Brown joined the church choir, where he recognized and developed his singing abilities.New Edition was founded by 9-year-old Brown and childhood friends Michael Bivins, Ricky Bell, Travis Pettus, and Corey Rackley who all knew each other growing up in the Orchard Park Projects in Boston.
With the help of Machat and MCA representative Louil Silas, Brown began working with some of the top R&B producers and songwriters of the time, including Babyface, Antonio "L. The producers helped to compose what became Brown's most successful solo album of his career, Don't Be Cruel.
Released in 1988, the album launched five top-ten hits on the Billboard Hot 100, including the number-one single, the self-penned "My Prerogative", which became, along with "Every Little Step" and the title track, signature hits for the performer.
Brown's first full lead vocal performance was on the New Edition ballad "Jealous Girl," which was a minor hit when it also charted in 1983.
The group became pop sensations with their self-titled second release.
After performing in several talent shows in the Boston area in 1982, they signed a deal with fellow Bostonian Arthur Baker's Streetwise Records, who released their debut album Candy Girl.