Born and raised in Chicago, Illinois, Kelly was into music at an early age. Kelly's mother, Joanne Kelly, was a singer herself and performed in a group called Six Pack. Kelly states that it was she who heavily influenced his interest in music early on. As a teenager, Kelly began street performing 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 MGM, 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. Internal disputes lead to a conflict between R. Kelly and MGM and decided to part ways. R. Kelly, with the help of manager Barry Hankerson, was able to get out of his contract with MGM. Hankerson then helped Kelly sign a deal with Jive Records in 1991.

Shortly after getting his record deal with Chris Anderson His Cousin, Kelly met Andre Boykins from Public Announcement and auditioned the guys to be his back up singers and dancers. R. Kelly & Public Announcement released their debut album, Born Into the '90s in January 1992. One of the last albums to be 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 was led by Kelly. The group was billed as R. Kelly and Public Announcement essentially making the group backup members for Kelly rather than in a cohesive unit. After a successful tour ended in 1993, Kelly left Public Announcement to focus on a solo career.

In 1993, Kelly's debut solo album, 12 Play, was released in the fall of that year 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. The single became the longest running number one R&B hit in over 30 years on the singles chart in Billboard magazine. Subsequent hit singles were released such as "Your Body's Callin'" and "Sex Me". 12 Play held the number on spot on Billboard's Top R&B Albums chart for nine consecutive weeks making Kelly one of the hottest, most sought after performers of the 90s in R&B and hip hop circles. Kelly's career really took off with the success of 12 Play and Kelly began outside work as a record producer working with notable acts such as Toni Braxton, the Winans, Gladys Knight, and Quincy Jones, and introducing urban audiences to young female singers such as Aaliyah and the duo Changing Faces. In 1994, 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 his 1995 album, HIStory. It was later determined by a Belgium right society called SABAM, that Kelly had plagiarized the melody for "You Are Not Alone" from the song's original 1993 composition by veteran songwriters-producers and publishers Eddy and Danny Van Passel. Kelly's solo success continued with the release of his second solo album, R. Kelly, popular for the singles "You Remind Me of Something" and "I Can't Sleep (Baby If I)". A duet with Ronald Isley of The Isley Brothers created a hit with "Down Low", partially due to the music video of the song which introduced fans to Isley's "Mr. Biggs" character.

In 1996, Kelly released one of his most successful singles with "I Believe I Can Fly", originally released on the Space Jam soundtrack. The single, which came up after the movie's star Michael Jordan asked Kelly to compose a song for the soundtrack, was composed while Kelly was on a tour with The Notorious B.I.G. "I Believe I Can Fly" reached No. 2 on the Billboard Hot 100, and No. 1 on the UK pop charts. The single was a huge worldwide success and remains Kelly's signature song. Rolling Stone Magazine named it as the 408th of its top 500 songs of all time. Building on the hype of "Fly", Kelly released a double album simply titled R. That album would become Kelly's biggest-selling album to date selling over eight million copies according to the RIAA and Soundscan and yielded the popular singles, "I'm Your Angel" (featuring Celine Dion) and "When a Woman's Fed Up". In between and afterwards, Kelly also found success with soundtracks such as "Gotham City" from Batman & Robin, "Bad Man" from Shaft and "The World's Greatest" from Ali. In 1999, Kelly also wrote and produced, along with Wyclef Jean, the majority of the soundtrack to the Eddie Murphy and Martin Lawrence movie Life. Kelly composed ten songs on the soundtrack while Wyclef composed five. Kelly also contributed two songs, Bad Man and Up and Outta Here, to the updated Samuel L. Jackson movie, Shaft. In 2000, Kelly released TP-2.com, which yielded the hits "I Wish" and the remix to "Fiesta", which included a collaboration with Jay-Z. Because of the success of that song and another Kelly/Jay-Z collaboration, "Guilty 'Til Proven Innocent", from Jay-Z's Dynasty album, it was announced in early 2002 that the duo collaborated on a joint album and tour titled The Best of Both Worlds. Due to controversy surrounding Kelly at the time, there was little promotion with the album when it was finally released and Kelly instead refocused his attention on his solo work as both a recording artist and producer.

During late 2001 and early 2002, Kelly began working on the follow up to his album TP-2.com entitled Loveland. The album was scheduled to be released in November 2002, but like Best of Both Worlds before it, heavy bootlegging led to it being delayed. The singer then retooled the whole album titled the Chocolate Factory did feature several of the bootlegged tracks - and many have cropped up elsewhere, as seen below. It also came as a six track bonus disc with the initial pressings of Chocolate Factory (Bootlegged tracks are listed in this footnote).

In early 2003, the album Chocolate Factory became a runaway success for Kelly, selling over three million copies due to the success of singles such as "Ignition", "Snake" and "Step in the Name of Love". Later that year Kelly followed that success by releasing his first, and long overdue, greatest hits collection The R in R&B Collection Volume 1. In 2004, Kelly released the ambitious two-disc set, Happy People/U Saved Me, with the former side including feel good stepping inspired tracks, while focusing on gospel and inspirational material on the latter. That same year, Kelly performed the Star-Spangled Banner during the introduction of the world championship boxing fight between Bernard Hopkins and Jermain Taylor. His performance, which included a line of dancers doing the "stepping" routine and a pre-recorded instrumental track set to the sound of "Happy People", was met with a mixed reaction. In October of 2004, Kelly reunited with Jay-Z to do a follow-up to their Best of Both Worlds album shortly after announcing a tour to coincide with the project after the duo performed together during Jay-Z's "farewell" concert at Madison Square Garden a year before. The duo's Unfinished Business album was released and peaked at number-one on the Billboard chart.

Double Up included the hit single "I'm a Flirt (Remix)", featuring T.I. and T-Pain. The original track entitled "I'm a Flirt", also produced and co-written by R. Kelly, appeared as a hidden track on Bow Wow's The Price of Fame (2006). However, Kelly never gave the rights for the song to be released as a formal single, although it was played by many radio stations before the remix version. Kelly's first single from 'Double Up' was "I'm a Flirt (Remix)." Bow Wow was not featured on this version of the song. In Kelly's video for "I'm a Flirt (Remix)", he encourages fans to call a number which flashes up quickly on the screen. Fans who called the number were greeted by a recording of Kelly talking about his upcoming album and playing snippets of new songs in the studio. "I'm a Flirt (Remix)" was successful for Kelly. The song peaked at number 12 on the Billboard Hot 100. It also reached number one on the Billboard Hot Rap Tracks. R Kelly is also set to release a hit with new English rapper Martin Rattigan. This was confirmed by both parties on September 16th 2008 and will feature on Rattigan's upcoming album Stickup. Another hit on the album, "Same Girl", was a duet between Kelly and Usher. The single peaked at number 20 on the Hot 100 and peaked at number four on the R&B chart. Other singles such as "Rock Star" - featuring Ludacris and Kid Rock, "Sex Planet" and "Freaky in the Club" were modest R&B charters. The latter two were not officially released as singles, neither was the title track featuring Snoop Dogg.

Kelly's other single from Double Up titled "Rise Up" was a tribute to the victims of the Virginia Tech massacre. The song was officially released as a digital download May 15, 2007. Proceeds were donated to the Hokie Spirit Memorial Fund, a fund that helped family members of the victims of the shootings. In 2008, Billboard reported that Kelly plans to release his newest album titled 12 Play: Fourth Quarter this summer. The album's current single, "Hair Braider", has climbed as high as No. 56 on Billboard's R&B chart so far. On September 18, Kelly released the video to the second single "Skin" from 4th Quarter. However, the album still has no official release date. A few months later, Kelly recorded a verse for a remix to Kanye West's single Love Lockdown. A recent track was leaked on the internet titled "I Believe", containing an excerpt from Barack Obamas presidential acceptance speech. This song is available on iTunes as a free download.