20. Damage (1992)

God bless Juliette Binoche and Jeremy Irons. We’ve never seen a movie where either one of them does less than go for broke. Unfortunately, in Damage , "go for broke" seems to mean "share a nice, romantic . . . seizure." Hey, we’re all sex enthusiasts here, but this just looks more spastic than fun. — Peter Smith

19. Monster’s Ball (2001)

Halle Berry won a Best Actress Oscar for her performance as the heartsick Leticia to Billy Bob Thornton’s equally wounded Hank, and you have to wonder if this raw sex scene didn’t give her the golden edge. Fucking Thornton while repeatedly braying “make me feel good” is better than ten Charlize Theron fatsuits-cum-mullets, any day. Whether you find the grief-filled Southern Gothic plot to be ultimately uplifting, or worthy of a boycott, she justifiably received much praise for her bravery in letting go of the pretty, and making this scene pretty ugly. Here, the two characters learn to feel again via fucking — but what’s good for their souls isn’t a joy to watch. Yes, Berry’s gorgeous breasts, ass, and everything in between receive plenty of screen time, but that’s part of the problem. You know at that moment you’re just watching a beautiful movie star fuck a not-beautiful star. Or, if still enthralled in the plot, you can’t escape the fact that it’s sad, desperate sex on a bad couch in a bad place between two broken people. Artistic shots of a caged bird notwithstanding, this is sex that makes you cringe, for multiple reasons. — Nicole Ankowski

18. In the Cut (2003)

In the Cut tried so desperately to be dark, sexy and dangerous that the overall effect is like watching Britney Spears attempt to seduce you: cringe-worthy. Meg Ryan (and her freshly enhanced lips) wanted to break free from their good-girl image by playing repressed English professor Frannie, who witnesses a blowjob, becomes embroiled in some mysterious neighborhood murders, and begins a voyage of sexual awakening. Mark Ruffalo and his freshly enhanced mustache play Detective Malloy, the lead investigator who may or may not be the killer. Here Frannie masturbates face-down in bed, while Malloy (and his ‘stache) watch intensely, smoking and leaning in out and out of the dark, sexy shadows. It’s as bad as the final sex scene, in which Frannie handcuffs a seated Malloy to a radiator, then rides the hell out of him while he urges her to “fuck herself” over and over. After all the hype of Ryan’s sex scenes, the hopes for Jane Campion’s feminist sex film, and the silicone lips, the end result is we just want to tell everyone responsible for the film to do exactly as Malloy said. — Nicole Ankowski

17. The Life of David Gale (2003)

This boneheaded message movie is simply overflowing with moments that are just plain wrong – so much so that it offers two icky sex scenes for the price of one, both of which are repulsive for reasons other than the prospect of Kevin Spacey flesh on display. Sure, that’s reason enough, and the first one — in which Spacey’s anti-capital punishment professor David Gale gets jiggy with a student on a bathroom sink — does offer an unwelcome view of Spacey’s rear flank in full heave. If he’s such a smart fella, he probably should have figured out she was only upset about her grade and planning to frame him for rape. But he’s not such a smart fella after all, as we learn when Gale is sitting on death row, giving his last interview to "Mike Wallace with PMS" reporter Bitsey Bloom (Kate Winslet, thankfully spared any Spacey coitus). The details of his plan to be executed by the state of Texas in order to prove a point are too ludicrous to recount in full, but suffice it to say the scheme involves intercourse with a dying Laura Linney, who is later found naked on the kitchen floor, bound and gagged with a plastic bag over her head. Next time, Kevin, just send flowers. — Scott Von Doviak

16. 9 Songs (2004)

Director Michael Winterbottom’s attempt to extend the boundaries of on-screen eroticism chronicles the affair of glaciologist Matt (Kieran O’Brien) and Lisa (Margo Stilley), an American college student visiting London. The movie, which includes unsimulated scenes of intercourse, oral sex and masturbation, basically consists of seventy minutes of the two leads banging away at each other, alternating with concert footage of such bands as Primal Scream, Franz Ferdinand, and the Dandy Warhols, with our heroes in the audience.

Winterbottom wanted to make a love story about two people whose primary connection to each other was sex (and, apparently, their fervent support of live music), and he wound up proving that even real sex can be boring if you have no reason to care about the people engaged in it, especially if the lighting and editing are overly mannered and rock groups keep popping up as a form of noisy coitus interruptus.

Stilley, a model making her acting debut, is much the livelier of the two (although she really needs to eat a sandwich). After awhile–say, around the time she tells her lover that sometimes, when they kiss, she’d like to bite his lip, "and not in a nice way" — she looks as if she were trying to wake up her co-star, and by the end it’s begun to seem as if her character is a little nuts, which may or may not have been intentional. As for O’Brien, he narrates the film while remembering the affair after he’s gone to work in the Antarctic, which seems like a waste of plane fare; if he wanted to study big blocks of ice, he could just look in the mirror. — Phil Nugent