Hamilton started singing in his church's choir at age 10. He attended South Mecklenburg High School where he sang in their award-winning choir under the direction of Mark Setzer. In 1992, he met producer Mark Sparks who encouraged Hamilton to leave Charlotte and head to New York City where he signed with Andre Harrell's Uptown Records. Hamilton co-wrote the 1999 hit "U Know What's Up" for singer Donell Jones. In 2000, he joined soul singer D'Angelo's international tour in promotion of the Voodoo album, on which he was a backup singer. On March 25, 2016, he released his ninth studio album What I'm Feelin' featuring guitarists Gary Clark, Jr. and Vince Gill with tracks produced by Mark Batson, Salaam Remi, and James Poyser. After one week, the project ranked number two on the Billboard R&B chart, representing his highest career debut. Hamilton works with the background singers the HamilTones, often performing soul renditions of hip hop tracks.