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Pee-wee's Play(ing With Himself) House
This is not the Pee-wee Herman show the kids signed up for. It was anything but a stroke of genius when quirky TV comedian Paul Reubens was busted for indecent exposure and public masturbation in a Sarasota, Fla., porno palace in 1991. In fact, it was nearly professional suicide, but Reubens survived somehow, and slowly rebuilt some semblance of a career.
Madonna: Sex for Sale, $49.95
Everyone knows that sex sells, and nobody knows this better than Madonna, whose 1992 soft-core coffee-table book was predictably shocking enough to make massively good promo for her Erotica CD. Writing under the nom-de-sexy Mistress Dita, the book featured provocative photos of Madge and sparsely clad showbiz "gets" like Isabella Rossellini, Naomi Campbell and Vanilla Ice. Proving once again that Madonna knows how to work it—and it works!
Heidi Fleiss: Hollywood Fears her Little Black Book
Pimping ain't easy, but it beats working. The hugely successful Hollywood madam was ultimately laid low by a 1993 sting operation, but she didn't rat out her clients. Still, during her trial, info leaked out about her many celebrity johns, including Charlie Sheen. When asked about the matter, Sheen reportedly said, "I love sex and I can afford it." Once a charmer, always a charmer.
Hugh Grant: Divine Moment
File under: How to handle a sex scandal 101. After getting busted in June 1995 for lewd conduct in public for his streetside encounter with prostitute Divine Brown, Grant copped to it with candor and charm on the Tonight Show. "I think you know in life what's a good thing to do and what's a bad thing," he said, "and I did a bad thing. And there you have it."
Eddie Murphy: Dept. of Tranny-sportation
Murphy claims he was just being a Good Samaritan when he picked up a troubled transsexual hooker at 4:45 a.m. in West Hollywood back in 1997. Perhaps so, but he definitely wasn't being a Smart Samaritan as cops pulled him over and arrested his passenger. Maybe because he was filming Doctor Dolittle at the time, Murphy thought he could talk to the animals. Chatting up critters? OK. Tranny hookers? Not!
Pamela Anderson & Tommy Lee: The Tale of the Tape
Breaking new ground in amateur celebrity porn, the Baywatch babe and her not-so-little drummer boy's homemade 1998 honeymoon video was stolen and became one of the first burning Internet sensations. Pam and Tommy sued and were awarded $1.5 million in damages and a cut of the profits. Nice work if you can get it.
George Michael: Restroom with a View
Caught being a looky-loo in a Beverly Hills bathroom sting operation in 1998, Michael copped to a plea of engaging in a lewd act. He was fined and sentenced to community service, but he found a way to make the most of it with his music video for "Outside," featuring cops smooching in a disco-inferno urinal nightclub.
Paris Hilton: One Night in Paris
Shot in 2001 with then BF Rick Salomon, the Paris sex tape burst onto the scene like, well, we'd rather not say. Rick stayed classy (not) and got rich by releasing their formerly private moments for public viewing in 2004. After a lot of lawsuit ping-pong, Paris was awarded $400,000 but says she never got a penny. Regardless, Paris surfed this sordid wave onto the sunny beach of bigger fame.
Tiger Woods: Marriage in the Rough
Marketed as an upright family man, the world's top golfer turned out to be a player in the worst sense of the word as escorts, lady friends, alleged mistresses and dirty-text partners came out of the woodwork. In the end, maybe the moral of the story is that for some, even when you have it all, all you want is more.
Sandra Bullock, Jesse James & Bombshell McGee: Tats Entertainment
On the surface, girl-next-door Sandra and chopper dude Jesse seemed an odd couple. Deep down, too, as it turns out. The Monster Garage guy had demons, which he chose to exorcise by doing a bit of the inky-kinky with Nazi-costume-wearing model citizen Michelle "Bombshell" McGee—and reportedly several others! Maybe a leopard can't change his spots, or his tats, as the case may be.
Want more? Check out the 20 Years of Fashion Highs & Lows gallery!