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The Biggest Movie Losers to Ever Get the Girl

Hollywood screenwriters love nothing more than movies that end with the shlubby guy landing the girl of his dreams. Maybe it’s their way of getting back at the popular girls who dissed them in high school. Maybe they actually believed it when their moms told them it’s what inside that counts. Whatever the reason, movie losers score way out of their leagues far more often than their real-life counterparts. In an effort to bring you back to reality, here’s a list of big screen pairings that would never happen in reality. Consider it a public service.

helms-hangover-125.jpg Ed Helms, The Hangover (2009)
Ed Helms is well …  Ed Helms. Heather Graham, on the other hand, is a total looker! So when she goes all googly-eyed for Helm’s pasty dentist Stu, his friends can’t believe it, he can’t believe it, and you certainly shouldn’t believe it either. Helms is the nerdiest guy in a group of friends who aren’t exactly the Rat Pack, he spends half his time on the phone with his girlfriend, and yet he ends up with the best looking girl around, just, you know, by chance. Nobody ever gets that lucky in Vegas.

Seth Rogen, Knocked Up (2007)
Pregnant or not, Alison (Katherine Heigl) is hot and Ben is not. Judd Apatow continues to try to persuade the world that any loser guy can get any hot girl at any time he chooses — don’t buy it!  No amount of booze makes sense of the fact that Alison ever gives Ben the time of day in the first place. The fact that she ends up staying with him in the end — well, she can always blame it on the hormones.


Steve Carell, The 40 Year Old Virgin (2005)
His virginity doesn’t matter as much as the fact that he’s a dorky middle-aged
stock-room employee at a Best Buy clone with social skills that are
limited at best. Trish (Catherine Keener), your classic hot mom, could do better. Carell’s Andy doesn’t know how to make small talk with other men, let alone women, and lest you forget crucial details, he has an
extensive collection of action figures and a framed Asia poster in his crib. Well,
at least you know why he was a virgin for so long.


John Cusack, High Fidelity (2000)
Who’s the perfect match for Laura (Iben Hjejle), a smart, attractive, and successful lawyer? According to High Fidelity, it’s a middle-aged man-child who owns a failing record store, obsessively talks music with the two losers he employs, and for good measure, finds the time to cheat on her when possible. Even Rob himself is confused by this, asking, “How does an average guy like me become the number one lover?” If he doesn’t get it, perhaps you shouldn’t even bother trying.


Matthew Perry, The Whole Nine Yards (2000)
Sorry, Chandler: In
reality, there probably aren’t a ton of couples composed of broke,
nerdy dentists and buxom mafia wives. But that doesn’t stop Perry from
seducing mafia babe Cynthia (Natasha Henstridge). Tony Soprano, Michael
Corleone… Those are the kind of guys connected women desire.
An anxiety-ridden married dentist who’s controlled by his wife and
mother-in-law in no way fits the job description.


Leonardo DiCaprio, Titanic (1997)
Yeah yeah, it’s a beautiful love story. Two people from starkly different backgrounds fall in love — and look where it gets both poor, dirty Jack and his rich, princess-y soul mate Rose (Kate Winslet). He dies a horrible death by drowning and she spends her life miserable because he’s died a horrible death. Come to think of it, this one’s actually a cautionary tale.


Ralph Macchio, The Karate Kid (1984)
review the case of Daniel-San. He’s new in town. His only friend is a
middle-aged Japanese man. His Mom has to drive him everywhere and he
doesn’t appear to have any money. He has bad Chachi hair. To fresh-faced young Ali (Elisabeth Shue),
this apparently makes him irresistible, much more so than than her
rich, popular, karate-champ boyfriend Johnny Lawrence (Billy Zabka). Glory of love, indeed.


Anthony Michael Hall, Sixteen Candles (1984)
Hall’s character in this ’80s classic doesn’t even have a name; he’s credited simply as “The Geek”! He’s also a freshman, which is so not a positive quality for a dude to
have, and he’s the kind of guy that sells pervy photos in order to acquire floppy disks.
Despite these deal-breakers, the prom queen (Haviland Morris)
just can’t get enough. In fact, when her boyfriend leaves
her for Molly Ringwald she happily accepts The Geek as a consolation
prize. As if.


Woody Allen, Annie Hall (1977)
It may not be built to last, but the fact that Alvy (Woody Allen)’s relationship with the vivacious Annie Hall (Diane Keaton) happens at all is a minor miracle. Alvy, after all, is neurotic, annoying, and no Zac Efron. Annie is a tie-wearing, free-thinking hottie who’s also a talented artist and photographer in her own right. Why she would spend years with the perpetually miserable Alvy is a mystery for the ages.


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