25. Female Trouble (1974)
Dir: John Waters

In "Pink Flamingos," drag queen extraordinaire Divine had sex with her son, so when John Waters prepped his follow-up, 1974's "Female Trouble," he knew he'd have to come up with something really disturbing to top himself. And thus Divine does the impossible: she has sex with herself, as both halves of a typically Watersian tryst: female teen runaway Dawn Davenport and male sleazebag Earl Peterson. Earl picks up Dawn on the side of the road and forces her to have sex on a soiled mattress in a dump. Somewhere between the start of the sexual assault and the start of her pregnancy, Dawn begins to enjoy it. You can just imagine the delight Divine must have taken in informing anyone who told him to go fuck himself that he'd already tried that so they'd have to come up with something better. —Matt Singer

24. The Cooler (2003)
Dir: Wayne Kramer

Bad luck magnet Bernie (William H. Macy) dusts off a Sinatra LP to set the mood. "Luck Be a Lady" slinks out of the speakers until Bernie shuts the dresser drawer too hard, scratching up Frank's velvety pipes. This doesn't faze Natalie (Maria Bello) one bit, because she's the beautiful cocktail waitress who's going to turn nervous Bernie's life
around. And what better way to start than with a striptease! She shifts her hips, drops her shorts, and shakes the dice tattoo on her right ass cheek. Bernie's the winner. The scene works by highlighting the nervous fumbling and resultant humor that arises with first-time lovers. Bernie has trouble undoing her singlet, but after he succeeds, he climaxes in the blink of an eye. Natalie offers him forgiveness with ineffable grace, whispering those magical words, "You've got a great cock." That's what I call love. —R. Emmet Sweeney

23. Brokeback Mountain (2005)
Dir: Ang Lee

Sleeping bag sex is awkward in the best of times, so having your first homosexual experience in a two-man tent is really stacking the deck. But the thing that makes "Brokeback Mountain"'s key sex scene so effective is its utter lack of planning. Jack Twist (Jake Gyllenhaal) and Ennis (Heath Ledger) wind up huddled together for warmth -- the gold standard of come-ons -- and when Jack makes an awkward pass an angry, heated struggle ensues that morphs into some rough and urgent sex. Shot in almost complete darkness and lasting under a minute (!), the scene manages to subvert the tittering expectations of the viewing public and also offer a credibly awkward and confused rendering of how such a scenario might play out. Almost entirely dependent on sound, Ledger and Gyllenhaal make more of a couple of gasps and growls (along with a jangling belt buckle and twin zipper zips) than many sex scenes can do with mood music and the fully monty. —Michelle Orange

22. The Wayward Cloud (2005)
Dir: Tsai Ming-liang

The very first shot of Tsai Ming-liang's avant-musical pornocopia is a wide-lensed still of a sickly lit hallway; there's no music, no dialogue, and only two women passing each other over the span of a couple minutes. Yes, adventurous cinephiles often get gushy for this slow-burning Taiwanese talent, but his film's second shot could titillate and/or scandalize just about everyone: A nubile nurse (played by real-life Japanese sex starlet Sumomo Yozakura) lies spread-eagle on a white bed, naked from the waist down. It's a gorgeous but ridiculous image, as the only vibrant color is emanating from between her legs: a juicy, half-carved watermelon. Hsiao-Kang (Lee Kang-sheng), last seen selling watches on the streets in Tsai's pseudo-prequel "What Time Is It There?", would seem to have become Taipei's love doctor. He crawls toward the nurse's fruit, his tongue lapping at her seed, his prodding fingers getting stickier, the room filling with squishy noises -- wait, is there or isn't there a melon? After she comes, Hsiao-Kang sticks a vagina-sized chunk of drippy pulp in her mouth, a bright-pink money shot to the safest sex known to man... or horticulture. —Aaron Hillis

21. The Kiss (1896)
Dir: William Heise

The listing in the Edison films catalog reads "They get ready to kiss, begin to kiss and kiss and kiss and kiss in a way that brings down the house every time." Boy, do they ever. When May Irwin and John Rice reenacted an 18-second kiss (and kiss and kiss and kiss) from the end of the play "The Widow Jones" in early 1896, it hit the early film world with the force of a bomb. The popularity of the serial smooches (to say nothing of the ensuing scandal) ensured that the development of movies would forever be linked with the development of people getting it on in the movies. In some ways, these are the most important 50 feet of film ever printed. —M.S.

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