Robert Brown was born on February 5, 1969, in the hardscrabble Orchard Park projects in the Roxbury neighborhood of Boston, Massachusetts. Brown had dreamed of becoming a singer ever since he saw James Brown perform at the age of 3. He started out singing in church choir, where he distinguished himself with his beautiful and passionate voice. At the age of 12, he formed a group with his friends Ricky Bell, Michael Bivins, Ralph Tresvant and Ronnie DeVoe. Calling themselves New Edition, they rehearsed with a focus and discipline very rare for a group of pre-teen boys. After winning several talent shows, New Edition was discovered by producer and talent scout Maurice Starr, who landed them a recording contract with a small label called Streetwise in 1983. That year they released their debut album, Candy Girl, a sugary sweet collection of songs that made the group an overnight sensation. The title track, "Candy Girl," was highly reminiscent of The Jackson 5's "ABC."

In 1984, New Edition switched to MCA Records and released a self-titled follow-up album that eclipsed the success of Candy Girl with hit singles such as "Cool It Now" and "Mr. Telephone Man." Believing that they were being treated "like little slaves by people who were only interested in money and power, and not the welfare of New Edition," Brown left the group in 1986 to pursue a solo career.

In December 1986, Brown released his first solo album, King of Stage. While the album sold modestly and scored one major hit with the ballad "Girlfriend," it failed to generate the level of excitement and acclaim for which Brown had hoped. Seeking to reinvent himself as an adult artist, Brown spent the next two years working closely with the acclaimed R&B songwriters and producers Teddy Riley, L.A. Reid and Babyface. The result of their collaboration, released in the summer of 1988, was a radically new R&B album called Don't Be Cruel that took the music world by storm, selling seven million copies on the way to becoming the bestselling album of the year. Brown's high-powered, sexually charged music and live performances earned him comparisons to his childhood idol Michael Jackson. In 1990, Brown recorded "On Our Own," the smash-hit theme song for the movie Ghostbusters II, and in 1992 he released his third album, Bobby, featuring the singles "Humpin' Around" and "Good Enough."