1. Parenthood (Joaquin Phoenix)
In the '80s, nobody talked about beating off; masturbation was something to accuse the creepiest, most maladjusted kids in school of practicing. In Parenthood, a young Joaquin Phoenix (credited as Leaf) nails the part. He sneaks out of his bedroom with a furtive look, a mysterious grocery bag under his arm, and a monosyllabic response to questioning. His mother (Dianne Wiest) is bewildered at his behavior, until she gets her hands on the bag and pulls out a copy of Wet, Wild and Ready (with "XXX" helpfully printed on the label). But leave it to the all-knowing Keanu Reeves to clear everything up: Phoenix has been masturbating, a lot. And that's okay. As Reeves tells Wiest—and the audience—"That's what little dudes do. We've all done it."
2. Spanking The Monkey (Jeremy Davies)
In his breakthrough role, Jeremy Davies bears a strong resemblance to elf/pirate pretty boy Orlando Bloom. But Spanking The Monkey shows why some young actors wind up in heartthrob roles opposite Keira Knightley, while others go on to play Charles Manson in a remake of Helter Skelter. The initially-fresh faced Davies comes home from college and winds up stuck for the summer with his ill, manipulative, sexually frank mother. Davies can't get to his internship, can't escape his parents' demands, and can't even get a little privacy to masturbate. Soon, he can't maintain a normal relationship with anybody, least of all his mother, who—in the film's infamous twist—has drunken intercourse with him.
3. The Exorcist (Linda Blair)
As Peter Biskind writes in Easy Riders, Raging Bulls, Linda Blair was 12 when director William Friedkin auditioned her for the part of the possessed girl in The Exorcist. When Blair explained that she knew what masturbation was ("It's like jerking off, isn't it?"), Friedkin asked if she ever did it herself. She answered, "Yeah, don't you?" Still, home rehearsals couldn't have prepared Blair for her big scene: Deep in the clutches of Satan, she effectively rapes herself with a crucifix, spraying blood all over her nightgown and screaming, "FUCK JESUS! FUCK YOU!" at the top of her voice. Then she jams her mother's face into the mess, screaming "LICK IT!" before casting her aside. "Do you know what your cunting daughter did?" asks Satan/Blair. Yeah, well, it was pretty hard to miss.
4. The Squid And The Whale (Owen Kline)
Owen Kline is the younger of two sons of stuffy Park Slope, Brooklyn writers Jeff Daniels and Laura Linney. When his parents separate, Kline finds several ways to cope—and the creepiest comes in the school library, when the sight of a girl with giant bright earrings prompts him to walk over to the stacks with a wrinkled piece of porn and rub himself off against a bookcase; after he ejaculates, he smears his semen along the spine of some books. Later, Kline declares that he's a "philistine" who hates "books and things," by way of rejecting his father's book-based authority and his mother's literary success. Maybe his handling of the library books is another way of acting out against them. Or maybe that's just how writers breed in Park Slope.
5. Junebug (Amy Adams)
Amy Adams loves Ben McKenzie. They're married; she's carrying his child. But McKenzie is withdrawn and uncommitted. In one scene in the middle of the film, Adams, lying in bed hugely pregnant, comforts herself with a photo of the two of them together, though in the photo, McKenzie looks just as distant as in life. Meanwhile, her husband's in the other room complaining about their marriage, which she can hear through the walls. "I woulda gone to Washington D.C. in 12th grade, except for her!" is the last thing she hears before she finishes.
6. Shortbus (Paul Dawson)
In Shortbus, the graphic sex serves the plot and the character development. But no matter how mature viewers feel coming into the movie, there's no getting around the curiosity factor in the opening sequence, as a buck-naked Paul Dawson gets on his back, flips his feet over his head, and tries to fellate himself. He gets excruciatingly close and manages a slight insertion before he ejaculates—and then bursts into tears. Minutes later, his lover comes home, and Dawson quickly gets dressed and runs away, while everyone in the theater silently ticks his acrobatic act off their "things to see before I die" lists.
7. Your Friends & Neighbors (Aaron Eckhart)
The arch metropolitan elites of Your Friends & Neighbors can't satisfy each other, sexually or otherwise. Aaron Eckhart plays the schlubbiest character, which is almost to say, the most likeable one. Discussing his best sexual experience, Eckhart brags, "The best lay I've ever had? That's easy, it's me!" Nothing satisfies him like himself, and he enjoys a post-coital spank better than the real act with his wife (played by Amy Brenneman). But even though he's the one character not dependent on other losers for his own satisfaction, Eckhart gets dumped anyway: While his wife beds down unhappily with the menacing Jason Patric, Eckhart tries but fails to reach orgasm on a sex chat line. In narcissistic despair, he shouts, "What is the matter! Is it me?"
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8. Happiness (Rufus Read)
In another grim late-'90s indie flick, Happiness, writer-director Todd Solondz suggests that the only true happiness comes at orgasm. Young Rufus Read, whose family has had a really, really rough year, wants to masturbate, but his efforts fail until the end of the film, when the sight of a blonde in a bikini finally brings him to finish. He ejaculates on the balcony railing, and in one of the film's only bursts of comic relief, the family dog licks it up, then runs back inside to lick Read's mother (Cynthia Stevenson) square on the kisser. Read follows him in and announces to his whole family, "I came!" Finally, he's happy—fleetingly—and the family has a great story to tell at Thanksgiving get-togethers.
9. Mulholland Dr. (Naomi Watts)
David Lynch's thriller Mulholland Dr. can be broken into two halves—the "fantasy" section, followed by the shorter "reality" section, which kicks off when Naomi Watts' fresh-faced naïveté collapses into a haggard expression, haunted eyes, and a hint of a snaggletooth. But nothing in that section looks as real as Watts masturbating on the couch, sweating and struggling and coming to tears at her inability to climax. The blurred shots of the wall across the room have been interpreted as her attempt to disappear into fantasy, only to crash right back into real life. Watts has described her character as "full of self-loathing," and said that "I kept on weeping and falling to pieces, because I just felt so embarrassed and humiliated."
10. American Beauty (Kevin Spacey)
Kevin Spacey opens American Beauty in the shower, explaining that his few moments alone with himself will be "the high point of the day." Masturbation sums up the death-like routine of his suburban life, but later in the film, it's the turning point: Smitten with his daughter's high-school friend, he starts to pleasure himself in bed while a comically frigid Annette Bening sleeps beside him. (Still a wimp, Spacey timidly fantasizes that he's pleasuring the girl, and not the other way around.) When the rapid thumping motion wakes Bening, they get into a fight, and Spacey finally declares his independence—even throwing her threat of a divorce back in her face. Says Spacey, "It's a great thing when you realize you still have the ability to surprise yourself"—especially when it comes from something you've been doing since you were 13.
Side note: Alan Ball's Six Feet Under uses the same gesture in the third season, when Peter Krause, stalling for time on his way home to a loveless marriage, pulls over and masturbates in his car. And just as in American Beauty, the writers couldn't find a way to fix the marriage without offing one of the spouses.
11. Babel (Boubker Ait El Caid)
At the beginning of Babel, a young Moroccan boy—after looking at his sister, naked, through a hole in the wall of her hut—takes a break from herding goats to drop trou and masturbate. However, his brother interrupts him by taking potshots at coyotes with their brand-new rifle, and that leads to a shooting contest between the brothers—which only stops after they wound an American tourist (Cate Blanchett) on a tour bus. Had the boy not been interrupted, Blanchett might never have done a bedpan scene, Gael García Bernal couldn't have shown us the best way to twist the head off a rooster, and Rinko Kikuchi would've gotten a lot less naked. In other words, had the kid gotten off, the whole movie could have been avoided.
12. Little Children (Gregg Edelman, Jackie Earle Haley)
As a bored, overeducated suburban housewife, Kate Winslet is an easy mark for an adulterous affair. But to keep viewers sympathetic to her needs, Little Children writes off her husband, Gregg Edelman, as a total drip. The pale, cave-bug-like Edelman can't stop surfing an amateur sex site run by "Slutty Kay." His obsession grows until Winslet walks in on him at his computer, masturbating to Kay with her mail-order panties stretched like a mask across his face, making him look like a polka-dotted gynecologist. After that, Winslet feels a lot less guilty about messing around behind his back.
A more horrifying scene comes later in the film, when Jackie Earle Haley—a sex offender who served time for indecent exposure—takes unlucky date Jane Adams to dinner. When she drives him home, he asks her to pull over and kill the lights. As she tells him how bad her last date was, she notices a strange sound and looks over to see him masturbating and gazing at her like a snake, hissing, "You better not tell on me… or I'll fucking get you." A swing-set in the background completes the film's most disturbing moment.
13. Bad Lieutenant (Harvey Keitel)
Of course, Harvey Keitel perfected the "jerking off in front of girls trapped in a car" scene in Bad Lieutenant, when he catches two young Jersey girls on the town without their licenses and threatens to tell their father unless they do what he says. Keitel's abuse of his authority, crossed with the pathetic sight of him playing with himself as the girls humiliate themselves in sexual poses, gruesomely proves the depth of his corruption.
14. Fast Times At Ridgemont High (Judge Reinhold)
There's no worse nightmare than coming back from your fast-food job, still wearing your sweaty pirate uniform, and getting caught in the bathroom by the girl you're fantasizing about. Still, Reinhold plays this legendary caught-in-the-act scene for laughs, and 30 years' worth of guys have staged their own run-throughs thanks to the vivid shots of Phoebe Cates striding across a misty swimming pool and unsnapping her bikini top. After she finds him, Cates cringes away—but Reinhold wins the round with an exasperated, "Doesn't anybody fucking knock anymore?" Nice save, dude!