The Greatest Virgins of All Time in Movies

Image via Complex Original

Played by: Molly Ringwald

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).

Well, with some movie magic, Mr. Big Shot actually does take notice of Samantha Baker (Molly Ringwald) on her sixteenth birthday and on the eve of that very special day, this young virgin is kissed by the man of her dreams.

And that's where John Hughes' '80s classic leaves it—Sam keeps it in her pants.

Played by: Anthony Michael Hall

Correction. Samantha does get noticed. But only by Ted (Anthony Michael Hall)-- the nerdy, freshman, underdog. Jake (Michael Schoeffling) might be the stud of Sixteen Candles, but it's actually Ted who truly mans-up and gets shit done. Who else would serenade his crush with "Hey Jude" at a high school party, try to come onto her twice and get rejected, then confess to her that he's a virgin, convince her to give up her panties to him so that he can brag to his fellow-geeks, show off the panties in the boy's bathroom, then give the panties to the stud and convince said stud to date Samantha Baker, drive the stud's car with the stud's girlfriend, and then lose his virginity to said girlfriend—or soon to be ex-girlfriend?

Only Ted.

Played by: Jesse Eisenberg

You would think that the prospect of losing his virginity to the pretty Sophie (played by Halley Feiffer) would relieve some of the stress brought on by his parent's divorce. Nope. Walt's neuroses are too deeply ingrained afters being raised by two writers.

He breaks up with Sophie during an argument about sex so that he can pursue the young student, Lily (Anna Paquin) living with Walt and his dad. No dice there. He accidentally gives her a nosebleed. And then the school realizes that Walt cheated during the talent show; he didn't write "Hey You." (Walt, 0; Roger Waters, 1.)

By the end of the movie he returns to one of his most memorable childhood memories: the squid and the whale exhibit at the Natural History Museum. Sometimes, losing your virginity isn't the key to all your answers. Maybe all it takes is a childhood memory. (But seriously, Walt, Sophie was a keeper.)

Played by: Emile Hirsch

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.

Somehow, the movie works, and avoids feeling like you're watching some teenage boy furiously type out a screenplay with one hand while masturbating with the other.

Played by: Natalie Portman

Talk about intense. In the passionate world of professional ballet dancers, Nina Sayers (Natalie Portman) struggles to make her mark. All she wants is to play the Swan Queen in Swan Lake. She's determined to outshine her rival Lily (Mila Kunis), whose dark, mysterious sexuality only enhances her abilities, making her appear effortless and graceful on stage.

Nina's also competing with Lily to win the approval of Thomas (Vincent Cassel), their instructor. And she can only do this by dancing the lead to the point of perfection. And thats how her journey to become the ideal Swan Queen begins. Her dance is her identity. It completely consumes her. But the role is demanding, challenging. She must face her alter-ego as she transforms from the white swan to the black swan. The white swan becomes a representation of her innocence, her virginity. The black swan becomes the symbol of her desire, her deepest, deadliest sexual fantasies.

However, that's enough literary analysis. The sex scene between Nina and Lily is unbelievable.

Played by: Alexandre Rodrigues

Rocket, the main character in the Brazilian crime drama City of God, takes his career as an aspiring photojournalist very seriously. He's caught quite literally in the middle of a gang war, and still he's snapping photos. In this favela, staying alive is more important than getting your rocks off, but only slightly. By the end of the movie, Rocket's career is taking off and a woman from the newspaper sees fit to pinch his v-card. Everything's coming up Rocket.

Played by: Kristen Stewart

Bella Swan is a walking PSA for abstinence 'til marriage. If you've watched Twilight, you know the whole series is about Bella losing her virginity, and being physically strong enough to handle Edward's sex drive. Trust. Besides running away from evil vampires and angry werewolves, all Bella and Edward do throughout the movies is debate whether or not they're ready to have sex. They eventually do, on their wedding night of course, and what results is a trashed hotel room with holes in the walls. "Sex is great if you wait!" The message couldn't have been more obvious.

Played by: Alicia Silverstone

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.

Murray (Donald Faison), Cher's best friend's boyfriend, has no problems whatsoever when it comes to popping her love-bubble delusions: "Yo look, are you bitches blind or something? Your man Christian is a cake boy. He's a disco-dancing, Oscar Wilde-reading, Streisand ticket-holding friend of Dorothy, know what I'm saying?" No worries—love eventually does catch up with Cher despite her cluelessness and like every chick-flick in history, the movie ends with a good make-out session...and a wedding.

Played by: Molly Ringwald

The princess, the good girl, the popular girl—that's Claire Standish (Molly Ringwald). It's no wonder that she ends up falling for Bender (Judd Nelson), the "criminal" with his bad-boy sex appeal and a knack bringing out the heat in everyone around him. From the moment they meet, its pretty obvious.

There's the scene where Bender leans over Claire's desk and looks straight into her eyes. "Have you ever kissed a boy on the mouth?" She's silent. "Have you ever been felt up?" Nothing. He continues. "Over the bra, Under the blouse, shoes off, hoping to god your parents don't walk in." She stares at him with wide eyes.

"Do you want me to puke?" she asks. The sexual tension is crystal clear. It basically continues for the rest of the movie. Loss of virginity is imminent and totally implied.

Played by: A.J. Cook, Hannah R. Hall, Leslie Hayman, Chelse Swain

The title spells out everything in Sofia Coppola's adaptation of Jeffrey Eugenides melancholy and hypnotic debut novel. The saddest fact about this movie (aside from the fact that all of the sisters kill themselves) is that all of the sisters (excluding Lux) die virgins. And here we were thinking that the boys would rescue the girls from the dreary suburbs and they'd all drive away on a beautiful, sun-soaked road. Looks like the sisters had other plans.

(But, you know, kudos to Lux for losing your virginity on a football field.)

Played by: Kyle Edwards

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.

Played by: Jennifer Jason Leigh

Fifteen-year-old Stacy has a rough go of it. Worried that she's not attractive or "experienced" enough to have a relationship with a guy, she makes some poor decisions. Like, having sex for the first time with a 26 year-old dude, at a place called "The Point." This then leads to her almost doing it with Rat, and then going all the way with Damone, which leads to her getting pregnant. Always remember, everyone: Wrap it up.

Played by: Anthony Michael Hall, Ilan Mitchell-Smith

What if your fantasy girl was real? Of course she'd be really, really hot. But what else? In this light-hearted '80s sci-fi classic, Gary (Anthony Michael Hall) and Wyatt (Ilan Mitchell-Smith) use a computer program to create their dream girl (Kelly LeBrock). Of course, nothing goes according to plan. Feelings, man. You never expect feelings.

Played by: John Hawkes

Mark O'Brien is the epitome of determination in the based-on-a-true-story The Sessions. Although he's paralyzed from the neck down as the result of polio, he still manages to lose his virginity to Cheryl Cohen-Greene (played by Helen Hunt), a sex surrogate.

Their relationship begins as a therapeutic thing, but soon blossoms into something romantic and real. It gives the film's ending a bittersweet feeling. We won't say anything more...

Played by: Anais Reboux and Roxane Mesquida

The hopeless virgin archetype gets turned on its head in Catherine Breillat's brilliant Fat Girl. Anais and older sister Elena have differing views on losing their virginity. The latter just wants to get it over with while the former wants to save herself for someone that loves her. Well, they both get their wish in the worst ways possible.

Elena meets a gross guy named Fernando, who pressures her into having sex with him while her sister listens. And then things take a strange and violent turn that reveals much about the treatment of sex in a patriarchal society. It also makes for one hell of a horror-story ending.

Played by: Emma Stone

Ask anybody: Chivalry is dead in your average, run-of-the-mill high school today. Gone are the days of asking a girl out on an innocent date with no sex involved. Let's get real. Nobody tries the old-school stuff anymore. It's mostly about hookups and friends-with-benefits and the next party where some shit might go down—if you're lucky.

And here and now, in the midst of this sex-craze, virgin Olive Penderghast (Emma Stone) must navigate her way through the highs and lows of the high school social scene. Olive's life changes when a small exaggeration about a weekend date turns into an explosive rumor that gives her the rep of being a promiscuous, badass bitch. Now she must deal with all the consequences of sex without actually ever having sex. But all hope is not lost! Olive's old crush, Todd (Penn Badgley), comes to rescue the damsel in distress by helping her tell the truth while giving her a taste of romance. Get it.

Played by: Jonah Hill and Michael Cera

This is definitely one of those it-all-happens-in-one-night and everything-that-could-possibly-go-wrong-does-go-wrong movies. Superbad follows two high-school losers, Seth (Jonah Hill) and Evan (Michael Cera). Seth is desperate to get laid and is convinced that he has a shot with his hip crush, Jules (Emma Stone). A night that begins with underage teens trying to buy alcohol turns into something epic. No, the two don't end up having sex that night but they do end up going on a double date the next morning. Sorry, guys. That's not exactly what y'all had in mind, is it?

Played by: Thomas Ian Nicholas, Chris Klein, Jason Biggs, Eddie Kaye Thomas

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.

Played by: Patrick Fugit

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.

Played by: Steve Carrell

Andy Stitzer (Steve Carell) embodies all things awkward, anti-social, and lame. He's that guy who doesn't know how to chill. It's hard to talk to him, even over a couple of beers after work.

But all of that changes after his co-workers discover that he is a virgin (who else would describe a breast as feeling like" a bag of sand"?). From then on it's a team effort to get Andy laid. In the supportive words of his friend Jay (Romany Malco): "From now on your dick is my dick."

And so Team Andy sets out to transform Andy into a regular dude, get him some game. He waxes his hairy chest and gets a lecture from Cal (Seth Rogan) on talking to women. He learns to act like a semi-douche and not act too interested in order to keep them interested. He's forced out there into the crazy, chaotic dating world that he so desperately wants to hide from. Really, he just wants to be himself and feels that this could actually be possible when he meets Trish Piedmont (Katherine Keener) and begins to develop a relationship with her. Don't worry—after some self-doubt, the usual couples' fight, a rad chase scene, and a good, old Hollywood kissing scene, the two end up marrying and Andy finally consummates his love. Boom.