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Countdown: The most embarrassing sex scenes on film

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Steve Carell, The 40 Year-Old Virgin

Countdown: The most embarrassing sex scenes on film

As Woody Allen said, sex is dirty only if you do it right. If you do it wrong, however, it’s pretty funny.

Should The 40 Year-Old Virgin (opening Aug. 19) join Wedding Crashers on the list of raunchy comedy hits, we could be seeing a lot more hilariously embarrassing movie sex scenes, like the one shown above, where Andy Stitzer (Steve Carell) accidentally kicks his date out of bed. The film is the latest in a line of comedies that present sex not as a gauzily lit event that finds the man and the woman harmoniously in sync, but rather as an activity that’s fumbling, awkward, unsatisfying, and above all, humiliating.

On the following pages, we’ve listed the most embarrassing sex scenes in movies. To keep the list honest, we’ve left off solo performances (out goes Ben Stiller’s ”hair gel” moment in There’s Something About Mary) and encounters between people and foodstuffs (out go Jason Biggs’ liaison with a pastry in American Pie and Meg Ryan’s apparently pastrami-induced orgasm in When Harry Met Sally…). The 10 sex scenes remaining in our Hall of Shame are the ones that made us laugh and wince the most for the way they humiliated the characters — and sometimes the actors.

Emma Thompson, Jeff Goldblum, ...

The Tall Guy

(1989)

Embarrassing sex in ”The Tall Guy”

THE CHARACTERS Dexter King (Jeff Goldblum, right), an American stage actor in London, and Kate Lemmon (Emma Thompson, left), a no-nonsense nurse

THE SCENE Dexter and Kate’s first date ends with what may be the most painful-looking sex scene ever filmed, a room-destroying romp that involves the acrobatic lovers crashing into every available surface.

EMBARRASSMENT QUOTIENT Modest, especially compared to Dexter’s leading role in a hilariously bad, Andrew Lloyd Webber-ish musical about the Elephant Man. If anything, the scene was probably less embarrassing for the characters than for Goldblum and Thompson, who never did anything this racy before and haven’t since.

EW MOVIE GRADE B-

Tom Hulce, National Lampoon's Animal House

National Lampoon’s Animal House

(1978)

Embarrassing sex in ”National Lampoon’s Animal House”

THE CHARACTERS Delta fraternity pledge Larry ”Pinto” Kroger (Tom Hulce, above), and Clorette DePasto (Sarah Holcomb), a grocery store cashier and daughter of the mayor

THE SCENE After Pinto unsuccessfully tries to take off Clorette’s bra during a makeout session, the girl finally removes it herself — then immediately passes out, leaving a surprised Pinto holding great handfuls of tissue. His good and evil sides debate over whether to take advantage of the unconscious Clorette. In the end, he dumps her in a shopping cart and drops her off at her father’s doorstep.

EMBARRASSMENT QUOTIENT Moderate compared to a later scene, when Clorette reveals to Pinto that she’s underage, then introduces him to her father as ”the boy who molested me.”

EW MOVIE GRADE B+

The Ice Storm

The Ice Storm

(1997)

Embarrassing sex in ”The Ice Storm”

THE CHARACTERS Wendy Hood (Christina Ricci, left), a suburban Connecticut teen in 1973, and Mikey Carver (Elijah Wood, right), her neighbor and schoolmate

THE SCENE The bored teens, hanging out in Mikey’s living room, engage in some heavy petting, an activity made kinkier by the fact that Wendy’s wearing a latex Halloween mask of Richard Nixon.

EMBARRASSMENT QUOTIENT Modest for the teens, who are startled mid-grope when Wendy’s dad, Ben (Kevin Kline), walks in on them. Much more humiliating for Ben, who’s having an affair with Mikey’s mom, Janey (Sigourney Weaver).

EW MOVIE GRADE B+

Eartha Kitt, Boomerang!

Boomerang

(1992)

Embarrassing sex in ”Boomerang”

THE CHARACTERS Marcus Graham (Eddie Murphy, right), a womanizer and hotshot marketing executive, and Lady Eloise (Eartha Kitt, left), the aged figurehead of a cosmetics company

THE SCENE Believing he must sleep with Lady Eloise to advance his career, Marcus grits his teeth and allows the lingerie-clad sexagenarian to seduce him.

EMBARRASSMENT QUOTIENT Fairly high for Marcus, who learns later that sleeping with Lady Eloise could not have helped his career after all. Higher, perhaps, for Kitt, whose character’s senior-citizen sexual appetite is supposed to seem grotesque. (But come on, this is Eartha Kitt — the former Catwoman exudes sex appeal at any age.)

EW MOVIE GRADE C-

Bridget Jones's Diary

Bridget Jones’s Diary

(2001)

Embarrassing sex in ”Bridget Jones’s Diary”

THE COUPLE Bridget Jones (Renée Zellweger, right), slightly pudgy queen of the singletons, and Daniel Cleaver (Hugh Grant, left), her caddish but charming boss

THE SCENE Hoping for a night of passion with Daniel, Bridget must decide: Should she wear the ”granny” panties, the ugly undergarment that will flatten her tummy, or a pair that will allow a midriff bulge but will look sexier once she takes her skirt off? She picks the former, much to her chagrin when she does end up in bed with Daniel, who ridicules her choice.

EMBARRASSMENT QUOTIENT Fairly high for Bridget, though not as humiliating as having slept with the lothario in the first place, against her better judgment.

EW MOVIE GRADE B

Woody Allen, Howard Cosell, ...

Bananas

(1971)

Embarrassing sex in ”Bananas”

THE CHARACTERS Product tester-turned-Latin American revolutionary Fielding Mellish (Woody Allen, left) and political activist Nancy (Louise Lasser, center)

THE SCENE As Fielding and Nancy consummate their marriage under the covers, legendary ABC sportscaster Howard Cosell (right) is on hand to give the play-by-play, as well as to conduct the post-game interviews.

EMBARRASSMENT QUOTIENT High for Fielding, who has to defend a performance that was apparently not his A-game.

EW MOVIE GRADE A-

Rob Schneider, Deuce Bigalow: Male Gigolo

Deuce Bigalow: Male Gigolo

(1999)

Embarrassing sex in ”Deuce Bigalow: Male Gigolo”

THE CHARACTERS Deuce Bigalow (Rob Schneider, left), fish tank cleaner-turned-reluctant ”man-whore,” and Kate (Arija Bareikis, right), a sweet young woman whose friends have set her up on a blind date with Deuce

THE SCENE Deuce and Kate strip down and are engaging in foreplay when he discovers her secret: a prosthetic leg, which Deuce has accidentally detached.

EMBARRASSMENT QUOTIENT High for Deuce, higher still for Kate

EW MOVIE GRADE D

Luke Wilson, Old School

Old School

(2003)

Embarrassing sex in ”Old School”

THE COUPLE Mitch (Luke Wilson, left), an attorney, and Heidi (Juliette Lewis, right), his girlfriend

THE SCENE Mitch comes home early from a business trip and surprises Heidi, whom he finds in bed watching a porn video. Mitch is excited, until Heidi’s guests, a couple of naked, blindfolded swingers, pop out of the bathroom and nearly give him a heart attack. ”Please be honest with me. Tell me this is the first time this has ever happened,” Mitch says. ”Well,” Heidi replies, ”do you want me to be honest or do you want me to tell you this is the first time?”

EMBARRASSMENT QUOTIENT High — and later compounded by Mitch’s reference to the incident during a drunken toast at the wedding of his friend Frank (Will Ferrell).

EW MOVIE GRADE C+

M*A*S*H

M*A*S*H

(1970)

Embarrassing sex in ”M*A*S*H”

THE CHARACTERS Major Margaret Houlihan (Sally Kellerman), an Army nurse during the Korean War, and Major Frank Burns (Robert Duvall), an Army surgeon

THE SCENE The straitlaced officers give in to their mutual attraction in the privacy of Margaret’s tent (above left), but camp pranksters place a microphone under the bed, broadcasting the couple’s passion to the entire camp via loudspeaker (above right).

EMBARRASSMENT QUOTIENT Extreme. If you’ve only seen the sitcom version of M*A*S*H, you need to see this scene to learn how Margaret earned the nickname ”Hot Lips.”

EW MOVIE GRADE B+

The Crying Game

The Crying Game

(1992)

Embarrassing sex in ”The Crying Game”

THE CHARACTERS Fergus, a.k.a. Jimmy (Stephen Rea, right), an IRA member on the lam in London, and hairdresser Dil (Jaye Davidson, left), the bereft sweetheart of the English soldier Fergus was ordered to kill

THE SCENE The guilt-ridden Fergus finds himself drawn to the alluring Dil, and the pair get hot and heavy until Dil disrobes before the Irishman, revealing that she’s actually a he.

EMBARRASSMENT QUOTIENT Off the charts, both for Fergus, who becomes violently sick, and for Dil, who can’t believe that ”Jimmy” didn’t already know.

EW MOVIE GRADE A