October 14

Gospel Roots

Usher Raymond IV is born to Usher Raymond III and Jonetta Patton. At 9, he begins singing in the choir at St. Elmo Missionary Baptist Church in Chattanooga, Tenn. Usher tells the Washington Post in 1998 that singing in the church was "like mental grooming in early ages...Like any other normal child, I had a lot of dreams."

A Bad Boy Debut

Usher, 15, moves to New York to work with up-and-coming producer Sean ''Diddy'' Combs, who has a makeover in mind for his protégé. Usher's self-titled debut album sells 500,000 copies, but is heavily criticized for its sexual content. "It was the wrong direction," Usher tells PEOPLE. "That whole bad-boy thing, me frowning for the camera – that wasn't me."

Brandy & Usher

Usher (pictured with costar Brandy) makes his acting debut with a recurring role on the singer-actress' hit UPN series Moesha. After playing Brandy's boyfriend, he nabs another role on the CBS soap The Bold and the Beautiful. "I've found a new love," Usher tells PEOPLE. "My acting is making me want to leave my singing."

December 25

Usher's Movie Debut

Usher makes his film debut in the Robert Rodriguez's sci-fi thriller The Faculty. "He has a natural style," Rodriguez tells PEOPLE. "I was impressed." The following year, he appears as a DJ (left) in the teen hit She's All That and stars with Rosario Dawson and Vanessa Williams in the hostage drama Light It Up.

August 07

Becoming a Grammy Winner

Usher, 22, releases his third album, 8701. "The album is really about my evolution as an artist, as a writer, as a producer and as a man," Usher tells USA Today. "I learned how music works dealing with Jermaine Dupri, and I learned how image works dealing with Puff Daddy." It sells 8 million copies with hits like "U Remind Me," "U Got It Bad," and "U Don't Have to Call." Usher wins two Grammys: Best Male R&B Vocal Performance for "U Remind Me" and the same award the following year for "U Don't Have to Call."

March 23

Usher's Confessions

Usher releases Confessions, which sells nearly 1.1 million copies in its first week before selling more than 15 million copies worldwide. On the strength of such hits as "Confessions," "Burn," and "Yeah!" Usher receives eight Grammy nominations, winning two awards for Best Contemporary R&B Album and Best Rap/Sung Collaboration for "Yeah!" "My feeling has always been that Confessions would be a landmark album for me," he tells Ebony. "I knew this album was going to be big. I couldn't wait for it to drop. I was like, 'I'm going to get ya'll this time.'"