#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.

Winona Ryder [Adrees Latif/Pool/Getty Images]

Winona Ryder [Jonathan Alcorn/Pool/Getty Images]

Winona Ryder [Steve Grayson-Pool/Getty Images]

Winona Ryder [Frazer Harrison/Getty Images]

Winona Ryder [Mel Bouzad/Getty Images]

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 voicemail 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 described so bluntly 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!

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: a 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.

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!”

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]

Mick Jagger & Marianne Faithfull [Central Press/Hulton Archive/Getty Images]

Mick Jagger & Marianne Faithfull [Evening Standard/Getty Images]

Marianne Faithfull & Mick Jagger [Hulton Archive/Getty Images]

Mick Jagger & Marianne Faithfull [William Lovelace/Express/Getty Images]

Here’s a sure-fire way to get rich and famous: F*ck a D-List singer (Ray-J) with a famous big sister (Brandy) and capture it on videotape. If you have a big round ass like Kim Kardashian, you could ride what should be 15 seconds of notoriety into a full-blown Hollywood career.

Kim sued Vivid Video (who bought the sultry film for $1 million from a third party) for releasing her “private” tape of dirty sex (water sports, anyone?). But where would Kim be without her porn video? Not on gossip blogs and entertainment websites. Not getting paid to shake her ass at club parties. Not dating NFL stud Reggie Bush. And not making serious bank off her own E! reality TV show.

Kim has sworn that she will “never, never, never again” film herself getting freaky, but we’re begging her to never say never—at least not to the Record button being pressed in the bedroom. For the sake of her ratings, this girl needs to keep her options—and legs—open.

From Kim Kardashian Superstar, with Ray J.

From Kim Kardashian Superstar, with Ray J.

From Kim Kardashian Superstar, with Ray J.

Kim Kardashian [Charley Gallay/Getty Images]

Ray-J [Donna Ward/Getty Images]

Kim Kardashian [Pascal Le Segretain/Getty Images]

Ray-J [Donna Ward/Getty Images]

Kim Kardashian [Neilson Barnard/Getty Images]

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.

It’s not like Liza Minnelli had a great reputation before she walked down the aisle with dough-faced David Gest in March 2002. The Oscar-winning daughter of legend (and legendary mess) Judy Garland spent much of the eighties staring at the walls of rehab facilities, to no avail. Liza’s other addiction—husbands—reached a new low when she married David, a concert promoter turned Minnelli manager, best known for his f*cked-up face (courtesy of Michael Jackson’s plastic surgeon) and the rumors swirling around his sexual orientation.

Their wedding was a D-list celebrity clusterf*ck, with Jackson and Elizabeth Taylor serving as the wedding party and the bride allegedly zonked out on pills. During the vows, Gest declared, “You are everything to me and I will love you forever,” before grabbing and kissing her like “a drowning man eating a watermelon” (one guest’s description). The newlyweds dived into a VH1 reality show, but production was halted after just one episode due to Gest being a crazy asshole, canceling shoots and restricting access to Liza. Their 2003 divorce was fuglier than their botched plastic surgeries. David sued his lady love for $10 million, alleging she’d beaten him so badly while drunk that he was hospitalized with nerve damage–and that she’d knowingly given him herpes. What a wedding present! Liza countersued, claiming David was an obsessive cleaner who tried to poison her and stole over $2 million of her cash. The divorce wasn’t settled until 2007.

Gest followed their marital flop with a slew of appearances on UK reality shows, while Minnelli has had a bit more success in the States with appearances on Law & Order and Arrested Development.

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 Brooks’ Robin 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.”

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.”

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 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.