Khadafi began his career as one half of the duo Super Kids, along with Queensbridge producer DJ Hot Day. This output caught the attention of Marley Marl, who in 1986 produced the duo's single "The Tragedy (Don't Do It)", and "Stunt of the Block". Chapman was then made a junior member of the Juice Crew, alongside artists such as Big Daddy Kane, Kool G Rap, and MC Shan. While in prison he became a Five Percenter and began working under the alias "Intelligent Hoodlum", and released the self-titled album Intelligent Hoodlum on A&M Records. The album was produced by Marley Marl (with co-production by Large Professor) and contained the singles "Back to Reality", "Black and Proud" and "Arrest the President".

This song marked the end of Chapman's overt focus on Conscious hip hop, Black history and political commentary in his verses. Working with Capone, Noreaga and Mobb Deep, recording "L.A L.A" a response to Tha Dogg Pound's "New York, New York", Intelligent Hoodlum then began working under the name Tragedy Khadafi in 1997 and created a group called "CNN" and ended up getting them signed to Penalty Records . He also executive produced the group Capone-N-Noreaga's debut album, The War Report.