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The Greatest Movie Virgins of All Time

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Over the weekend, Aubrey Plaza's The To-Do Listhad the largest opening of any specialty feature this summer, reinforcing a truth as old as time: We like to cheer for people questing to lose their virginity. The movies have been telling these tales since the censorship codes first slackened. It's great to see The To-Do List succeed, as more often than not, these films follow young men. But, as we know, everybody wants to get laid.

Especially these classic movie characters—here are the Greatest Virgins of All Time in Movies.




Samantha Baker in Sixteen Candles (1984)

She’s that cute redhead, the nice girl that nobody notices in class or in the hallways. And obviously, she has a crush on the high school jock (you know, that athletic, broad-shouldered guy with a sweet car and a blonde, somewhat ditzy girlfriend that almost every other guy would like to punch in the face but can’t because this guy could probably win any fight without even trying, hands down).



Matthew Kidman in The Girl Next Door (2004)

Matthew Kidman's less-than-memorable senior year takes a turn for the better when porn star Danielle (played by Elisha Cuthbert) moves in next door. Sure, Matthew gets into some interesting scenarios (giving a speech while high on ecstasy, essentially directing a sex ed tape) but it ultimately leads to him losing his virginity with Danielle in a limo. By the end of the movie he's able to go to the college of his dreams, and take Danielle with him.



DJ Qualls in Road Trip (2000)

Kyle gets shoveled most of the crap throughout Road Trip. He gets made fun incessantly, has a controlling father, gets his car destroyed and (unknowingly) has his French toast tainted by some unpleasant extra ingredients. But it's all worth it for Kyle: While on the road to Austin with the boys he outdances everybody to Run-D.M.C.'s "It's Tricky," and loses his virginity to Rhonda (played by the late Mia Amber Davis). "I had sex last night...with a girl," Kyle triumphantly tells a nurse when the gang wants to give up some sperm for money. We're proud of you, Kyle.



Cher Horowitz in Clueless (1995)

This is that virgin who falls for the good-looking, well-dressed, somewhat in-the-closet, gay guy and tries to get with him...rather unsuccessfully. Cher Horowitz (Alicia Silverstone) is mystified when it comes to relationships, love, and sex in this classic, a very '90s adaptation of Jane Austen's Emma.



Kevin Myers, Chris "Oz" Ostreicher, Jim Levenstein, and Paul Finch in American Pie (1999)

You know how the story goes: four seniors in high school make a pact to lose their virginity before graduation. But it's definitely easier said than done: Jim Levenstein (Jason Biggs) takes Oz's (Chris Klein) description of sex too seriously (eating pie is so passe); Finch ( Eddie Kaye Thomas) practically becomes dateless after being a part of an embarrassing prank by Stifler (Seann William Scott)—R.I.P. the girl's bathroom—and the rest of the guys, well, their situations are only slightly less embarrassing. Ultimately, the gang ends up fulfilling the pact, and go on to graduate de-virginized. Too bad we can't say the same for Chuck Sherman (Chris Owen). He'll have to live with peeing on himself at prom for the rest of his life.



William Miller in Almost Famous (2000)

Imagine being a high school teenager with dreams of being a rock journalist. You're something of a geek, but in an adorable way. And then—turn up—you get the opportunity to write a big cover story for Rolling Stone. Not only do you get to live life like a rock star, but you're writing for one of the biggest music publications in the world.

Well, that's William Miller. He goes on the road, watches rock stars trip on LSD, and, most importantly, loses his virginity to a gang of gentle groupies. Lucky bastard.


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