Robert Sylvester Kelly was raised in the Ida B. Wells Homes public housing project in Chicago's Bronzeville neighborhood by his singer mother, Joanne. Kelly's father was absent throughout his upbringing.
Kelly attended Kenwood Academy High School, where he was taught music by Lena McLin, whose uncle was black gospel legend Thomas A. Dorsey. She encouraged him to become a singer and has continued to remain an influence throughout his career. McLin also taught Chaka Khan, Da Brat and Jennifer Hudson.
Kelly formed the group MGM (Musically Gifted Men) with his friends Marc McWilliams, Vincent Walker, and Shawn Brooks. In 1989 they participated on the talent TV show Big Break, hosted by Natalie Cole, winning the $100,000 grand prize.
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