100 Greatest Celebrity Scandals Of All Time

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#89: Vanessa Anne Hudgens’ Nude Photos

Vanessa Hudgens became a hit with the tween set by starring in Disney’s wildly popular made-for-TV movie series High School Musical, but it wasn’t until her nudie pics hit the Internet that she became a household name. In the most notorious photo, a full-frontal naked shot, taken when Vanessa was only 15 years old, she’s standing erect with her legs spread open suggestively and a sassy, coming-of-age smile on her face.

Landing on computer screens worldwide on September 6, ’07 (just a few days before HSM 2 premiered on TV), the photos made national headlines and dashed Vanessa’s G-rated image almost overnight. To combat the media scrutiny, she apologized to the public: “I am embarrassed over this situation and regret having ever taken these photos.” Turns out, Vanessa photographed herself in her bedroom and supposedly sent the pornographic results to torture a boy toy that she’d dumped. “It was like she was saying: ‘Look what you’re going to miss,’” her then-boyfriend Adam O’Neal told The National Enquirer.

Disney stuck by its star, and Vanessa’s career is now on fire. Not only does she endorse Marc Ecko‘s clothing line, but she has a second pop album in the works and is landing Hollywood roles. In fact, she’s set to play a 15-year-old girl who gets tangled up in a romance in Will. When the movie’s released next year, she’ll be 21. So this time you can look.

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#88: Angelina Jolie Makes Out With Her Brother

Angelina Jolie‘s career was on fire when she shockingly open-mouth-kissed her older brother James Haven at the 2000 Oscars ceremony. She accepted the Academy Award for Girl, Interrupted and then, from the stage of the Shrine Auditorium in Los Angeles, proceeded to gush about how much she was “in love with” James.

Rumors circulated that the siblings were having an incestuous affair, and many didn’t put the possibility past the 24-year-old actress, who had proudly admitted to a proclivity for sexual experimentation — from a lesbian affair with her female co-star Jenny Shimizu to S&M fun with her first husband, Jonny Lee Miller. “You’re young, you’re drunk, you’re in bed, you have knives — shit happens,” she said of her relationship with Miller.

Still, the siblings insisted that their little game of tonsil hockey was blown way out of proportion. As Angelina explained, “Friendship between siblings of divorced parents is very close.” [Photo: Getty]

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#87: Karrine “Superhead” Steffans Publishes Tell-All

Karrine “Superhead” Steffans doesn’t just shake her booty in your favorite rap videos. She’s also slept with most of your favorite rap stars. The list includes Lil’ Wayne, Method Man and even a few ringers like Shaquille O’Neal and Bill Maher. And her acrobatic tongue eventually earned her the nickname “Superhead.”

Steffans blew the lid off her love life in the memoir Confessions of a Video Vixen, which landed on bestseller lists in 2005. The pneumatic 25-year-old told of breathless encounters with DMX, Diddy, Jay-Z, Xzibit, Dr. Dre, Ice T, Usher, Bobby Brown and Vin Diesel during her years in Hollywood. Breathless, that is, until the morning after, when Steffans would discover that she was left with more crabs than self-respect.

In the sequel, The Vixen Diaries, Steffans was at it again, alleging that ex Darius Morgan cheated on her with Tyson Beckford. In his own tell-all published in 2008, Bobby Brown downplayed Steffans’ contributions to literature. “I’ve spent several nights at her house,” he wrote. “But she was only good for what her nickname stood for.” — Charles Bottomley

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#86: David Hasselhoff’s Drunken Hamburger Viral Video

Fame’s a bitch. One minute you’re riding high in red trunks, sharing screen time with Pamela Anderson on the nation’s biggest television show. The next, you’re drunk and shirtless and eating a cheeseburger on the floor of your Vegas hotel room, being videotaped by your 16-year-old daughter.

In May 2007, while starring in a Vegas production of The Producers, David Hasselhoff had little else to boast about besides a rabid fan-base in Germany. Since his starring roles on Knight Rider and later Baywatch, the Hoff’s career had taken some hits, and in addition to mostly playing himself in cameos, he’d also developed a drinking problem. And then he found himself in the midst of an acrimonious divorce from his wife of 15 years.

This viral video, which his daughter shot with intent to show Dad the error of his ways, features him slurring his words and gnawing on a burger (when he can get it up to his mouth, that is). As his daughter pleads with him to stop drinking, the Hoff can only murmur, “I have trouble in my life,” and chew with eyes half-lidded. “This is a mess,” Hoff sputters as he drunkenly drips Secret Sauce all down his bear-rug of a chest. You said it!

by (@katespencer)

#85: Mariah Carey’s TRL Meltdown

By 2001, Mariah Carey‘s star was so big it was destined to burst, but who knew the diva would spur her own implosion?! Maybe the endless #1 hits drove her mad, or her divorce from Tommy Mottola. Maybe her heels were just too high that day. Regardless, Mimi showed up on MTV’s TRL in July 2001 pushing an ice-cream cart — and managed to be the only thing to melt down.

Sporting little more than a T-shirt, Mariah handed out popsicles to the baffled crowd as she began a bizarre striptease (supposedly to promote her soon-to-be flop film Glitter), yanking off her tee to reveal a skimpy tank and booty shorts. “I just want one day off when I can go swimming and eat ice cream and look at rainbows,” she slurred as she sexed up the teenaged crowd. She followed this strange display with rambling voicemails on her website revealing she was “a little too paranoid about life. … What I’d like to do is just a take a little break or at least get one night of sleep … guess what, I don’t take care of myself.” Later that month she got her wish when she was hospitalized for “exhaustion.” After switching labels and taking some time off, Mariah reclaimed her status with the hit albums The Emancipation of Mimi and E=MC2 and her marriage to the much-younger hottie Nick Cannon — proving in the end that a little bit of craziness never hurts.

In 2007, she opened up about her ordeal, telling Interview, “I consider the breakdown a breakthrough. I needed to hit rock bottom. … But was I out of control at that moment? Yes.”

[Photos: Getty/WireImage]

by (@katespencer)

#84: Whitney Houston: Crack is Whack

We all knew Whitney Houston wanted to dance with somebody, we just had no idea she’d end up waltzing with a crack pipe. The singer had barreled through the ’80s and ’90s racking up #1 hits and the occasional flop (like marrying the dysfunctional Bobby Brown). After selling over nine million copies of The Bodyguard soundtrack and stockpiling six Grammys, she decided to move on to something more, uh, super f*cking illegal.

In early 2000, Whitney was busted lugging weed through a Hawaii airport. As if that wasn’t bad-ass enough, she inspired Lohans everywhere by skipping shows and losing enough weight to scare even Nicole Richie. Chatting with Diane Sawyer in 2002, she admitted to, well, everything. “My business is sex, drugs, rock and roll … I partied a lot.” When asked by Sawyer about her drug of choice — “Is it alcohol? Is it marijuana? Is it cocaine? Is it pills?” — Whitney answered, “It has been at times.” Sawyer: “All?” Houston: “At times.” But even Whitney had her limits: “I make too much money for me to ever smoke crack … crack is whack.” Whack enough to send the fallen songbird to rehab in 2004. She has yet to make a solid comeback — unless having her husband yank a “doody bubble” from her ass counts — but at least she’s made headlines dumping Brown for Ray J., brother of Brandy and on-camera lover of Kim Kardashian.

Whitney’s daughter is possibly continuing the family addiction tradition. Pics of then 13-year-old Bobbi Kristina exhaling what looked like marijuana smoke popped up on the Web in 2007. So much for teaching children well and letting them lead the way.

by (@katespencer)

#83: Kobe Bryant Rape Trial

As the first NBA player drafted right out of high school, Kobe Bryant was living the epitome of a perfect life — Prom with Brandy! Hot teenage wife! $40 million a year in pay and endorsements! — when he suddenly and stupidly f*cked up all his fame and fortune in an instant. On July 18, 2003, while in Colorado for surgery, Kobe banged a 19-year-old former cheerleader working at his hotel. Shortly after the incident she came forward and charged the Lakers star with sexual assault, throwing a wrench into his perfect world.

Bryant admitted to the adultery, and — in the most pathetic and pricey attempt at an apology ever — bought his wife a $4 million 8-carat diamond ring so she could wear his shame on her finger. Everything from the victim’s semen-stained panties to Kobe’s kinky fetishes (such as grabbing the victim’s neck while penetrating her from behind, then asking permission to ejaculate on her face) was fair game in the trial. But the baller denied the charges of assault, and the case was dropped when the victim refused to testify. She later brought a civil suit against Kobe, which was “resolved to the satisfaction of both parties.” In other words, she got some cash ya’ll!

As the scandal dust settled, Kobe’s star rose again thanks to his MVP status and his feud with former Lakers teammate Shaquille O’Neal — and, of course, that massive diamond ring.

by (@katespencer)

#82: Diddy Midtown Shooting Trial

By the late nineties, Diddy, then know as Puff Daddy, had already endured his share of scandals, mixed with massive success. After thriving as an intern-turned-executive at Uptown Records, he jumped shipped to start his own label, Bad Boy, which launched countless hip-hop stars. Diddy also found fame as a rapper, and was soon wildly partying in Hollywood, the Hamptons, and St. Tropez. Bad Boy’s growing rivalry with West Coast label Death Row exploded with the 1997 shooting of Biggie Smalls. It seemed as if Biggie’s tragic death (and that of Tupac Shakur) would inspire Diddy to finally drop the drama and settle down.

Instead, he hopped in bed with bombshell Jennifer Lopez, who was quickly rising to the top of the tabloids as a talented triple-threat. On December 27, 1999, the pair was out at Club New York in Manhattan with Diddy’s crew, when gunfire broke out. The mogul, along with his then-protégé Shyne, was arrested after his driver turned him in, accusing his boss of attempting to bribe him into taking the weapon used in the shooting. The seven-week trial in 2001 hogged headlines across the country. Diddy, obviously exhausted, was shaking as the jury handed down their decision: acquittal. (Shyne‘s fate wasn’t nearly as blessed; he was found guilty of weapons charges and assault, and landed in jail.)

Diddy later declared that the two-year ordeal had “made me deeper.” It also turned him back into a single man — he and J. Lo parted ways a few weeks later.

by (@katespencer)

#81: Madonna And Britney Kiss

Let us journey back in time, to a world where Britney Spears was beautiful and her golden locks were real (maybe). The year was 2003, the girls were decked out in white wedding dresses better suited for streetwalkers, and they only had eyes–or lips–for one lady: the Queen of Pop and Pointy Bras, Madonna. That September, Britney Spears and Christina Aguilera joined their idol onstage at the MTV Video Music Awards and turned a regular performance into headline news when they each took turns tongue-kissing Madge while singing her timeless tramp anthem “Like a Virgin.”

The timing of their tonsil hockey was perfect, providing a much-needed jolt to Brit’s suffering career. It had been a tumultuous year of disappointing record sales, a high-profile breakup from Justin Timberlake (which inspired his #1 hit “Cry Me a River”), her disastrous film flop Crossroads, and the closing of her restaurant NYLA after just seven months. Plus she had a new album to promote, packed with horny dance tracks celebrating masturbation and other hot ‘n’ breathy behavior. Yup, a girl kiss is just what she needed. Britney later claimed she had “never kissed a woman before” — even though they had seriously rehearsed the smooch before the actual performance. (Sadly, an ass-slap from Madge was canned before they went live.) Still, that one sultry, same-sex lip-lock freaked the pundits and titillated our whole nation. And our girl finally became a (bi-curious) woman.


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#80: Bill O’Reilly Loves Vibrators, Phone Sex

In October of 2004, conservative Fox News host Bill O’Reilly was sued for sexual harassment by Fox News producer Andrea Mackris. According to Mackris and her attorneys, O’Reilly’s abusive conduct included talk of vibrators, phone sex, a ménage a trois, the size of “not-so-little-Bill,” vivid sexual fantasies involving hot falafel-on-vagina action, and how the guy that runs Fox News was going to have Al Franken assassinated.

According to the lawsuit, on at least one occasion, O’Reilly used the vibrator on himself while on the phone with Mackris. It doesn’t say how exactly he used the vibrator on himself, but putting it in his butt and/or fellating it are not explicitly ruled out in the filing.

Much of the abuse detailed in the lawsuit allegedly happened after Mackris returned to Fox News after a brief stint at CNN. Mackris and her attorney never admitted to having taped any of these conversations, but based on the detail contained in the lawsuit, Fox most likely believed O’Reilly had been caught in the act. It’s doubtful that the following passage where O’Reilly gets a loufa confused with a falafel could have been made up:

“So anyway I’d be rubbing your big boobs and getting your nipples really hard, kinda’ kissing your neck from behind … and then I would take the other hand with the falafel thing and I’d put it on your p*ssy but you’d have to do it really light, just kind of a tease business…”

O’Reilly eventually settled out of court, agreeing to drop his own extortion suit (which was actually filed first) against Mackris and her attorneys. O’Reilly never admitted guilt and never apologized.