Now the R&B singer faces a trial in his hometown of Chicago on charges accusing him of rigging his 2008 child pornography trial and of enticing minors for sex.
The trial comes after he was sentenced in June in federal court in New York to three decades behind bars on sex trafficking charges.
While Kelly, born Robert Sylvester Kelly, has vehemently denied the allegations, his accusers testified that he subjected them to perverse and sadistic whims when they were underage.
A timeline of Kelly’s life through his rise and fall as an R&B artist:
1990: R. Kelly’s R&B group MGM wins the US$100,000 (NZ$157,000) grand prize on the syndicated television talent show Big Break, hosted by Natalie Cole. Because of money disagreements, that is the last time the group performed.
January 1992: R. Kelly & Public Announcement debuts Born Into The ’90s. Released a year later, the album goes platinum.
November 1993: His album 12 Play is released and eventually sells more than 5 million copies. Hit singles include Sex Me and Bump N’ Grind, which became the longest-running No. 1 R&B song in more than 30 years.
August 31, 1994: At age 27, R. Kelly marries 15-year-old R&B singer Aaliyah D Haughton in a secret ceremony arranged by Kelly at a hotel in Chicago. The marriage is annulled months later because of Aaliyah’s age. (Aaliyah died in a plane crash seven years later, at age 22.)
November 1996: R. Kelly releases his third album, R. Kelly. A month later, he incorporates Rockland Records. His song I Believe I Can Fly, from the Space Jam soundtrack, peaks at No. 2 on the Billboard pop chart. The same year, he marries 22-year-old Andrea Lee, a dancer from his touring troupe. The couple goes on to have three children: Joanne, Jaya and Robert Jr.
February 1998: Kelly wins three Grammys for I Believe I Can Fly.
August 2001: Tracy Sampson files a lawsuit against Kelly, alleging their sex was illegal under Illinois law because he was in “a position of authority over her.” The case was reportedly settled out of court for an undisclosed amount.
February 8, 2002: The Chicago Sun-Times reports that it received a videotape allegedly showing Kelly having sex with a minor. The paper reported Chicago police began investigating allegations about Kelly and the same girl three years earlier. At the time, the girl and her parents deny she was having sex with Kelly.
June 5, 2002: Kelly is indicted in Chicago on child pornography charges stemming from the sex tape. He pleads not guilty and is released on $750,000 bail.
May 9, 2008: Kelly’s child pornography trial begins.
June 13, 2008: Kelly is acquitted on all counts after less than a full day of deliberations.
June 27, 2012: Kelly publishes his autobiography, Soulacoaster: The Diary of Me, focusing on his creative and family life rather than his legal troubles.
September 29, 2012: Kelly is nominated for two Soul Train Awards, making him the most nominated act ever at the awards show.
July 17, 2017: BuzzFeed reports on parents’ claims that Kelly brainwashed their daughters and was keeping them in an abusive cult. One woman says she was with Kelly willingly. Activists launched the #MuteRKelly movement, calling for boycotts of his music.
May 2018: Spotify cuts R. Kelly’s music from its playlists, citing its policy on hate content and hateful conduct. Shortly after, Apple and Pandora also stop promoting his music. Kelly’s team pushes back, noting other artists on Spotify had been accused or convicted of crimes.
January 3, 2019: Lifetime airs the documentary Surviving R. Kelly, which revisited old allegations against him and brought new ones into the spotlight. The series followed the BBC’s R Kelly: Sex, Girls & Videotapes, released the previous year, that alleged the singer was holding women against their will.
January 21, 2019: Multiple media outlets report that Kelly and his label, Sony subsidiary RCA Records, part ways. Kelly continues to deny all allegations of sexual misconduct.
February 22, 2019: Kelly is arrested and charged with 10 counts of aggravated sexual abuse.
March 6, 2019: CBS airs interview in which Kelly vehemently denies the sexual abuse charges. Later, authorities in Cook County take Kelly into custody after he tells a judge he couldn’t pay $161,000 in back child support he owed his children’s mother.
May 30, 2019: Kelly is charged with 11 new sex-related counts in Chicago. They involve one of the women who accused him of sexually abusing her when she was underage.
July 11, 2019: Kelly is indicted by a federal grand jury in Chicago on charges including child pornography, enticement of a minor and obstruction of justice. A separate indictment filed in the Eastern District of New York included charges of racketeering, kidnapping, forced labour and the sexual exploitation of a child. He is again arrested in Chicago.
July 16, 2019: A federal judge orders Kelly held without bond after a prosecutor warns he poses an extreme danger to young girls.
August 5, 2019: Kelly is charged in Minnesota with prostitution and solicitation related to an allegation that he invited a 17-year-old girl to his hotel room in 2001 and paid her $200 to dance naked with him.
March 5, 2020: Kelly pleads not guilty in Chicago to an updated federal indictment that included child pornography charges and allegations involving a new accuser.
August 12, 2020: Federal prosecutors announce charges against three men accused of threatening and intimidating women who have accused Kelly of abuse, including one man suspected of setting fire to a vehicle in Florida.
August 18, 2021: Opening statements begin in Kelly’s federal trial in New York.
September 27, 2021: A jury finds Kelly guilty of sex trafficking and violating the Mann Act, which makes it illegal to take anyone across state lines “for any immoral purpose.”
June 29, 2022: Kelly is sentenced to 30 years in prison in the New York case.
August 15, 2022: Jury selection starts for Kelly in federal court in Chicago on child pornography and obstruction of justice charges.