Let's Talk About Sex, ONTD: 20 Movies About Losing Your Virginity

You never forget your first time, they say. And even if you were to try very hard to expunge the memory, Hollywood will do its best to keep on reminding you anyway. With seemingly another R-rated comedy released every week, (this week's being "The To Do List" starring Aubrey Plaza, opening this Friday, read our review here), The First Time has become increasingly well-trafficked territory, and it's not hard to see why. Really it's a screenwriter's dream—an (almost) universally relatable life-stage conundrum (in the Western world, anyway) that is ripe with potential for misunderstandings, social embarrassment and awkwardness, and that's just within the more comedic end of the spectrum.

In fact, it's telling that so many of the American films that deal with the subject do so from the vantage point of a "smutty" comedy (leaving stuff like "Kids" aside for a moment). Hollywood's double standard in regards to sex and violence is well documented, but it does seem kind of odd that you can go to the theater and see someone's viscera explode in 3-D pretty much as soon as your age is in double figures, but a naked breast or, God forbid, a penis...? But these films, in which there's often a lot of talking, planning, but not necessarily a great deal of skin bared, like their protagonists, get to walk the line between innocence and experience—they get to play in raunchy territory without necessarily falling foul of the censors. (Side question: is there any more prudish word in the world than "raunchy"?) On the flip side, though, the sex comedy will always try to test those boundaries and so, more than many genres, directly reflects the morals and mores of the times it's made in, which is why cherry-poppin' films made two decades ago can feel hopelessly dated. But again, that can be part of their charm.

Here are a few examples, ranging from the classic to the obscure, of the many, many times Hollywood has resigned its membership to the Big-V club, landed its first Martian probe on Venus, attended the Bush Inaugural Ball, or whatever other terrible euphemism you prefer, for the glorious rite of passage/horrible fumbling catastrophe that is having sexual intercourse for the very first time.

"American Pie" (1999)

One of the more unlikely franchises in recent memory (complete with a sub-franchise of seemingly endless direct-to-video sequels) began with 1999's "American Pie," a cheesy, warmhearted throwback to the sex comedies of the '80s (this time with 100% more Internet stripteases). It doesn't get more classic than this in terms of set-up: a group of four friends make a pact to lose their virginity by the time they graduate high school—by any means necessary. It's not as wacky or raunchy as its premise sounds, although this is a movie that earns its title thanks to an infamous scene involving Jason Biggs making sweet love to a freshly baked dessert. There's a sweetness to "American Pie" that sets it apart from some of the more soulless sex comedies of the past few decades, with characters you actually care about succeeding (scoring). The franchise has remained surprisingly chaste, right up until last year's "American Reunion," which still featured less sex than an average episode of "The Vampire Diaries." Times they are a-changin'.

"The 40-Year-Old Virgin" (2005)

Cementing the frat pack reign of Judd Apatow and raising Steve Carell to leading funnyman stature, "The 40 Year-Old Virgin" struck comedy gold. Andy Stitzer (Carell) is a middle-aged sales associate at a tech store who collects action figures and has yet to have sex (as you could guess from the title). It isn't a lifestyle choice, he's just stuck in arrested development: "You know what? I respect women! I love women! I respect them so much that I completely stay away from them!" Whereas other films on this list stray to either the more sentimental or crude side of losing your virginity, "The 40 Year-Old Virgin" manages a hilarious yet heartwarming balance (thanks to the co-writing efforts of Apatow and Carell along with some golden supporting cast improv), or as the trailer says, it's "A comedy that will touch you, like you've never been touched before." Rather than being creeped out by or blindly championing Andy, the audience actually feels for him and roots for him to be happy, which includes popping that cherry so he can have a "normal" adult relationship with Trish (Catherine Keener), the spacey young grandmother who would be his perfect other half. When Andy gets there and finally discovers, after all these years, what all the fuss has been about, well, who wouldn't break into a chorus or two of "The Age of Aquarius"?

"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.

"Cruel Intentions" (1999)

Based on the 18th-century French novel "Les Liaisons Dangereuses" by Pierre Choderlos de Laclos, "Cruel Intentions" uproots the story of social machinations and hypocrisy amongst the Ancien Regime and updates it to a high school set on the Upper East Side of Manhattan. At the center of the intrigue, grande dame Kathryn (Sarah Michelle Gellar) calculates the love lives and demises of her classmates with an icy, sadistic quality that would make Buffy bring out the trusty wooden stake. Kathryn herself is no virgin, but she manipulates her stepbrother and love interest Sebastian (Ryan Phillippe) into deflowering two women, the sheltered Cecile (Selma Blair) for revenge, and the upstanding Annette (Reese Witherspoon) for a sexual wager. Not that Sebastian is some wholly innocent pawn; he uses sexual and romantic blackmail to get his way. It is only when he falls for one of his victims that he gains some semblance of a conscience, although it's a bit too late in the game. Of course they each get their comeuppance, with Sebastian paying the ultimate price while Kathryn's dastardly ways are revealed by the virtuous (now virtue-less, in misogynist terms) Annette at his funeral by way of distributing photocopies of his very detailed and lurid diary amongst the student body. Suffering a ruination more damning than a calculated deflowering, Kathryn eats public humiliation while Annette drives away from it all with fond memories of Sebastian, ultimately not regretting her first time. The moral of the story is that sex isn't evil; it's the people who abuse and misuse it.

More movies about losing one's virginity at the ( SOURCE ).

Sex post, y'all!

Do you remember when you lost your virginity, ONTD? What was it like? Please do tell all the juicy deets... This gif of Chris Evans cumming his brains out demands it!
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