Wingo was a late addition to the group, added after a recommendation from Kandi Burruss of Xscape. Burruss was also the one who brought the group to the attention of Dupri, who signed them to his Columbia Records distributed imprint, So So Def Recordings. The name Jagged Edge is derived from the song "Snakes" by rapper Ol' Dirty Bastard's debut album Return to the 36 Chambers: The Dirty Version, more specifically, the beginning of RZA's verse, which states, "Jagged Edge, Rockhead God, hard as Stonehenge..."
Jagged Edge began their mainstream recording career with the single "The Way That You Talk". They followed this in 1997 with the album, A Jagged Era which went gold, featuring the singles "I Gotta Be" and "The Way That You Talk". "I Gotta Be" which was written by the twins, reached number 11 on the R&B charts and number 23 on the Hot 100.
Following up on their debut album, Jagged Edge released J.E. Heartbreak in 1999. The album was the group's breakthrough album with several popular singles. The album went double platinum and had the hit single "Let's Get Married" which topped the R&B charts and reached number 11 on the Hot 100. The album's second single, "He Can't Love U" (released September 28, 1999) had similar success, reaching number 3 on the R&B charts and number 15 on the Hot 100. It also featured the track "Promise", which reached number 1 on the R&B charts and number 9 on the Hot 100.

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