One of the most popular artists during a period lasting from the early '90s into the mid-2010s, contemporary R&B singer, songwriter, and producer R. Kelly picked up where new jack swing left off by developing his own mix of soul, funk, hip-hop, and gospel. Fourteen of Kelly's studio albums reached in the Top Ten of the Billboard 200, a count that includes the RIAA-certified multi-platinum sets 12 Play (1993), R. (1998), and TP-2.com (2000), as well as Chocolate Factory (2003) and Happy People/U Saved Me (2004). Among Kelly's Top Ten pop singles are the Hot 100-topping "Bump N' Grind," the Grammy-winning "I Believe I Can Fly," and the remixes of "Step in the Name of Love" and "Ignition." He was also behind Top Ten hits by the likes of Aaliyah and Michael Jackson. Kelly was arrested on federal sex crime charges in 2019, and was convicted two years later on nine counts of sex trafficking and racketeering. He received a 30-year prison sentence in 2022.

Born Robert Sylvester Kelly on January 8, 1967, in Chicago, R. Kelly grew up singing in the Baptist church choir in which his mother sang lead. After he won a high school talent show, Kelly decided to concentrate on music. He dropped out of school and formed MGM (Musically Gifted Men), a vocal group that in 1989 won the grand prize on the syndicated talent competition Big Break. MGM released the single "Why You Wanna Play Me" in 1990, but Kelly disbanded the group within a year and teamed with Public Announcement. R. Kelly and Public Announcement released their debut album, Born into the '90s, in 1992. The singles "Honey Love" and "Slow Dance (Hey Mr. DJ)" were number one R&B/hip-hop hits, while "Dedicated" was the album's biggest pop hit, a Top 40 single.

Kelly went solo in 1993 with 12 Play, an album that contained the number one pop hit "Bump N' Grind," reached number two on the Billboard 200, and eventually went platinum six times over. 12 Play was followed within six months by Age Ain't Nothing But a Number, the Kelly-produced 1994 debut from Aaliyah. Kelly and Aaliyah wed in secret that August. Aaliyah's parents sought an annulment based on their daughter's age (the marriage certificate stated she was 18, three years older than her actual age), which was granted in February 1995. Later that year, Michael Jackson released "You Are Not Alone," a ballad Kelly wrote and co-produced. It became Jackson's last number one hit and earned Kelly his first Grammy nominations. Kelly's eponymous second album was also out that year. R. Kelly topped the Billboard 200, spawned a trio of Top Ten singles, and went quintuple platinum. Between full-lengths, he further consolidated his crossover success with soundtrack work. "I Believe I Can Fly," a gospel-inspired ballad for the 1996 film Space Jam, peaked at number two on the Hot 100, and won Grammy Awards for Best R&B Song, Best Male R&B Vocal Performance, and Best Song Written Specifically for a Motion Picture or for Television. The Batman Robin soundtrack single "Gotham City" took Kelly back to the Top Ten in 1997.

Released in 1998, the double-disc R. entered the Billboard 200 at number two and became Kelly's highest-certified album, platinum eight times over (based on the RIAA counting each shipped copy as two units). Its first single, the Celine Dion duet "I'm Your Angel," topped the Hot 100. Kelly returned in 2000 with the chart-topping TP-2.com, the biggest single of which was the number six pop hit "Fiesta [Remix]," featuring Jay-Z and Boo Gotti. Kelly and Jay-Z then paired up for the 2002 album The Best of Both Worlds. Weeks before the record's release, The Chicago Sun-Times reported that it had received a videotape showing Kelly having sex with a 14-year-old girl. After the story broke, reports surfaced that Kelly had settled a civil suit (four years earlier) involving a sexual relationship with a then-underage girl, and that he was in the process of settling another suit making similar allegations. He subsequently settled the latter suit and faced numerous additional suits. That June, Kelly was charged with 21 counts of child pornography and related offenses. He pleaded not guilty and responded with the single "Heaven, I Need a Hug." "Ignition [Remix]" followed before the end of the year and narrowly missed the top of the Hot 100.

During 2003 and 2004, Kelly released the number one album Chocolate Factory and the number two double-disc Happy People/U Saved Me. "Ignition [Remix]" led the former, which yielded a second Top Ten hit with "Step in the Name of Love [Remix]." Kelly and Jay-Z also released their second album as a duo, Unfinished Business, which trumped their first one together by entering the Billboard 200 at the top. TP.3 Reloaded and Double Up, issued respectively in 2005 and 2007, lengthened Kelly's run of number one full-lengths; the first of these two albums included the first five (of 33) chapters in Kelly's "Trapped in the Closet" series. Kelly was acquitted in 2008 of the child pornography charges he faced six years earlier. He closed out the decade the next year with the number four Billboard 200 entry Untitled, his ninth album.

Kelly entered the 2010s with Epic, a descriptively titled compilation that combined previously released material with new recordings such as "Sign of a Victory," written for the opening ceremony of the 2010 FIFA World Cup. A couple months after that, Kelly offered his tenth proper album, Love Letter. He underwent emergency throat surgery in 2011 and the next year published a memoir, The Soulacoaster: The Diary of Me (written with David Ritz), as well as another album, Write Me Back. Kelly's streak of Top Ten albums was extended to 14 with Black Panties, issued in 2013, and ended when The Buffet peaked at number 16 in 2015. His first holiday release, 12 Nights of Christmas, followed in 2016.

In 2017, Jim DeRogatis, the journalist who broke the R. Kelly sex abuse story published 15 years earlier by The Chicago Sun-Times, reported for BuzzFeed News that three families accused Kelly of keeping their daughters hostage in a cult. Over the next two years, these accusations expanded through reports at the BBC and in The Washington Post, and culminated in the Lifetime documentary series Surviving R. Kelly. A month after the January 2019 airing of Surviving R. Kelly, Kelly was charged with ten counts of aggravated criminal sexual abuse. He was indicted on 18 counts that July, and went to trial in August facing nine counts, including kidnapping, sexual exploitation of a child, sex trafficking, racketeering, and bribery. A federal jury found Kelly guilty on all nine counts. In June 2022, he was sentenced to 30 years in prison. ~ TiVo Staff, Rovi