The Most Shocking Celebrity Sex Scandals

Office Romance

The Celeb: David Letterman

The Scandal: You know that old cliché about not dipping your pen in the office ink? Well, it's safe to say that David Letterman's pen hasn't run dry during his years hosting the 'Late Show.' On Oct. 1, the TV host openly admitted to sleeping with members of his female staff after someone - allegedly 'CBS News' producer Robert J. "Joe" Halderman -- threatened to out Letterman's sexual exploits via a biographical screenplay. Instead of forking over the $2 million that the blackmailer requested, Letterman chose to air his dirty laundry all on his lonesome, making his office a no-go zone for scores of wide-eyed interns, according to the New York Post. Letterman played off the scandal by including jokes about it into his monologue, and since the initial admission, the uproar seems to have died down ... for now.

What would have made it even more shocking: If Letterman had managed to stimulate the media economy whilst stimulating his staff.

Taboo

The Celeb: Mackenzie Phillips

The Scandal: After decades of silence, the former 'One Day at A Time' sitcom star did what everyone does when they want to air their grievances/seek salvation: She went on the 'Oprah Show .' On air, she revealed to the great dame of daytime that she had been raped by her father -- John Phillips of he Mamas & the Papas -- in a drug-induced stupor at the age of 17 or 18. The teen star then engaged in a 10-year consensual sexual relationship with her dad. The reason for this shocking confession? The impending release of her tell-all autobiography, 'High on Arrival.'

What would have made it more shocking: If Phillips had resisted writing a tell-all, and merely told-all to her therapist.

Prostitution

The Celeb: Hugh Grant

The Scandal: Hugh Grant was the basset hound-eyed British fop that made all the girls swoon, the darling dandy, the perfect gentleman -- that is, until he was arrested on the Sunset Strip while receiving oral sex from a prostitute in 1995. It was the trick heard round the world: Why did the dapper star, who was dating super hot model Elizabeth Hurley at the time, pay for sex when he was, essentially, a sex symbol? Although the only answer that Grant had for the public -- and Jay Leno -- amounted to, "I did a bad thing," the Anglo actor did have the grace to apologize. And apologize. And apologize. On any talk show that would have him.

What would have made it more shocking: If Grant's relationship with Hurley had survived instead of his career.

Indecent Exposure

The Celeb: Paul Reubens

The Scandal: We were already slightly creeped out by Chairry, the talking easy chair on Paul Reubens' 'Pee-Wee's Playhouse,' but the energetic TV star took the wig factor to a new level when he was arrested at a porn theater for indecent exposure in 1991. Although Reubens denies whipping out little Pee-Wee in public to this day, he's racked up the bizarro points over the years: According to 'Dateline' he was arrested for possession of child pornography a decade later, and he recently appeared on the 'The Jay Leno Show' in full Pee-Wee garb, flashing what he calls an abstinence ring. Forget Sir Arthur C. Clarke, Reubens is the real author of childhood's end.

What would have it more shocking: If Reubens had been caught cavorting with his chair rather than pleasuring himself while sitting in it.

Adultery

The Celeb: Barbara Walters

The Scandal: Another addition to the "Oh, I never even pictured that person having sex" canon, Barbara Walters shocked geriatrics and housewives across the nation last year when she admitted in her tell-all book, 'Auditions,' that she had had an affair with married U.S. Senator Edward Brooke back in the '70s. Both were pioneers in their fields -- Walters broke down barriers as strong female news anchor and Brooke was the first African American to be elected to the Senate. Consequently, neither wanted to jeopardize their budding careers by making their tryst public. You know, until one of them could get a book deal out of it.

What would have made it more shocking: If this affair had come to light, oh, 30 years ago.

Sex Tape

The Celeb: Dustin Diamond

The Scandal: Countless stars have had sex tapes, but back in 2006, Dustin Diamond achieved super-skeeviness when his sex tape, titled 'Saved By The Smell,' was leaked onto the Internet. The gossip pages were buzzing that Diamond was behind the release of the tawdry tape, but the 'Saved by the Bell' star denies that claim. He told PopEater in a recent interview about his tell-all book (because what other kind of book is there?), "No [I was not behind the leak]. Who wants to watch me? The problem is with guys that do videos is no regular guy can be an adult film star because we'd all be looking at the camera. No one wants to see me reaching over to the nightstand eating peanuts and M&Ms halfway through. No one wants to see that. I'm not Angelina Jolie."

What would have made it more shocking: If the film had featured Angelina Jolie.

Messed-Up Marriage

The Celeb: Woody Allen

The Scandal: If Mia Farrow thought she was having parenting troubles in 'Rosemary's Baby,' she had another think coming.
Farrow's ex-lover, Woody Allen, had quite the rep for playing the nebbish Casanova in his numerous films, but in 1997 he lived up to his creepy potential when he married Soon-Yi Previn, Farrow's adopted Korean daughter. Allen was 62, Previn, 27. The actress brought the girl to the U.S. when she was just eight, after which Farrow and Allen dated for a decade. During those years, the May/December love affair began. According to CNN, it wasn't until Farrow found naked photos of 21-year-old Previn in Allen's apartment that she learned the truth about her daughter and boyfriend's relationship. And now, more than a decade later, the pair is still together, making our skin crawl after all these years.

What would have made it more shocking: If Previn were also revealed to be the spawn on the devil.

Bathroom Sex

The Celeb: George Michael

The Scandal: Nearly a decade before Senator Larry Craig got his toes tappin' in an airport bathroom, the sexy, stubbled pop star came out of the closet by coming out of the stall--after he was arrested at Will Rogers Park in Beverly Hills for engaging in lewd conduct, according to 'Rolling Stone.' While teen girls collapsed in tears when they realized that their dreams of wedded bliss were no longer feasible, the rest of America let out a collective, "Duh" (it was 1998, after all).

What would have made it more shocking: If Craig had been in the stall with Michael.

Walking Scandal

The Celeb: Lindsay Lohan

The Scandal: Remember the good old days? When Lohan was busy remaking awesome kids movies like 'The Parent Trap' and 'Freaky Friday'? And 'Mean Girls'--wasn't 'Mean Girls' fun? Well, Lohan sure has grown up since those early film forays--grown up into a full-fledged train wreck. There's the rumored plastic surgery, the wardrobe malfunctions, the unfortunate nickname, the bogus sex tape, her girl troubles and her boy troubles. With all that scandal swirling around, it's a wonder she finds time to do things like act in films and sing. Oh, wait...

What would have made it more shocking: If it were revealed that Lindsay and her mother switched bodies sometime around when 'Mean Girls' hit cinemas. That would explain a lot.