Jermaine is the owner of So So Def Records, a label that has signed such hip hop and R&B artists as Da Brat, Jagged Edge, and Xscape; as well as younger artists, Kris Kross and Bow Wow, for whom Jermaine has ghostwritten songs. In 2004, Jermaine was appointed Executive Vice President of Urban Music at Virgin Records and moved So So Def to Virgin. Jermaine’s other business ventures include Chicago-based distillery 3 Vodka and his boutique restaurant, Cafe Dupri.

In 1998 Jermaine released his own debut album, Jermaine Dupri Presents Life In 1472. The album went platinum and included such hits as "Money Ain't A Thang" and "The Party Continues." Jermaine collaborated with several other artists on his debut album, including Jay-Z on "Money Ain’t a Thing;" Mariah Carey on "Sweetheart;" and Snoop Dogg and Warren G on "Protector's of 1472." In 2005, Jermaine released Young, Fly & Flashy, Vol. 1, a collection of tracks produced by and featuring Jermaine. The video for the album’s track "Gotta Getcha" features Singer Janet Jackson, whom Jermaine also collaborated with for her album 20 Years Old, released in September of 2006.

In 2002, Jermaine incited producer Dr Dre by claiming in an interview to do more complete production work on albums. Dr. Dre hit back at Jermaine in the song "Say What You Say" from Eminem’s album, The Eminem Show. Jermaine then retaliated by leaking an "underground track" on the Internet called "JD's Reply." In the lyrics he refers to Dr. Dre as a "gayass mark." At the end of the track, he threatens, "If you come at me again, I'm gonna come back at you three times harder."

Jermaine has attempted to subvert the present-day image of hip hop music, stating: "Everybody's got to stop acting like they wear bandanas all day, every day.... You've got to face the facts that you do sit on the phone sometimes and try to talk to a girl for hours. Everybody's done that, even the hardest of thugs. I think it's appropriate on my album because I'm talking about so much wealth that I needed to let people know that life ain't shit if you can't share it with somebody. To have a fly life like I've got, it's important to have somebody to share it with."

Jermaine is currently in a relationship with fellow music veteran Janet Jackson. The couple is rumored to be secretly married; a rumor fueled by reports that movie-maker Brett Ratner refers to Jermaine as a "married man" in a documentary. Jermaine is also rumored to be collaborating with Janet’s brother, embattled pop singer Michael Jackson, on Michael’s next album.

YUDDY