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Again the La Face had their reservations about signing Usher because the album wasn't as successful as they anticipated. After graduating from high school, Usher continued to develop his skills as a stage performer and laid the groundwork for his second album.

At this time Jonetta Patton, Usher's mother took control of his career and put him in more talent shows the summer of 1995 building Usher a larger fan base and ultimately putting more confidence in L. He also appeared on their version of "Let's Straighten It Out", a 1995 duet with fellow Atlanta teen recording artist Monica; Usher developed a friendship with American record producer, Jermaine Dupri, with whom he co-wrote and produced several tracks for his second album, My Way, released on September 16, 1997.

Usher was going through puberty and having a difficult time adjusting his voice. Usher quickly adapted to the lavish lifestyle of Puff Daddy although in an interview with Rolling Stone, he expressed it as the "Hardest days" of his life.

LA Reid became skeptical of Usher and put his recording on hold thinking about dropping him from the label. "I had to knuckle up, figure shit out in New York" he said.

The EP, Versus, also produced the Hot 100 top-five single "DJ Got Us Fallin' in Love".

Looking 4 Myself (2012), also debuted atop the Billboard 200 chart and produced the Hot 100 top-ten single "Scream". Raymond and Looking 4 Myself received Grammy Awards for R&B singles "There Goes My Baby" and "Climax".

8701 (2001) produced the number-one singles "U Remind Me" and "U Got It Bad", and top-three single "U Don't Have to Call".

During this time period young Usher first met Chilli, his label mate who he would later date.

Preparing for his debut album, Usher lost his voice. From this point Reid didn't know what to do with Usher so he sent him to New York in the spring of 1994 to live with Puff Daddy to attend what Reid called "Flavor Camp".

There, his grandmother discovered his ability to sing, although it was not until Usher joined a singing group that she considered he could sing professionally.

In the belief that a bigger city would provide greater opportunities for showcasing his talent, Usher's family moved to Atlanta, Georgia, where there was a more conducive environment for beginning singers.

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