#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, asked O’Connor if she would have done anything different that night on SNL. Her response: “Hell no!”


#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]


#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

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)

#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.


#77: Amy Winehouse Is A Drug Addict

When Amy Winehouse‘s breakthrough album, Back to Black, hit U.S. shores in early 2007, it was hard to say which Winehouse was a bigger mess: the lovelorn persona on record who explicitly said no to rehab, or the drunken persona in public whose YouTubeable antics implicitly said no to rehab. Mere months later, that the latter had the much bigger problem was abundantly clear. Like oh-my-god-she-really-might-die-any-second-right-in-front-of-our-eyes clear.

Though capable of temporary composure (like her gorgeous performance of “Love Is a Losing Game” at the Mercury Prize Awards), Winehouse has spent the past year or so in a drug-induced haze. Publicity shots of her looking positively zonked appear virtually daily on blogs, and a YouTube clip surfaced in which she pulls something from her hair and seems to snort it.

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#75: Courtney Love’s Heroin Binge

Courtney Love sat down with Vanity Fair writer Lynn Hirschberg to debut herself as Nirvana front-man Kurt Cobain‘s wife with a rock star career of her own, but she ended up temporarily losing her newborn infant. “We went on a binge,” she told Hirschberg. “I did heroin for a couple of months.” The catch: her “binge,” in January1992, overlapped with her pregnancy.

When the article hit newsstands in September 1992, Children’s Services of L.A. removed baby Frances Bean from the Cobain household. After several months of legal wrangling (and a voicemail from Cobain calling Hirschberg and another reporter “insane c*nts”), the couple regained custody.

Despite her father shooting himself in the head when she was a toddler, being taken away yet again from her mother for 15 months when she was 12 (after Courtney’s 2003 overdose), and having an “alter ego” named Cherry Kookoo, Frances Bean appears to be relatively stable. In 2008 she became an intern at Rolling Stone, following in Hirschberg’s footsteps.


#73: Eminem’s Relationship With Kim

Unlike most rappers, Eminem has never felt the need to pretend his romantic life consists solely of anonymous sex with an ever-growing stable of hoes. The megastar has been a one-woman man for most his life, and he’s not afraid to say her name: Kim. He’s also not afraid to brutally murder her in song and beat a blow-up doll of her on stage. What can you say? He’s a heart-on-his-sleeve kind of guy.

The couple first met as young teenagers in 1989, and had a daughter, Hailie Jade, five years later. But the couple didn’t marry until after the release of his breakthrough album, 1999’s The Slim Shady LP. Despite the album’s “’97 Bonnie & Clyde,” in which Eminem takes his daughter to a lake to help dump her mother’s dead body, Kim hoped marrying would keep him faithful on tour. It didn’t. But it wasn’t until after 2000’s “Kim,” a prequel to “Bonnie” which described his wife’s murder in gory detail (“bleed, bitch, bleed!”), that their family drama made headlines.

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