#10 Winona Ryder
According to actress Winona Ryder, she had simply forgotten to pay for thousands of dollars worth of merchandise stuffed in her purse when she was apprehended leaving a Saks Fifth Avenue store in Beverly Hills. Police disagreed. Ryder was convicted of grand theft and given three years probation.
#9 Chris Brown
Where once Ike and Tina ruled as the best known dysfunctional couple, along came Chris Brown and Rihanna – two budding pop stars who were wildly in love. So wild that on February 8, 2009 word came that the couple had come to blows. Then Brown turned himself into the police. Then the shocking photos of Rihanna’s bruised face. Then Brown was dropped from multiple sponsors. Finally, Brown was given five-years probation and community service before resuming his recording career.
#8 Hugh Grant
Hugh Grant was facing a public relations nightmare after being picked up in 1995 for soliciting a prostitute, Divine Brown, on Sunset Boulevard. For many stars, it might have been a career-ending incident. Instead, Grant appeared on NBC’s The Tonight Show with Jay Leno during the week of his arrest to talk about what happened. His career survived, and so did his relationship with actress Elizabeth Hurley – at least in the short term.
#7 Mike Tyson
After being humiliated two years earlier with a crushing defeat by Buster Douglass, February 10, 1992 saw Tyson sentenced to six years in prison for raping 18-year-old beauty pageant winner Desiree Washington. While some were shocked, many pointed to his admittedly rocky marriage to TV star Robin Givens who hinted that he beat her, as possible seeds of his destruction.
#6 R. Kelly
Rap star and record producer R. Kelly has had several hits since his debut in the early 1990s, including “I Believe I Can Fly.” However, his career and his freedom were jeopardized in 2002, when he was indicted on criminal charges in connection with a tape showing him engaged in sex with a 14-year-old girl. Kelly managed to beat the charges and was acquitted on all counts in 2008.
#5 Biggie Smalls
Just one year after his former friend and East Coast/West Coast rap rival Tupac was gunned down, Biggie Smalls (Christopher Wallace) met a similar fate. Just weeks before the superstar was to release his much-anticipated follow up album to his already classic Ready to Die, Biggie was shot to death at a stop light on March 9, 1997 in Los Angeles. Despite multiple lawsuits and questioned involvement from the police, Biggie’s murder has yet to be solved.
#4 Martha Stewart
Martha Stewart built an empire on a foundation of cooking, sewing, decorating and all-around good taste. But in 2004, she traded her designer duds in for an orange jumpsuit when she went to jail for insider trading. After serving five months, she launched a public relations campaign that reclaimed her status as one of the most powerful women in America.
#3 Tupac Shakur
On the night of September 7, 1996, Tupac met his grisly end after being gunned down in Las Vegas after a Mike Tyson fight. Suspicions grew as Tupac’s label-owner, and known thug, Suge Knight escaped with only a flesh wound while Tupac was hit several times. Throw in Tupac’s eerie mentions of his death on previous songs and an album that mentions the Illuminati, the rapper achieved ever-lasting Elvis status despite autopsy photos.
#2 Michael Jackson
Even during the Thriller days, we knew Michael was a bit odd. But in 2003, when he talked of sharing his bed with children during a prime-time interview, America gave Michael the collective side-eye. Soon, the King got popped for “lewd acts” with a child and was at the center of a highly-publicized trial that ran for the first six months of 2005. Ultimately, Michael was found “not guilty” though the stigma followed him to his death.
#1 O.J. Simpson
O.J. Simpson was tried on two counts of murder following the June 1994 deaths of his ex-wife Nicole Brown Simpson and her friend Ronald Goldman. The surprise finale of O.J. Simpson’s trial saw him go free; a decision that split audiences along color lines as centuries of racial injustice came bubbling up in break-rooms around the country. Sadly, what is often forgotten is that two people brutally lost their life and their killer has yet to be caught.