After graduating from high school, Usher released his sophomore album, My Way, in 1997. In an attempt to display his maturity and songwriting abilities, Usher co-wrote six of the nine songs and enlisted the help of producers Jermaine Dupri, Babyface, and, again, Combs. The album's first single, "You Make Me Wanna," re-established Usher as one of R&B's hottest artists, and also made him a crossover sensation; it topped the R&B charts for 11 weeks, hit number two pop, and eventually went double platinum. Both of the follow-up singles, "Nice & Slow" and "My Way," also went platinum; the former stayed at number one on the R&B charts for eight weeks and became his first number one pop single. In the meantime, Usher launched an acting career, appearing in the 1998 horror spoof The Faculty and the 1999 urban high-school drama Light It Up.

To tide fans over, he issued a concert recording titled simply Live in 1999. Usher returned with his third proper album, All About U, toward the end of 2000. His third album, 8701 (2001), moved him from a teen pop star to a sultry R&B singer. In early 2004, Arista released the single "Yeah!" Produced by Lil Jon and guesting Ludacris, the addictive, lightly crunk cut fast became a club and radio favorite. By the time the Usher full-length Confessions dropped later that March, "Yeah!" had hit the top of the Billboard charts. The album itself was Usher's most mature work to date and won the Grammy for Best Contemporary R&B Album in 2004 while "Yeah!" took home the best rapped/sung collaboration award. ~ Lynda Lane, All Music Guide