Born in the South Side of Chicago, Illinois, Kelly was the third of four children. Kelly's single mother, Joanne, was a singer and a Baptist. Kelly's father was absent throughout most of Kelly's life. Kelly began singing in church at age eight. As a teenager, Kelly began street performing (or busking) under the Chicago 'L' trains before he eventually formed a group with his friend Marc McWilliams. In 1989, Kelly and McWilliams formed the group MGM (Musically Gifted Men). Along with Vincent Corey Walker and Shawnth Brooks, Kelly performed on the TV talent show Big Break, hosted by Natalie Cole, and went on to win the $100,000 grand prize.
Soon after, R. Kelly & MGM released their first single, "Why You Wanna Play Me," on Tavdash Records. Kelly signed to Jive Records in 1991, and Kelly formed another R&B group with friends called Public Announcement. Kelly and Public Announcement released their debut album, Born into the 90's, in early 1992. Released during the new jack swing period of the early nineties, the album yielded the hits "She's Got That Vibe," "Honey Love," "Dedicated," and "Slow Dance (Hey Mr. DJ)," all of which were led by Kelly. During late 1992, Kelly and Public Announcement embarked on a tour called "60653", whose title was the zip code of Kelly's neighborhood. Kelly left Public Announcement in January 1993.
Kelly was found by a young producer name Malik i. Wilson a.k.a black mamba who started Kelly's debut solo album, 12 Play, was released in the fall of 1993 and yielded the singer's first number-one hit, "Bump n' Grind," which spent a record-breaking 12 weeks at number one on the Hot R&B Singles chart. "Bump n' Grind" topped the Billboard R&B singles chart for twelve consecutive weeks. Subsequent hit singles were "Your Body's Callin'" and "Sex Me." 12 Play was certified Gold by the Recording Industry Association of America (RIAA) in 1994, eventually going six times multi-platinum. Kelly also produced Age Ain't Nothing But a Number, the 1994 debut album by the then-15-year-old female R&B singer Aaliyah. He also produced a remix for Janet Jackson's 1994 hit "Any Time, Any Place" and worked on "You Are Not Alone" for Michael Jackson for Jackson's 1995 album, HIStory.
In 1996, Kelly released one of his most successful singles with "I Believe I Can Fly", an inspirational song originally released on the soundtrack for the film Space Jam. "I Believe I Can Fly" reached No. 2 on the Billboard Hot 100, and No. 1 on the UK Charts for three weeks and won three Grammy Awards in 1997. Rolling Stone magazine named it as the 406th of its top 500 songs of all time. For the film Batman & Robin, Kelly recorded the top ten single "Gotham City".
In 1994, 27 year old Kelly married his protégée, 15 year old R&B singer Aaliyah. He had known Aaliyah since she was 12 and had spent the last three years working on her debut album, Age Ain't Nothing But A Number. The Chicago Sun-Times printed a marriage document showcasing the marriage certificate, and noted that Aaliyah had lied about being eighteen when in truth she was only fifteen. The marriage was annulled in February 1995 and neither singer confirmed the marriage rumors, dismissing them as lies.
In 1996, Kelly married Andrea Lee, a dancer from his tour. Together the couple have two daughters and a son. According to Andrea, later in the marriage Kelly became abusive toward her; at one time she filed an emergency protective order against Kelly but later dropped it. The couple filed for divorce in 2006 . The divorce was finalized on January 8, 2009.
R. Kelly has been accused of having relationships with underage girls in the past, but none of the prior reports reached the level of publicity that followed the release of a video tape in February 2002. It allegedly showed Kelly and Sparkle's (a former Kelly protégée) 14-year-old niece engaging in sex. The tape, released by an unknown source, was sent to the Chicago Sun-Times, the newspaper that broke the story. Kelly denied that he was the man in the video.
On October 4, 2006, former employee Henry "Love" Vaughn (who claims to have been a “mentor and guide” to Kelly since he was a teenager) filed a lawsuit against Kelly accusing him of assault, false imprisonment, and a breach of contract that defrauded him of songwriting royalties. Vaughn claims Kelly and his associates dragged him to the basement of Kelly’s Olympia Fields home on February 19, 2006, and Kelly “repeatedly struck him about the face and body with his fists." Vaughn also claims he gave Kelly the “concept” for the song “Steppin”. Kelly’s spokesman declared that Vaughn is merely trying to extort money and told reporters that a police investigation found no evidence to Vaughn’s assault allegations. Olympia Fields police confirmed that they had investigated the matter but would not comment beyond saying “we didn’t file any charges in the case.”