Top 10 Douchebags in Romantic Movies

As a member of the so-called “richie” kids, Steff’s used to getting what he wants… Probably because he’s one of those well dressed, smooth-talking handsome types who’s never met a cigarette he doesn’t like. Based on his treatment of Ms. Pretty in Pink herself, Andie, we can see that he’s also manipulative, has little-to-no respect for women, and doesn’t seem to care for his friends all that much either. In classic douche fashion, he tries to conceal his feelings for Andie by saying terrible things about her when she refuses to be treated like a piece of his property. And if bullying and trash-talking people because you’re bitter isn’t a douche move, we don’t know what is.

In our first encounter with the villainous Tybalt in Baz Luhrmann’s take on “Romeo and Juliet,” we learn two things: he’ll point his gun wherever he wants, and he’s clearly using that gun to compensate for something else. Hey, when your confidence is built on nothing but a firearm and a famous family name, the label “douchebag” is bound to come up. Oh, and his greased hair, bad attitude and – hopefully ironic – holier-than-thou sleeveless shirt certainly don’t help. Tybalt can’t control his loud mouth or his temper, and perpetuates the family feud between the Capulets and the Montagues for a new generation – which, as you know, causes much woe for his cousin Juliet and her Romeo.

#8: George Wickham “Pride & Prejudice” (2005)

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Turns out, Jane Austen’s timeless story contains a timeless douchebag. Mr. Wickham introduces himself as a kind, generous, and suave military man. His handsome façade nearly ruins the Bennet family reputation, however, when he runs off with the youngest daughter, Lydia. But, what we’ll never forgive him for is driving a wedge between Elizabeth and Mr. Darcy. Fortunately, his lies, schemes and affairs are exposed when Elizabeth discovers that he’s what we’d call a deadbeat douchebag. Of course, in the end, this slippery guy kinda wins since Darcy pays for his wedding to Lydia. Ah well, at least he teaches us to beware the person who picks up your handkerchief – no matter how charming he may seem.

The villain in this loose Shakespeare adaptation, this high school model’s “game” is tested when the only thing he has to talk about is the Sears catalogue. Joey’s so self-absorbed that he thinks all he has to do is pay someone to take Kat Stratford to prom so her sister Bianca will go with him – as per their father’s rule. He is then SHOCKED when Bianca shows him that women are perfectly capable of making their own choices. And remember how we said he was self-absorbed? Even in the middle of a fight, Joey’s greatest concern is his upcoming modeling gig. P.S. we’re pretty sure his underwear and bathing suit poses are the same.

#6: Patrick ‘Pat’ Healy “There’s Something About Mary” (1998)

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More shallow than a puddle during the California draoght, Pat Healy is as sleezy as they come. He’s a private eye, whom Ted hires to track down his dream girl Mary. But Healy falls in lust at first sight and tries to convince nice guy Ted to stop pursuing Mary. Meanwhile, Healy himself stalks her and fabricates a new identity based on the information he’s learned to dupe her into falling in love with him… Because, y’know, being a greasy private investigator obsessed with breasts isn’t enough. And, as if his behavior towards women isn’t bad enough, he’s also awful with the differently abled. Healy treats humans like animals, and animals like he’s practicing to become an unlicensed veterinarian.

When “The Wedding Singer” starts, this douchebag’s already engaged to Julia, and to this day concerned viewers still aren’t sure why she agreed to this: he’s selfish, unkind and arrogant. What’s more, not only is Glenn cheating on Julia; he’s damn proud of it and has no plans to stop after the wedding. All that’s bad enough, but this popped collar, DeLorean-driving douchebag exhibits the true mark of a jerk at his “pre-bachelor party party,” when he sucker-punches the valiant Robbie in the face… Because violence will keep his relationship with Julia together, not – y’know – ditching the bimbos and going home to her… We hope no one ever has to grow old with this sleezeball.

Laundering money for drug dealers is bad enough; hiding that behavior from your friend-slash-colleague is despicable; having that friend-slash colleague murdered to cover up your mistake? Well that’s douche-tastic. Carl starts off as a normal, nice guy who seems like he’s there to comfort Molly after Sam’s untimely death – although he does seem a little too friendly. All the while he’s actually obsessively working behind her back to steal Sam’s passwords to get the money he needs to save his own skin. Eventually, Carl drops the façade, becoming physically and verbally aggressive and even threatening murder – all due to his fixation with power and money. Well, karma’s a bitch Carl – at least he won’t be haunting anyone ever again.

We can’t think of many things douchier than hiring assassins to kill your bride-to-be to start a war – well, except maybe planning to do it yourself on your wedding night. Prince Humperdinck is heir to the throne of Florin, and like many princely douchebags, he has others carry out his violent fantasies for him. Sure, he’s great at planning murders and getting other people to torture his enemies, but when faced with actual violence against his own person, we learn he has no backbone and is nothing more than a coward. Worse yet, he’s just got the kinda face you’d like to smack.

Overly protective, at times obnoxiously loud, and consistently inappropriate, this character fulfills an abundance of super-macho stereotypes. The kinda guy who’ll slam an opponent into the ground during a game of touch football – more than once! – or shoot a guy in the ass while hunting – and laugh about it! – his judgement is questionable. What’s even worse is that Sack has been unfaithful to his girlfriend Claire, something that John can’t just stand by and let happen – especially because of his feelings for her… Of course, when John tries to crash the couple’s engagement party, mister “propelled by pure testosterone” assaults the poor guy. Okay, we’ll just come out and say it: this lawsuit-waiting-to-happen makes the worst wedding guest ever. Before we unveil our top pick, here are a few honorable mentions: Phillip Stuckey “Pretty Woman” (1990) Daniel Cleaver “Bridget Jones’s Diary” (2001) Warner Huntington III “Legally Blonde” (2001)

#1: Cal Hockley “Titanic” (1997)

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We’re fairly certain the term “douchebag” didn’t exist in his day, but Cal Hockley may be the worst one in film history. At first he’s portrayed as simply controlling, but his elitism and greed really start to shine when Jack Dawson arrives and threatens his relationship with the beautiful Rose. This tuxedo-wearing egomaniac shows he has the unrestrained jealousy of a toddler when he destroys dinnerware, slaps his betrothed across the face and indiscriminately opens fire on a sinking ship. However, undoubtedly his biggest douche move – and the one that helps him survive the Titanic – is when embraces his true selfishness by stealing a child and pretending to be her father to secure a spot on a lifeboat. DOUCHE. Do you agree with our list? Which rom-com douchebag do you wish had made the list? For more entertaining top 10s published every day, be sure to subscribe to MsMojo.