Inside R. Kelly's Most Shocking Scandals Over the Years, None of Which Derailed His Success in Any Perceivable Way
On Aug. 31, 1994, R. Kelly married Aaliyah at a hotel in Rosemont, Ill. He was 27. She was 15, but the marriage certificate falsely listed her age as 18. The union was annulled months later. At the 1994 Billboard Music Awards that December, R. Kelly called Aaliyah, whom he had first met when she was 12, his "best friend in the whole, wide world."
In 1998, R. Kelly won three Grammys for "I Believe I Can Fly," to date his most successful single. His questionable relationship with Aaliyah relegated to an asterisk at the time and not altogether widely known outside of the industry and hardcore R&B enthusiasts, the Recording Academy heartily rewarded the "Bump N Grind" singer for his Space Jam anthem—and continued to recognize him with 19 more nominations between then and 2015. Devoted fans continued to buy albums and go to concerts, while casual listeners popped in whenever a hit such as the infectious "Ignition (Remix)" or the much hyped "Trapped in the Closet" went mainstream. Fellow artists continued to sign up to collaborate, including Jay-Z, Jennifer Hudson, Justin Bieber and Lady Gaga.
If only that weird blip of a marriage, born of a premature connection they had in the studio while working on Aaliyah's 1994 debut album, Age Ain't Nothing But a Number, had been it.
But though the legal quagmires he's found himself in have largely panned out in his favor, R. Kelly has an increasingly disturbing history when it comes to allegations of misconduct with underage girls and women who claim he's more Svengali than smooth operator. A new round of allegations, including the latest that he paid a woman not to talk about having a relationship with him when she was underage (through his attorney he has firmly denied the claim as reported by Buzzfeed News), spotlights a sordid timeline that goes back more than 20 years.
A young woman named Tiffany Hawkins sued Kelly in 1996 for allegedly "engaging in inappropriate sexual contact," including "group sexual sexual intercourse with [her] and other minors" several years prior, when she was 15 and he was 24.
Hawkins was asking for at least $10 million in damages. Kelly immediately counter-sued for defamation; the Chicago Sun-Times reported that Kelly settled for $250,000 in 1998, though his attorney would only confirm that the two sides reached a confidential settlement. "I'm not trying to down him, because I honestly think it has to be a sickness," a friend of Hawkins, who had planned to testified on her behalf at trial, told the paper. "Looking at pictures of me and Tiffany when we were freshmen—boy, we were ugly little girls compared to what he could have had, so I didn't understand why he did what he did."
Also in 1996, Kelly married Andrea Lee, whom he'd first met in 1994—she was 20—when she auditioned to be a dancer on his 12 Play Tour. He and Lee would go on to have three children together, Joann, Jay and Robert Jr., before separating in 2005 and divorcing in 2009.
It was a December 2000 report in the Chicago Sun-Times that first detailed Hawkins' lawsuit and the full legal story of what happened with Aaliyah, as well as revealed that Kelly had twice been under criminal investigation for allegedly having sex with an underage girl. Both investigations ended when the girl wouldn't cooperate. As far as Aaliyah stood, "When R. Kelly comes up, she doesn't even speak his name, and nobody's allowed to ask about it at all," a rep for Virgin Records told the paper.
Tracey Sampson, who claimed she had a 10-month relationship with Kelly that started in May 2000 when she was 17 and working as an intern at Epic Records, sued the singer in 2001 for $50,000.
In February 2002, an anonymous tipster sent an almost 27-minute tape to Jim DeRogatis at the Sun-Times which appeared to show Kelly having sex with a very young woman.
Days later, Kelly performed at the 2002 Winter Olympics Opening Ceremony in Salt Lake City while Chicago police investigated.
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