Superbad Emma Stone

"Superbad" (2007)
As far as adolescent obsessions go, "Superbad" is concerned more obviously with booze, but that's not to say that getting their ends away isn't a major factor driving Seth and Evan (and, to a lesser extent, their friend Fogel) in Greg Mottola's already-seminal teen comedy "Superbad." They might not come out and out and say it, but there can be little doubt that these kids are virgins: anyone who was once a teen boy, and ever went to ridiculous lengths to chase the vaguest possibility of sex, can identify with the idea that the pair will face armed robbery, immature cops and coked-out weirdos for the chance to pop their cherries with Martha MacIsaac and Emma Stone. In fact, it's only Christopher Mintz-Plasse's Fogel that succeeds: his reputation as "McLovin" sees him bed a girl at a party by the film's end. In part, it's because unlike Seth and Evan, he isn't totally terrified of women—Michael Cera's Evan is like a rabbit-in-the-headlights when he discovers that sweet girl-next-door Becca is at least as horny as he is, while Jonah Hill's Seth struggles to come to terms with the idea that Jules might be more attracted to him sober than drunk. But, their humiliations over, Mottola wraps up the film with the hope that the pair might have learned from their experiences, and are ready to get laid not with hopeless objects of their fantasies, but with real women.

The Girl Next Door

"The Girl Next Door" (2004)
Based on every teenage boy's wet dream, "The Girl Next Door" is about a porn star Daniele (Elisha Cuthbert) moving in next door to straight-laced high school senior Matthew Kidman (Emile Hirsch), who recently earned a college scholarship for "moral fiber." At first, he just thinks the titular girl next door is just a very attractive neighbor who's miraculously into him. When his friend Eli (Chris Marquette) stumbles onto one of her films, Matthew grapples with continuing to date a porn star, which isn't helped by Eli's goading, "What would JFK do? You know he'd tap that ass." After some ups and downs and some run-ins with people from Daniele's past, Matthew ends up taking her to prom,  along with a few of her colleagues, to the dropping jaws of his high school student body and chaperones. And the evening culminates in the two having sex in the back of their prom night limo. Generally disdained by critics for somewhat obvious reasons (Roger Ebert called it "a nasty piece of business"), "The Girl Next Door" may not be a cinematic classic, but it meets most expectations, the good and the bad. Also, keep an eye out for a pre-"There Will Be Blood" Paul Dano.

Sex Drive

"Sex Drive" (2008)
One of the more blatant "let's pop our cherry" movies on this list, "Sex Drive" is all that you'd expect and more, definitely not for the faint of heart or the shy of crude, gross-out humor (it makes Adam Sandler look like Woody Allen). Bullied relentlessly by his homophobic douchebag brother (James Marsden, surprisingly), awkward 18-year-old Ian Lafferty (Josh Zuckerman) is generally unlucky with the ladies, resorting to chatting online under a heavily-photoshopped avatar and "taking advice" from his Jean-Claude Van Damme poster (they do realize this is 2008, right?). After failing to move out of the friend zone with Felicia (Amanda Crew) at a typical movie high school party (booze, no chaperones, etc.), Ian decides to drive from Chicago to Knoxville to lose his virginity to the girl he met online, who goes by the screenname of "Ms_Tasty" (not quite Carlos Danger, but still up there in cheesiness). With Felicia and his other buddy Lance (Clark Duke) by his side, Ian takes his brother's 1969 Pontiac GTO Judge out on the open road and they meet a few characters along the way including a passing pissing hitchhiker (a very brief and wasted David Koechner appearance) and a cursing, sarcastic Amish man (Seth Green, one of the very few highlights). Surprisingly, Ian actually gets to meet Ms. Tasty and she's a real girl (Katrina Bowden) after all, albeit already attached to a bearded carjacking boyfriend (Andrew Sheridan). Following typical coming-of-age stories, Ian does succeed and lose his virginity, just not the way he imagined (though you'll see it coming from 540 miles away).

Easy A

"Easy A" (2010)
Another movie to analyze teen sexuality from the female perspective is director Will Gluck's "Easy A," a modernization of the high school curriculum must-read "The Scarlet Letter" about gender discrimination, and those good ol' double standards when it comes to men and women and their attitudes to sexual reputation. High schooler Olive Penderghast (Emma Stone) helps out a friend by saying the two had sex, which blossoms into Olive lying about being "a slut" in order to gain popularity and gifts. As she succinctly sums up: "That's the beauty of being a girl in high school; people heard you had sex once and BAM—you're a bimbo." "Easy A" shows the unfair and downright disturbing treatment of young girls in high school—albeit with a cheeky script and a hilarious performance by Stone. The mere mention of sexuality causes Olive to be adored and sought out by countless guys, ones who know her secret, mind you, and when she ends up needing help to prove she isn't promiscuous, the guys want to protect their invisible credibility. The plot doesn't go as dark as it could—Olive goes out with a supposedly good guy who really does want her to put out, only to have her get away from him safely—but it casts an eye on a topic that's still reinforced in movies today; that women cannot be sexual for fear of being cast out and scorned. Thankfully there's a lot of funny to wash down the medicine with. 

Almost Famous

"Almost Famous" (2000)
Although shedding his virginity was not a set goal for this precocious lead (unlike many on this list), we still consider the coming-of-age meets rock history story "Almost Famous" as a "losing it" film. Based on writer-director Cameron Crowe's own stint as a Rolling Stone correspondent, William Miller (Patrick Fugit) sets out to be a proper music journalist and winds up following Stillwater (loosely based off of an amalgam of bands including Led Zeppelin and Lynyrd Skynyrd) thanks to "Band-aid" groupies. William falls for the head groupie, Penny Lane (Kate Hudson in a career-making role), but unfortunately, she's already taken/claimed by guitarist Russell Hammond (Billy Crudup). Having been friend-zoned (including daydreamy talks of running off to Morocco), William hooks up with a few of the other groupies (the specifics are a bit hazy as you'd expect from the era), but still loves Penny as deeply as any first love. Even after she leaves the tour due to a combination of quaaludes and Russell's wife, William still holds on to that torch. Although the other girls may have popped his cherry, Penny will always be the ultimate "girl who got away."