[6] Kelly's career ended in 2019 following his arrest and subsequent convictions on federal racketeering and sex trafficking charges involving sexual abuse of minors.

Kelly received a Grammy Award nomination for his contributions to Jackson's 1995 single, "You Are Not Alone", which earned a Guinness World Record as the first song to debut atop the Billboard Hot 100 in the chart's history.

Renewed interest in the allegations resulted in additional investigations by law enforcement beginning in 2019, which led to multiple indictments and Kelly's arrest.

[13][22] Kelly's younger brother, Carey, stated that he suffered from years of sexual abuse at the hands of their older sister, Theresa, who was entrusted with babysitting the siblings.

[23][24] Carey stated that although their older brother, Bruce, was spared and allowed to play outside, both he and Kelly were punished at separate times indoors by Theresa, who refused to acknowledge the abuse when confronted years later.

[41] Kelly gained national recognition when MGM participated on the talent TV show Big Break, hosted by Natalie Cole.

The album, released during the new jack swing period of the early 1990s, yielded the R&B hits "She's Got That Vibe", "Honey Love", "Dedicated", and "Slow Dance (Hey Mr. DJ)", with Kelly singing lead vocals.

Kelly's first solo album, 12 Play, was released on November 9, 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 Billboard Hot R&B Singles chart.

[56] Kelly said "I love basketball enough to not totally let go of my music, but just put it to the side for a minute and fulfill some dreams of mine that I've had for a long time.

In addition to producing and writing the project, Kelly made vocal contribution to the hit duet "Be Careful", which became a serious factor as to why the album was certified platinum in December 2000.

[63] In the summer of 1999, he wrote and produced a majority of the soundtrack to the Martin Lawrence and Eddie Murphy film, Life, which features tracks from K-Ci & JoJo, Maxwell, Mýa, and Destiny's Child, among others.

AllMusic's Jason Birchmeier gave TP-2.com 4 stars and stated: "Kelly knows how to take proven formulas and funnel them through his own stylistic aesthetic, which usually means slowing down the tempo, laying on lush choruses of strings and background vocals, taming down the lyrics for radio, and catering his pitch primarily to wistful women.

[69] MTV's Shaheem Reid wrote: "And if Jay and Kelly can put their egos to the side long enough to wrap up and promote their album, then their labels—Def Jam and Jive, respectively—can surely figure out a way to join forces and make cheddar together.

[70][71] Following a leak of the joint album on February 22, 2002, Roc-A-Fella and Jive moved the release date one week earlier in an effort to curtail piracy.

[115] In an interview in the September 2010 issue of XXL magazine, Kelly said he was working on three new albums (Epic, Love Letter, and Zodiac) which he described as "remixing himself".

[133] In 2012, Kelly made a series of announcements including a follow-up to the Love Letter album titled Write Me Back, which was released on June 26 to little fanfare,[134] as well as a third installment of Trapped in the Closet[135] and The Single Ladies Tour featuring R&B singer, Tamia.

On June 30, 2013, R. Kelly performed live at BET Awards Show singing hits as well as his new track "My Story" featuring Atlanta rapper 2 Chainz.

[141] Writing for New York magazine, David Marchese stated that Black Panties "was like a dare to the world: After all that he'd been accused of, after avoiding conviction, could R. Kelly still get away with making sex-obsessed music?

[142] Kelly co-wrote and sang on Lady Gaga's song "Do What U Want" from her 2013 album Artpop, performing the duet with her on Saturday Night Live on November 16, 2013,[146] and at the 2013 American Music Awards.

[147][30] "Do What U Want" had since been removed from streaming services and re-releases of Gaga's Artpop album following sexual misconduct allegations against Kelly in early 2019.

[157] In November 2015, Kelly released "Switch Up" featuring fellow Chicagoan Jeremih and Lil Wayne, followed by "Wake Up Everybody", "Marching Band" and "Backyard Party".

[159] On March 17, Pitbull released the song "Dedicated" off his album Climate Change and features guest appearances from American singers R. Kelly and Austin Mahone.

[166][167] Many outlets compared the song to that of his "Heaven I Need a Hug" extended version, Trapped in the Closet opera, "I Believe I Can Fly" concert remix, and O. J. Simpson's autobiographical novel If I Did It.

[20] While Kelly created a smooth, professional mixture of hip-hop beats, soulman crooning and funk, the most distinctive element of his music is its explicit sensuality.

"Sex Me", "Bump n' Grind", "Your Body's Callin'", and "Feelin' on Yo Booty" are considered to be examples, as their productions were seductive enough to sell such blatant come-ons.

[46] Writing for the New York Daily News in 1997, Nunyo Demasio stated "With a voice that easily shifts from booming baritone to seductive alto, Kelly has gained international celebrity by combining streetwise rhythms with sexually explicit lyrics.

Chicago Sun-Times reporters Jim DeRogatis and Abdon Pallasch observed about the contrasting themes: "... the image he liked to project was that of the "R&B Thug"... bringing the streetwise persona of the gangsta rapper into the more polite world of R&B.

[177] DeRogatis and Pallasch reported that at concerts where Kelly would go from singing "Like a Real Freak" to "I Wish": "Many fans found these abrupt shifts between the transcendent and the venal, the inspirational and the X-rated jarring.

[179][180] In addition to his solo and collaboration success, Kelly has also written and produced several hit songs, such as "Age Ain't Nothing but a Number" for Aaliyah, "Fortunate" for Maxwell, "You Are Not Alone" for Michael Jackson, "G.H.E.T.T.O.U.T."

[191] On July 30, 2024, multiple news outlets reported that Kelly, alongside his lawyer Jennifer Bonjean, had asked the Supreme Court to review his child pornography case, which could potentially drop 20 years off his sentence.