The album included chapters of "Trapped in the Closet".On 2006, Kelly started The Light It Up Tour, It later became his first concert DVD. The original track entitled "I'm a Flirt", also produced and co-written by R.

A fast-moving current swept her away while she screamed Kelly's name. Kelly calls Lulu his very first musical inspiration. In January 2000, Kelly had won Favorite Male Soul/R&B Artist at the American Music Awards and, in February, was nominated for several Grammy Awards, including Best Male R&B Vocal Performance ("When a Woman's Fed Up"), Best R&B Album (R.), and Best Rap Performance by a Duo or Group ("Satisfy You") with P. On November 7, 2000, Kelly released his fifth studio album TP-2.com, an album harking back to his breakthrough album, 12 Play. You take parts of your life and you put it on these records and then for it to just be traded and moved around [is frustrating].

Kelly entered Kenwood Academy in Chicago's Hyde Park neighborhood in the fall of 1981, where he met his music teacher Lena Mc Lin, who encouraged Kelly to perform the Stevie Wonder classic "Ribbon in the Sky" in a high school talent show. Unlike Kelly's previous effort, R., all songs on TP-2was written, arranged, and produced entirely by Kelly. Instead Kelly re-recorded the entire album, titled it Chocolate Factory and featured several of the bootlegged tracks on the bonus Loveland disc.

In 2004, Kelly released the ambitious two-disc set Happy People/U Saved Me, with the first disc including feel-good, stepping-inspired tracks, while focusing on gospel and inspirational material on the second disc.

That same year, Kelly performed The Star-Spangled Banner during the introduction of the world championship boxing fight between Bernard Hopkins and Jermain Taylor.

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.

In 1996, Kelly was nominated for a Grammy for writing Michael Jackson's song "You Are Not Alone". The Recording Industry Association of America (RIAA) has recognized R. He remixed his own songs, Bump N' Grind, Sex Me and "Homie Lover Friend", a remix featured on the A Low Down Dirty Shame (soundtrack) along with Aaliyah's song, "The Thing I Like" which was written and produced by Kelly, as well. In 2000, Sparkle went Platinum due to the success of the first single,"Be Careful", a duet featuring R. Since the success of Space Jam's "I Believe I Can Fly", Kelly gained further fame for penning songs to popular soundtracks such as Batman & Robin ("Gotham City") and Life ("Fortunate").

In 20, Kelly released collaboration albums with rapper Jay-Z and has been a guest vocalist for other hip hop artists like Nas, Sean Combs, and The Notorious B. Kelly as one of the best-selling music artists in the United States with 40 million albums sold as well as only the fifth black artist to crack the top 50 of the same list. Kelly remixed songs for other artists including Aaliyah, Barry White, and Toni Braxton. On November 17, 1998, Kelly released his fourth studio album and first double album, R.

Kelly became the first musician to play professional basketball, when he was signed in 1997. "If Whitney Houston needs a song written", Gross said, "he would be able to leave the team to do that and come back".