that leaves those indelible markings on your school notebook – and on your heart – which also means he’s kind of a jerk, too. As Angela approaches that crippling "Should I sleep with him" phase – or as she calls it "umm'ing" – the fallout ultimately leads to the biggest douchebag move ever when Jordan breaks up with her because she decides to abstain from sex with him. It gets worse when Jordan explains he never even wanted to get involved with her because he knew this would happen (harsh), "Because you don't get it, okay! You're supposed to! It's accepted! It's what you're supposed to do. Unless you're like... abnormal," he huffs. Okay, not even that knee-weakening colour trio of blue can save you now, Catalano.


If John McNaughton's Wild Things (1999) didn't get your heart beating then we're not sure what will. In a film that divides equal attention to sex as it does scandal, Matt Dillon plays hunky teacher Sam Lombardo, whose class pets are the dangerously minxy teenage Kelly Van Ryan (Denise Richards) and Suzie Toller (Neve Campbell). The trio’s twisted plan to make it rich involves a fake sexual assault claim from the girls followed by an even quicker retraction. Ching! Ching! Defamation payout. Unfortunately, it all turns a bit sour for Suzie when Kelly and Sam decide that "Two's company. Three's a crowd," as Sam ominously tells her, Champagne in hand, "This is a celebration, Suzie, not a suicide pact," before bottling her over the head, ultimately breaking her heart... and probably a few bones. Hot.


Billy Brown is the anti-heartbreaker. A guy who – after writing cheques that his wallet couldn't cash – is straight out of jail and back into trouble. Free for about five minutes, Billy takes the opportunity to kidnap Porcelain doll-looking, dancer Layla (Christina Ricci) with the plan that she meets his parents and plays the part of his perfect wife, the one that he has been writing to them about while incarcerated. At Billy's parents’ house, Layla, still in glitter tap shoes, obediently obeys, revealing, "I fell in love with him the first time I met him". For Layla, the phoney sentiment soon resonates more deeply as we see the blonde beauty’s continued advances towards an emotionally depraved Billy knocked back (spoiler: they get together in the end). More a 'treat em' mean, keep em' keen' kind of guy, without even trying to be.


Although being panned for bearing very little resemblance to the book of the same name, Less Than Zero (1987) plays out in the over-indulgent and exuberant city of Beverly Hills, where the pin up heartbreaker comes in the form of Robert Downey Jr. The cigarette smoking, quiff-rocking badboy-slash-drug-addict breaks his own best friend's heart when he sleeps with his girl (oops!). However, Julian's status as heartbreaker quickly goes downhill when he is forced to become a male prostitute after succombing to an unaffordable heroin addiction. Still, who doesn't love a troubled badboy…


If the name Sean Bateman (James van der Beek) sounds familiar to you then that’s because Roger Avary’s 2002 film The Rules of Attraction gives American Psycho’s Patrick Bateman’s little brother room to roam through college, indulging in a life fueled by sex and drugs. Although in love with the virginal Lauren Hynde (Shannyn Sossamon), Sean sleeps with her less-virginal roommate Lara (Jessica Biel) instead. When Lauren walks in on a naked passed out roommate and a pants-down Sean, Sean feels like it's a good time to admit his true feelings, “I only did it with her because I’m in love with you”. Classic.


Although in the business of street hustlin’, that doesn’t stop Scott Favor (Keanu Reeves) from breaking a few hearts. In Gus Van Sant’s 1991 film My Own Private Idaho, the young prostitute sleeps with best friend and fellow hustler Mikey Waters (River Phoenix). But when Mikey admits that he’s in love with Scott, asking him “What do I mean to you?” Scott tells him they’re good friends. A clearly upset Mikey, with his low voice and eyes fixed on the ground as he draws in the dirt reminds us all of just how tough ‘those’ conversations are. At least Scott offers him a hug...


The washed-up popstar from Allan Moyle's 1995 film Empire Records Rex Manning (Maxwell Caulfield) definitely got his heartbreaker tag from his (questionable at that) popstar accolades, as opposed to his looks. However, that doesn't stop a clearly besotted Corey Mason (Liv Tyler) from pursuing the star when he arrives at the Empire Record store for "Rex Manning Day". Offering herself up to Rex during his lunch break, the crude popstar responds with "I hope you like the taste of blue cheese," causing Corey to run from the room crying. But here's where the real heartbreak comes in, in a classic tale of best friend betrayal, it's Corey's BFF Gina (Renée Zellweger) who in fact ends up sleeping with the aging star. Bitch.