100 Greatest Celebrity Scandals Of All Time

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100 Greatest Celebrity Scandals Of All Time

Celebrity scandals not only make for great reading, but say a lot about human nature. This is why we’re launching Scandalist with the 100 Greatest Celebrity Scandals Of All Time. We began this project by researching and gathering the follies of more than 250 celebrities. After whittling the list down to the 100 most essential, we locked ourselves in a conference room and nearly came to blows before agreeing on a final order. The scandals range from funny (Tom Cruise freakout) to sexy (Kim Kardashian‘s ass) to depraved (Charles Manson) to world-affecting (Monica‘s BJ’s).

In each post, we highlight where the scandal hit in the arc of each celebrity’s career and what impact it had on them. As a whole, these scandals provide a gold mine of odd trivia and pop culture memorabilia. Ever hear that Mick Jagger was rumored to have eaten a Mars Bar out of singer Marianne Faithfull‘s vagina? Or that Barry Bonds‘ Hall Of Fame ball literally has an asterisk on it? Read through all 100 juicy scandals, browse the list below, or skip ahead to the Top 10. Dig in!

#100: Winona Ryder Likes To Steal
#99: Pat O’Brien’s Dirty Voicemails
#98: Pee-Wee Herman’s Indecent Exposure
#97: Sinead O’Connor Rips Up Pope Picture
#96: Mick Jagger Eats Candy Out Of Marianne Faithful’s Vagina?
#95: Kim Kardashian Sex Tape
#94: Lil’ Kim Jailed For Perjury
#93: Liza Minnelli And David Gest Marry, Divorce
#92: Dave Chappelle Bails On Chappelle’s Show
#91: Todd Bridges’ Drug Woes
#90: Matt Damon Dumps Minnie Driver on Oprah
#89: Vanessa Anne Hudgens’ Nude Photos
#88: Angelina Jolie Makes Out With Her Brother
#87: Karrine “Superhead” Steffans Publishes Tell-All
#86: David Hasselhoff’s Drunken Hamburger Viral Video
#85: Mariah Carey’s TRL Meltdown
#84: Whitney Houston: Crack Is Whack
#83: Kobe Bryant Rape Trial
#82: Diddy Midtown Shooting Trial
#81: Madonna And Britney Kiss
#80: Bill O’Reilly Loves Vibrators, Phone Sex
#79: Rush Limbaugh Is A Drug Addict
#78: Nick Hogan Crashes His ‘Pussy Magnet’
#77: Amy Winehouse Is A Drug Addict
#76: Eddie Murphy’s Transvestite Prostitute
#75: Courtney Love’s Heroin Binge
#74: Kate Moss Cocaine Video
#73: Eminem’s Relationship With Kim
#72: Salman Rushdie’s Death Warrant
#71: John Belushi Overdoses
#70: Studio 54 Bust
#69: Tom Cruise Loses His Cool
#68: River Phoenix Overdoses
#67: Rick James Tortures People
#66: Richard Gere Rumored To Stick Gerbils Up His Butt
#65: Mike Tyson Convicted Of Rape
#64: Elvis Presley Dies At 44
#63: Hugh Grant Busted For Soliciting Prostitute
#62: Jane Fonda Endorses North Vietnamese
#61: Hell’s Angels Wreak Havoc At Altamont
#60: Paris Hilton Goes To Jail
#59: Jack Johnson Becomes First Black Heavyweight Champ, Riots Ensue
#58: Brad Dumps Jennifer For Angelina
#57: Heidi Fleiss’s Prostitution Ring Busted
#56: Alec Baldwin’s Abusive Voicemail Rant
#55: Deep Throat Prompts Obscenity Trial
#54: Martha Stewart Busted For Insider Trading
#53: Sex Addict Bob Crane Murdered
#52: Don Imus Spews Racist Remarks
#51: Lorena Bobbit Severs John Bobbit’s Penis
#50: Oliver Stone’s JFK Sparks Controversy
#49: Michael Vick: Dog Killer
#48: Fatty Arbuckle Charged With Rape, Murder
#47: Marilyn Manson Blamed For Columbine Shootings
#46: James Frey Writes A Million Little Lies
#45: Washington D.C. Mayor Marion Barry Crack Bust
#44: Mel Gibson’s Anti-Semitic Rant
#43: Robe Lowe Sex Tape
#42: Robert Downey, Jr. Has Drug Problems
#41: Milli Vanilli Lip-Synch
#40: Phil Spector Charged With Murder
#39: The 27 Club
#38: Michael Richards Loses It On Stage
#37: Lou Pearlman Indicted
#36: Chuck Berry’s ‘Toilet Tapes’
#35: Lisa ‘Left-Eye’ Lopes Burns Down Andre’s House
#34: Tonya Harding Has Nancy Kerrigan Clubbed
#33: Heath Ledger Overdoses
#32: Jimmy Swaggart Caught With Prostitute
#31: Barry Bonds’ Steroid Scandal
#30: Gram Parsons’ Corpse Stolen
#29: Ted Kennedy Goes For A Dip At Chappaquiddick
#28: Paris Hilton Sex Tape
#27: Paula Abdul Boinks American Idol Contestant
#26: New York Governor Eliot Spitzer Likes Prostitutes
#25: Jerry Lee Lewis Marries His 13-Year-Old Cousin
#24: Lindsay Lohan Melts Down
#23: R. Kelly Child Porn Trial
#22: Vanessa Williams Dethroned
#21: Amy Fisher Shoots Joey Buttafuoco’s Wife
#20: Anna Nicole Smith’s Death
#19: Sid Killed Nancy. Or Did He?
#18: Patty Hearst Is Kidnapped
#17: Kurt Cobain Commits Suicide
#16: Marvin Gaye Murdered By His Father
#15: JonBenet Ramsey Sexually Assaulted, Murdered
#14: Marilyn Monroe Dies Under Mysterious Circumstances
#13: Kanye West: ‘George Bush Doesn’t Care About Black People’
#12: The Roman Polanski Rape Trial
#11: John Lennon Murdered
#’s 10-1: The Top 10 Scandals

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#100: Winona Ryder Likes To Steal

After stealing a handful of rock stars from their long-term paramours (Remember Soul Asylum‘s Dave Pirner? Neither do we), Winona Ryder revealed that she also had a penchant for stealing high-end couture, after getting busted for shoplifting at a Beverly Hills Saks in December 2001. Surveillance cameras caught the then-30-year-old star acting about half her age, as she tried to slip out of the store with more than $6,000 worth of merchandise.

The cherry on top of this mess: painkillers were found in Winona’s purse. A prescription for them was not. Suddenly, her brief but very public association with Courtney Love around that time made a lot more sense. Winona subsequently treated her arrest as, like, no big deal. She poked fun at the whole episode during a bizarre stint as the host of Saturday Night Live (“I love free stuff!”), and appeared on the cover of W magazine wearing one of those “Free Winona” t-shirts. Kids, they never learn.

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#99: Pat O’Brien’s Dirty Voicemails

Poor Pat O’Brien. Car accidents, overdoses, violent standoffs with police — these are more-than-acceptable reasons for a lifelong drug addict to finally seek professional help. But the release of pornographic voice mail messages? That’s awfully hard to glamorize.

The host of TV’s The Insider and long-time sports commentator was once associated with awkward attempts at being hip (remember Diddy‘s “Bad Boy For Life” video?), but thanks to some unfortunate drunk dialing in 2005, Pat will go down in history as the guy who wanted to “go f*cking crazy,” inviting his anonymous crush to join him and “Betsy” for a sex romp. So graphic were the messages that “Get another woman up, hire a hooker. Let’s get crazy, get some coke” is the kid-friendly part.

Pat followed his rehab stint with a Dr. Phil primetime special, but the self-help guru’s advice wasn’t enough to keep him from heading back less than three years later. Though the mockery of his sexploits continues (“I am so f*cking into you. You have to pay attention to Betsy, but let’s have fun!”), Pat’s career hasn’t taken too much of a hit. He’s still hosting The Insider and recently announced plans to marry his girlfriend of five years … Betsy. The couple that goes f*cking crazy together stays together!

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#98: Pee-Wee Herman’s Indecent Exposure

The most surprising thing about Paul Reubens‘s 1991 arrest wasn’t what he got busted for — namely, exposing himself in a Florida adult movie theatre — but what he was watching at the time: an XXX film called Nurse Nancy. Huh? Wasn’t Reubens gay? What was next? News that Pee Wee Playhouse‘s Chairy was a tranny?

Legally, the incident was no biggie: Reubens pleaded no contest and was fined $135. Professionally, it was a different story. Reubens’s arrest sparked public outrage, since he was known primarily as the host of the kid-friendly Pee-Wee’s Playhouse. And the incident seemingly marked the death-knell for his once-beloved character. The show was immediately yanked from the air, and Pee-Wee Herman dolls were tossed from toy-store shelves.

But a Pee-Wee comeback might be on the horizon. A big-screen version of Playhouse has reportedly been greenlighted by Paramount, with a projected 2009 release. Ruebens’s next stint at a movie theater is bound to go better than his last.

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#97: Sinead O’Connor Rips Up Pope Picture

The most important thing Sinead O’Connor destroyed on the October 3, 1992 episode of Saturday Night Live wasn’t a picture of Pope John Paul II, but her career. If you watched O’Connor’s performance the one and only time it officially aired (Comedy Central reruns substitute the dress-rehearsal performance, which features O’Connor holding up a picture of a little girl without ripping it), you knew something weird was up. She sang a positively frightening A cappella rendition of Bob Marley‘s “War,” substituting in a lyric about child abuse. When she got to a line about evil, she held up a picture of the then-Pope, snarled, “Fight the real enemy!” and tore it up. The shocked silence from the audience gave no indication of the furor that would follow: she was publicly threatened with violence, loudly booed at a Bob Dylan tribute concert at a few weeks later, and record sales and radio play shriveled into nothing.

Though not explicitly stated, her move on Saturday Night Live was meant as a swipe at child abuse in the Catholic Church. In 2002, when the Church was rocked by a scandal that involved child-molesting priests, Salon.com asked O’Connor if she would have done anything different that night on SNL. Her response: “Hell no!”

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#96: The Myth That Mick Jagger Ate Candy Out Of Marianne Faithful’s Vagina

Nowadays the Rolling Stones look like something out of The Nightmare Before Christmas. In 1967, though, the “Gimme Shelter” rockers were Public Enemy No. One, thanks to their affinity for sex and drugs. It was only a matter of time before the cops came knocking. Following a tip-off from the tabloid press, 20 police officers raided Keith Richards‘ Redlands estate in England. Richards and Mick Jagger were charged with possession of LSD and other narcotics, but the raid became legendary for a candy bar involving singer Marianne Faithful.

Cops on the scene swore they interrupted Jagger eating a Mars Bar wedged into his girlfriend’s holiest of holies before hauling him away for possession. “A cop’s idea of what people do on acid!” sniffed Faithfull, denying all in her autobiography. Even so, the story remains one of rock’s most celebrated myths. — Charles Bottomley

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#94: Lil’ Kim Jailed For Perjury

Lots of rappers say they won’t snitch, but Lil’ Kim has the perjury conviction to prove it. When her entourage got into a shootout with friends of rival Foxy Brown in downtown Manhattan following a Hot 97 interview in February 2001 (leaving one injured), the trash-talking sex freak behind hits like “How Many Licks?” and “Magic Stick,” told police she hadn’t been near the shooting. She changed her tune in front of a grand jury, but asserted that manager D-Roc, a shooting suspect, wasn’t present, and that she didn’t even know bodyguard C-Gutta, also accused. After witnesses had them leaving the scene in the same limo, D-Roc and C-Gutta were sentenced to over ten years each, and Kim was up for perjury.

Lil’ Kim claimed innocence – how was she expected to remember if her manager had shot people in front of her? But thanks to damning testimony from Junior M.A.F.I.A. members Cease and Banger, she was found guilty and sentenced to a year and a day for being less than forthcoming. [Photo: Getty]

by (@katespencer)

#92: Dave Chappelle Bails On Chappelle’s Show

If the entertainment biz was high school back in 2005, Dave Chappelle was the Big Man On Campus. The comedian rose quickly in the New York stand-up circuit, and broke into film at the age of twenty, starring in Mel BrooksRobin Hood: Men in Tights. After a few failed TV shows, a film flop (Half Baked), and the disastrous decision to turn down the role of Bubba in Forrest Gump, he scored a serious hit on Comedy Central with Chappelle’s Show.

Dave combined comedy sketches (which often commented on pop culture, race, and class issues) with stand-up and live hip-hop acts, and the formula worked. In just two seasons the show had legions of fans, earned two Emmy nods, and the Season One discs became the bestselling TV-series DVD of all time–surpassing the 3 million mark. TV execs freaked and forked over a $55 million contract to try and snag the star for two more seasons. Instead, in May 2005, Chappelle ran out during production of season three, hopping a plane to Africa and ending the show for good.

Dave later returned to the States, though not to the small screen. In his first interview since his bizarre meltdown, he told Oprah Winfrey, “I wasn’t crazy but it is incredibly stressful … I felt in a lot of instances I was deliberately being put through stress because when you’re a guy who generates money, people have a vested interest in controlling you.”

by (@katespencer)

#91: Todd Bridges’ Drug Woes

Todd Bridges paved the way for future f*cked-up child stars, carving out a destructive trail of drugs, violence, and murder that standardized the destiny of kid actors — especially those on his own hit show. The adorable teen — who ended his run as Willis Drummond on Diff’rent Strokes in 1986 — was busted just two years after the show’s end for attempting to murder a drug dealer while crazy on a coke binge. The actor was acquitted, but found himself facing the same charge in 1997 after attacking someone with a car — and was acquitted once more, making him one of the only child stars ever to experience good luck in later life.

Co-stars Dana Plato and Gary Coleman also endured the rough reality of post-sitcom fame. Dana posed for Playboy, was busted for drug possession a few times, and OD’d in 1999 at age 35. Gary went bankrupt and was nailed for assault while working as a security guard. But it was Todd — the first of the three to fall — who would prove the only one to come out OK on the other side of disaster.

The actor finally got sober and now spends his time speaking to kids about the dangers of drugs (he’s an expert, clearly), and attempting a second go at fame on shows like Skating with Celebrities and Everybody Hates Chris. Of his murky past, Todd admits, “The bottom line is I’ve made stupid choices. But I got my life together now and that’s the difference. I’m not the same idiot I used to be.”


by (@katespencer)

#90: Matt Damon Dumps Minnie Driver on Oprah

Matt Damon and Minnie Driver fell in love while the rest of the world was going gaga over their surprise 1997 hit, Good Will Hunting. But while Matt’s character chases after Minnie at the end of that mushy flick, their actual affair ended awkwardly and abruptly when he denied having a girlfriend during an appearance on The Oprah Winfrey Show.

After her man confessed in front of millions that their relationship was amicably over (and had been for a couple of weeks), Minnie milked her newfound rep as the woman scorned, referencing Damon’s dumping in interviews and telling The Los Angeles Times, “It’s unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.”

Even less appropriate was Matt jumping in bed with Winona “Sticky Fingers” Ryder just weeks later. Will Hunting may have been good, but the guy who played him was a straight-up bad boy.