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Top 10 Sexual Extreme Movies

Some things to keep in mind about our list: To make the cut, the movies actually had to have some redeeming qualities. (So, sorry Boxing Helena!) We tried to pick movies that represented ten different extremes — after all, variety is the spice of (sex) life! And while some of the “extremes” in this list are indeed criminal, others are simply lifestyle choices. In no way do we mean to impugn the latter by including alongside the former.

Have fun walking on (the cliff-edge of) the wild side!

1. Secretary
Unlike 9 1/2 Weeks, this is the tale of a successful—and consensual—BDSM relationship. It’s really one of the only decent positive depictions of a dom/sub relationship in film. And despite the bondage gear and the spanking episodes and the power plays, it’s quite an adorable little love story. The fact that it’s feminist—Maggie Gyllenhaal’s character figures out what she wants and actively gets it—is just icing on the kinky cake! Secretary took home the Independent Spirit Award for best first screenplay and a Gotham Award for best breakthrough performance by Gyllenhaal.

2. 9 1/2 Weeks
In the sexual control freak category, there is of course the classic 9 1/2 Weeks. What starts off as a hot, experimental, Cosmo-inspired fling—fun with blindfolds and strawberries, private strip teases, playful cross-dressing, and public sex—ends as a toxic relationship about control, manipulation and degradation (and not the fun, consensual BDSM kind). It had a $17 million budget for director Adrian Lyne but only grossed $7 mil at the U.S. box office. At a pre-screening of 1000 people, only 40 people stuck around until the end, with 35 of those people saying they hated it. It was nominated for three Golden Raspberries, including worst actress. But — and this is a big “but” — it became a cult classic and, thanks to video sales, eventually grossed more than $100 million internationally. Even Roger Ebert gave it 3 1/2 stars for the believable chemistry between Kim Bassinger and Mickey Rourke. So while it’s a bit cliche by now, we feel we would have been remiss in our duties had we not included it in a Top 10 of sexual extremes.

3. Lolita (1962 and 1997)
First of all, if you have not read this book yet, don’t even think about watching these movie adaptations. In fact, don’t even think about finishing this Top 10—go download Nabokov’s 1955 novel for your Kindle or Nook right now and then come back. We’ll wait. Got it? Good. Now, without giving anything away, we can tell you that these two productions—the first by Stanley Kubrick and the second by Adrian Lyne—are two totally different stories, so different in fact, that it’s hard to believe they’re based on the same novel. Each is a vivid reflection of the time in which it was made, and what you could get away with cinematically (though Lyne’s much more blatantly erotic version still had a hard time finding an American distributor). The former is a goofy comedy-drama, the latter is all lyrical, dark and serious. (We’re partial to the 1997 version as a better—but still imperfect—representation of the novel.)

4. Shame
Starring Michael Fassbender and his penis, Shame is the least sexy movie about sex—because it’s not about desire, but about compulsion and unyielding need, which is rarely pretty (despite Fassbender’s perfectly toned abs and glutes). The movie wore it’s NC-17 rating with pride, and it worked: Shame became the second-highest grossing flick with that rating, just behind Showgirls.

5. Kissed
It’s a challenge to make necrophilia seem romantic and hot, but Canadian filmmaker Lynne Stopkewich kinda pulls it off in her adaptation of Barbara Gowdy’s awesome short story “We So Seldom Look on Love” (from her short story collection of the same name). The book gets away with more, but the movie holds it own thanks to Molly Parker’s creepy performance (Parker showed up later in a few episodes of Six Feet Under and in Dexter—guess she kinda has that death-obsessed look). Plus, it’s got the craziest money shot we’ve ever seen.

6. Spanking the Monkey (1994)
This is probably the closet thing you’ll ever get to a lighthearted film about incest, except for maybe The Hotel New Hampshire (but with that, the incest was just a side plot, so it doesn’t count). Still, Spanking is pretty dark which is to be expected when your main character ends up in a sexual relationship he’s not happy about with his own mother. (We mean, if he were happy about it, that’d be a whole ‘nother story.) It won the Audience Award at Sundance and the Independent Spirit Award for Best First Screenplay.

7. Crash
Not to be confused with the 2004 Academy Award winner for best picture about race relations in L.A. No, this ’90s movie, based J. G. Ballards’s 1973 novel of the same name, directed by David Cronenberg and starring James Spader and Holly Hunter, is all about symphorophilia: sexual arousal from staging and watching a disaster. In this case: car crashes. It received crazy mixed reviews: Roger Ebert gave it 4 out of 4 stars; we gave it a big goose egg for making soda come out our noses during the ridiculous sex scenes. Still, it won the Special Jury Prize at Cannes that year. Go figure.

8. Sick: The Life & Death of Bob Flanagan, Supermasochist
This is probably the least Sundance-y inclusion on our list (thanks to the nail-in-the-penis footage), and yet it was indeed a Sundance Film Festival documentary. In fact, it won a Special Jury Prize. Sick details Flanagan’s use of masochism not only for sexual gratification, but for regaining some control over his body, which was ravaged by—and ultimately defeated by—cystic fibrosis.

9. Breaking the Waves (1996)
Non-monogamy often gets a bad wrap, and Breaking the Waves doesn’t exactly reverse that trend. When a Norwegian oil-rig worker breaks his neck and loses his ability to perform sexually, he encourages his simple-minded wife to take new lovers and report back about her escapades. As her affairs grow more deviant and his recovery improves, she mistakes correlation for causation. Needless to say about a Lars von Trier film, it does not end well. Called one of the 10 best films of the 1990s by both Roger Ebert and Martin Scorsese.

10. Belle Du Jour (1967)
Catherine Deneuve, fabulously dressed in outfits designed by the then-little-known Yves St. Laurent, stars as an upper-class, Parisian housewife who can’t bring herself to have sex with her husband when he comes home at night—but fucking strangers for money at the local brothel in the afternoons seems to be no problem. (“Belle de jour” is the French term for a day lily, which only blooms during the day.) Some might think the story was boundary-pushing for its time, but get this: it’s based on a novel published in 1928! Directed by Luis Bunuel, promoted by Martin Scorsese for its 2002 DVD-release, and ranked #56 in Empire magazine’s list The 100 Best Films of World Cinema.

And while we’re talking about sex … read on for the most unrealistic sex scenes in the movies.