The best orgy-based comedy to come out in quite some time, A Good Old-Fashioned Orgy, will be available soon on Unrated DVD. But if you want awkward sex, the magical world of the movies has plenty of delightful options for you. It can range from funny to sad to just bizarre, but a good awkward sex scene sticks in your memory, probably forever. Here are some of the most awkward, intentional or otherwise

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Clark Griswold probably doesn't get to do it with his wife that often - after all, they are married. So when the opportunity presents itself, Sparky doesn't let the fact that they're crammed in a tiny sleeping bag with a feral mutt at their feet stop him. The result is one of the funniest awkward sex scenes around, although they admittedly don't get that far into the amorous process. Damn dog.

Pusher II

Tonny's been in jail for a while, and it hasn't exactly been good for his sex life. The possibly permanent brain damage he suffered at the hands of a friend he sent upriver isn't helping either. That becomes painfully clear in this harrowing scene, in which Tonny struggles dutifully to get it up in front of two prostitutes. It's a pretty tough scene to watch - in fact, "awkward" is probably an understatement.


Now would be a good time to draw an important distinction: Sex doesn't have to be bad to be reeaaaallllly awkward for the viewers at home. That's definitely the case with the sex scene starring master-of-the-high-kick-and-splits Jean-Claude Van Damme. There's just something incredibly wrong about watching the usually asexual JCVD do all these weird (and artfully lit) sexual acrobatics and tongue action. There's a Penn State joke to be made here, but I refuse to sink to that level.

Annie Hall

Sometimes sex is awkward due to psychological factors rather than physical ones. In a famous sex scene in Woody Allen's romantic comedy Annie Hall, the two participants (Woody and Diane Keaton) have out-of-body experiences, with their psyches getting up out of their bodies and walking around. Would it kill you to pay attention when you're having sex, people? Come on. Save the astral projections for when you're at church.

Lust, Caution

The sex in Ang Lee's spy thriller Lust, Caution is awkward because of what's happening out of the bedroom (she's a spy, he's a, um, spyee), but the contortionist-worthy sex scenes are pretty awkward by themselves. It might seem impossible that two people could twist themselves into such fleshy pretzels and still be able to breathe, but Tony Leung and Tang Wei somehow make it believable. Still pretty awkward, though, especially if you attempt any of that stuff at home.

American Pie

Here's another case of an awkward sexual encounter that was cruelly cut short by the hands of fate. Jason Biggs finally makes it into bed with Shannon Elizabeth, but before they can do anything, he, uh, experiences a premature disengagement of the landing gear, ifyouknowwhatImean. Not only that, it happens twice, which I thought was only possible if you're 13 years old and watching Cinemax.

Office Space

Nobody wants to think about their boss sleeping with their girlfriend, but Ron Livingston does exactly that in a nightmare sequence about his girlfriend Jennifer Aniston and his evil boss Gary Cole. The result is incredibly awkward, and since it's a nightmare, it doesn't even have to conform to reality. Cole's got his coffee mug in hand and uses the same obnoxious cadence he uses in the office. But just because it's not realistic doesn't mean it's not awkward (or horrifying). And who knows, maybe he really does have sex like that.

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