Before continuing his artistic career, Dupri opened a small store, "Rap Corna Guuds". He later formed the teen duo Kris Kross (Chris Kelly and Chris Smith) after meeting the boys at a local mall in 1991. The group's first album, Totally Krossed Out, was released in 1992 and went multi-platinum due to their singles "Jump" and "It's a Shame". He established his own record label called So So Def Recordings in 1993. Shortly after he discovered female R&B group Xscape at a festival in Atlanta and signed them to the newly minted label. Hummin' Comin' at 'Cha and went platinum. During the same year, on Yo! MTV Raps he met Chicago rapper Shawntae Harris, A.K.A. Da Brat through Kris Kross, signed her to his label So So Def Recordings, and released her debut Funkdafied (1994) which went Platinum. His finances were not hindered by a distribution deal made with Columbia Records in 1993.
In 1998, Jermaine Dupri surpassed all of his prior commercial ventures with his involvement in the release of Destiny's Child's eponymous debut album. Dupri renewed the focus on his own music career and released The Party Continues, the lead single from his debut studio album Jermaine Dupri Presents Life In 1472: The Original Soundtrack. Also that year he met Lil Bow Wow and signed him to So So Def Recordings. The two would later part ways but continued to collaborate on later projects. The deal with Columbia was terminated in 2002, and in 2003 Dupri switched to Arista Records. Jermaine worked on Mariah Carey's Christmas album, Merry Christmas II You, as well as with Weezer and Lil Wayne on the song "Can't Stop Partying." He also collaborated with DJ Chuckie to make a vocal version of the song Let The Bass Kick.
He contributed to most of Mariah Carey's albums, including her career comeback album, 2005's The Emancipation Of Mimi with the smash hit "We Belong Together", which stayed at number one for fourteen non-consecutive weeks, becoming the second longest running number one song in US chart history, behind Carey's 1996 collaboration with Boyz II Men on "One Sweet Day". He has also been a big contribution to R&B Pop singer Usher's career, producing most of his top hits on his albums My Way and 8701.