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Charlie Toft

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Charlie Toft used to win awards for book criticism, but decided that reading was too much work. As a TV writer, his specialty is an encyclopedic and possibly unhealthy knowledge of American Idol.

Biggest Celebrity Sex Scandals

David Letterman had been better known for poking fun at sex scandals than starring in them, but last week’s bombshell that the late night host had been the object of attempted blackmail relating to his track record of sleeping with women on the staff of his show has earned him a spot on an unenviable list: pretty much the only place you’ll find Woody Allen, Paris Hilton, Eddie Murphy, and Pee Wee Herman hanging out together.

Yes, it’s the list of the greatest celebrity sex scandals of all time. Don’t blame us if this list could be outdated within hours of its publication. The scandals never stop. In alphabetical order:

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Woody Allen: It was one thing when the writer/director was just a lovable neurotic New Yorker, and quite another when he began an affair with the adopted daughter of his longtime girlfriend Mia Farrow. What made the incident especially troubling to many is that Allen has never understood why anyone would object to this relationship (which continues to this day), saying he was simply following his heart. Followed it over a cliff is more like it. Did this have a major impact on Allen’s career? Quick: Name three movies he’s made in this decade.

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Hugh Grant: In those pre-Heidi Fleiss days of 1995, the powerful men of Hollywood could have their illicit sexual needs fulfilled via a discreet call girl service, but someone forgot to tell Grant, busted for attempting to get his groove on with a Hollywood hooker. What made the scandal so newsworthy was the massive contrast between Grant’s onscreen image as the ultimate smooth British fantasy object and the caliber of his pickup, a streetwalker named Divine Brown. And of course, his arrest produced what still must be considered the greatest mugshot ever.

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Paris Hilton: As of autumn 2003, she was a moderately known socialite and bit player in films. But the release of a tape featuring a bored-looking Hilton going through the sexual motions, which was (coincidentally?) made public just before the premiere of her reality show The Simple Life, made her the massive Internet phenomenon she remains to this day. Quite a few celebs have learned that it is risky to mix sex and the camcorder, but Hilton and her friend Kim Kardashian have used their “scandals” as career moves.

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Vanessa Hudgens: The scandal here was pretty mild, as naughtiness goes: the leaking of a nude photo that was apparently taken in her own bedroom. It’s not like we haven’t all done that. But the uproar was spawned by Hudgens‘s age (she was still a teenager at the time) and the fact that the High School Musical franchise was pretty much all she was known for. Now that the actress has left high school behind and is competing with young Hollywood sex symbols for hot roles, this is a scandal she might not be too upset to have on her resume.

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Michael Jackson: Acknowledging up front that the King of Pop was never convicted of anything, it goes without saying that Jackson’s reputation was seriously damaged by the two allegations of sexual abuse of children made against him. Even the little Jackson did admit, most notably that he saw absolutely nothing wrong with sharing his bed with children, would be enough to land him on a list such as this. If he had just gone the normal rock star route and bedded of-age groupies, there would be no scandal. Sad but true.

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Rob Lowe: People expect a little bad boy attitude out of young men in Hollywood, but Lowe‘s career was significantly impacted by a sex tape (one of the first times that term had ever been used) made in 1988, when he was attending the Democratic National Convention. The contents of the tape would have been just embarrassing, but the revelation that one of the “women” in it was only sixteen put Lowe in potential hot water, even though his defense — that he assumed someone he met in a bar had to be of legal age — had some logic behind it.

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George Michael: One of the most prolific hitmakers of the 1980s has seemed to spend most of his last twenty years reasoning with the police over various drug and traffic violations. His brush with sex scandal came in 1998 with his arrest in a park bathroom on indecency charges during a sting run by the Beverly Hills police. Following the arrest, Michael made the official announcement that he was gay, which by that point was only news to those folks who had never seen the “Wake Me Up Before You Go-Go” video.

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Roman Polanski: The last several days have re-introduced a younger pop audience to one of the great Hollywood scandals of all time: Polanski’s plea of guilty on the charge of unlawful sexual intercourse with a thirteen-year-old girl in 1977. Despite Polanski‘s fame and undoubted genius as a director, this incident would likely be a footnote today were it not for his decision to flee the United States prior to sentencing. The details of the case have not gotten any less shocking with the passage of time.

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Paul Reubens: People could have guessed that the man behind Pee Wee Herman was probably sublimating some serious kinkiness, but few were prepared for his 1991 arrest on charges of indecent exposure in a Florida adult theater. While Reubens had been slowly putting Pee Wee on the backburner anyway, this incident brought a stunning end to his tenure on Saturday morning TV. Reubens has continued to work steadily as a character actor, but it has only been in recent weeks that he has announced plans to bring Pee Wee back.

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Vanessa Williams: The 1984 Miss America was forced to relinquish her crown after some nude photos she had taken during her modeling days were sold to Penthouse. In those more innocent times, the sight of a beauty queen posed in raunchy scenarios with another woman was truly shocking. It would be hard to argue that the scandal severely impacted her career, however, as the recording artist and Ugly Betty star is one of the very few ex-Miss Americas still in the public eye in a major way.


Categories: TV

Tags: David letterman, Hugh grant, Paris hilton, Vanessa hudgens, Woody allen