Chill Rob G’s first Hip Hop collaboration was being part of the original version of the Flavor Unit collective, which included Lakim Shabazz, DJ Mark the 45 King, and Queen Latifah, among others. He signed with Stu Fine’s Wild Pitch Records in 1987, and released one album, Ride the Rhythm, on the label. Ride the Rhythm’s tracks alternated between a somewhat hardcore sound and an easygoing, conversational tone. It was chosen by The Source as one of the 100 Greatest Rap Albums.

In 1989, the a cappella version of his song “Let the Words Flow” were sampled illegally and without permission by the German pop-dance crew Snap! in its hit record The Power. The song was a remix created by German producers Michael Münzing and Luca Anzilotti (under the pseudonyms Benito Benites and John “Virgo” Garrett III). After the song gained in popularity in Europe, and Arista/BMG records came calling (via Ariola/BMG, the group’s label in its home country), Münzing and Anzilotti recruited Durron Butler (aka Turbo B) to record a new version of the song, rather than continue lip-syncing the original Chill Rob G lyrics. It was this version that was ultimately used and promoted as Snap!’s official version.

Chill virtually disappeared from the Hip Hop scene for the next decade. He stated in an interview that it was primarily stress within his personal life (and hints at frustration with his label, Wild Pitch) that caused his recession into obscurity at the peak of his career.

He recorded a second album, Black Gold, on independent label Echo International. A deal with the record company was not reached and the album remained unreleased for years before appearing on iTunes on May 6, 2008.

In 1996, his track “Bad Dreams” was covered by British trip hop artist Tricky on his album Pre-Millennium Tension.

In 2002 he appeared on DSP’s album In the Red. He also recorded a song with R.A. the Rugged Man. He is currently[when?] recording with Skamadix, Dayta120 and the 45 King while working on several projects.

In 2015 Chill Rob G dropped an EP titled “Chilled, Not Frozen”.