After growing up in poor circumstances in Chicago and singing on trains for pocket change, his career took off in 1991, eventually leading to both Grammy Award and platinum albums. His best known song is the ballad "I Believe I Can Fly". Some of his rap texts have been criticized for their sexual subject matter, but other songs are close to gospel and in fact Kelly has confirmed that he has "found God".
In 1994, Kelly briefly married the then 15-year-old singer Aaliyah, who died in a plane crash in 2001.
In recent years, Kelly has fought or settled several civil lawsuits alleging coerced or underage sexual relationships. Because of this, many radio stations in the United States have refused to play his music.
Kelly has been accused of and investigated for having had a sexual relationship with a 14-year-old daughter of an associate; this accusation gained force with a video tape that was sent anonymously to a Chicago newspaper in February 2002 and allegedly shows R. Kelly having sex with the girl. While witnesses have identified Kelly and the girl, the girl herself and her parents have denied that she is shown on the tape. Bootleg copies of the tape are widely available on the black market. The tape shows seven sex acts, and in June 2002, Kelly was indicted in Chicago for seven counts of soliciting a minor for child pornography, seven counts of videotaping the acts, and seven counts of producing child pornography. The judge has decided that Kelly can travel in February 2004 to Los Angeles to attend the Grammy Awards, but also that he cannot associate with Michael Jackson.
In addition, Kelly was indicted in Florida in January 2003 on 12 counts of possession of child pornography. However, the charges were dropped after the search which led to the indictment was ruled illegal.
In 2003, Dave Chappelle made a skit showing R. Kelly pouring his pee and "Doo-Doo" Butter on teenage girls. It was very funny, but offended the real R. Kelly.