After being spotted by a La Face record executive at a talent show in his hometown of Atlanta, it took no time for Usher Raymond's career to take off. The 14-year-old auditioned for La Face co-founder L.A. Reid, who signed the gospel choir boy to a recording contract. Raymond was introduced to the world simply as "Usher," and released his debut album of the same name in 1994, which featured co-executive producer Sean "Puffy" Combs. The first single, "Think of You," gained Usher notoriety and reached gold status. From that initial exposure, Usher was approached to do other projects. In 1995, he recorded a national holiday jingle for Coca-Cola. He also joined several top male R&B vocalists to form Black Men United for the single "You Will Know," featured on the Jason's Lyric soundtrack. He also teamed with teen singing sensation Monica for a duet remake of Latimore's "Let's Straighten It Out."

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.