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Let’s Talk About Sex: 20 Movies About Losing Your Virginity

"Porky's," "American Pie" and more.

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.

Porky’s” (1982)
Arguably the “Citizen Kane” of teenage sex comedies, this is
the movie that inspired countless copycats and still remains a benchmark
of the smutty subgenre, as hilarious and risque as ever. It concerns a group of Florida teens hellbent on losing their virginity, who visit the titular establishment hoping a prostitute can help them
out. Instead, the redneck owners of the club humiliate the kids before
kicking them out, prompting a quest for revenge as the teens set out to get back at Porky and
his brother (who happens to be the sheriff). This thread of the
narrative is so painfully at odds with the central conceit of kids trying
to get laid that it oftentimes makes things feel forced and unnatural.
But there are enough shenanigans involving the horny young men and their
quest for sexual gratification to comfortably seat it in the
“stone cold classic” area of this particular list. And in fact some of its funnier moments can still feel somewhat shocking for their graphic-ness, like the famous sequence where the
boys are spying their female classmates through a hole they’ve
discovered in the girl’s locker room. They can glimpse a dozen or so
young girls, completely naked and proceed to get found out in the most vile way
possible (we don’t want to ruin it if you’ve been living in a cave for
the past 30 years). Safe to say, as a sex comedy, “Porky’s” has yet to be topped. And for good reason: it’s squealingly great.

The Sessions” (2012)
What makes “The Sessions“—which garnered a small amount of Oscar buzz last year but was ultimately drowned out by larger, flashier films and by Fox Searchlight‘s muddled, parallel awards campaign for “Hitchcock“—such a breath of fresh air in a somewhat stale genre, is that the virgin dying to lose “it” is a middle-aged man (the irrepressible John Hawkes) confined to an iron lung. His wish is to lose his virginity before he dies (his prognosis is grim), and he attempts this via the use of a sex surrogate, played fearlessly by Helen Hunt. The relationship between the iron lung-encased man and the surrogate, who tries to be all business but whose feelings do creep into the equation, serves as the emotional center for the movie, as well as the conduit through which such virginity loss hallmarks as premature ejaculation and full frontal (female) nudity, are trotted out. It’s a surprisingly winning combination of sentimentality and smut and the direction never veers too far in one direction or the other. It helps that it’s anchored by two of the finest performances ever to grace what is essentially a comedy about trying to get laid for the 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 Rules of Attraction” (2002)
Roger Avary said that with “The Rules of Attraction,”
he wanted a movie that was more representative of the typical college
experience. Instead of harmless japery and the gooey coming-of-age that
films like “American Pie” and “Sisterhood of the Travelling Pants
sell, “The Rules of Attraction” was supposed offer a glimpse into the
poisonous reality of American youth. It was a bold move and a tough sell
for Avary’s first post-“Pulp Fiction” directing gig (some eight years had elapsed), but the emotional vampires and drug-addled zombies who populate Bret Easton-Ellis‘ masterpiece of nihilism were more than up to the task. Few first-times can be as repulsive as that which Shannyn Sossamon‘s Lauren Hynde endures. Having fantasized for weeks about the possibility of an encounter with James Van Der Beek‘s
Sean Bateman, who she thinks is a charming stoner but who turns out to
be a borderline psychopathic coke-dealer, or with Victor, her absent
boyfriend and another grade-A bastard, she decides to just take the
leap. A student filmmaker catches her eye at a party, and, by this
point, so drunk she hardly knows what she is doing, they go off to a
bedroom to “smoke a joint.” She passes out, and when she comes to she
finds someone is having sex with her and her virginity is being lost. She
realizes that it is some drunk “townie” who she’s never met
and not even the film student, who is actually filming everything. She’s
horrified, and just as things can seemingly get no worse, the townie vomits
on her. It’s a horrendous, three-minute catalogue of degeneracy and
psychological catastrophe, and as a statement on America’s youth it
could hardly be more damning. No doubt a few of the “Dawson’s Creek” fans who
sat down to watch this rather mismarketed movie felt the same way.

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“?

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