Chapman hails from the Queensbridge Housing Projects in Queens, New York City,[2] and helped spawn other hip hop artists such as Mobb Deep, Capone-N-Noreaga, Nas.

[citation needed] He is documented to be the first to use the phrase "illmatic" in 1988 on a record called "The Rebel", from the Marley Marl album In Control, Volume 1, which was an inspiration and influence on fellow New York rapper Nas.

[9] In 1988, he appeared alongside fellow Juice Crew members on the Marley Marl compilation album In Control Vol.1, on the solo tracks "The Rebel" and "Live Motivator".

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".

Over the years, Khadafi has appeared on songs with Raekwon, Kool G Rap, Big Daddy Kane, Planet Asia, Ghostface Killah, Styles P, A.G., Cormega, Sticky Fingaz, Pete Rock, KRS-ONE, Cappadonna, R.A. the Rugged Man, Jadakiss, Black Thought, Mic Geronimo, Sheek Louch, Ja Rule, Nature, Ali Vegas, Wise Intelligent, Blaq Poet, Chuck D, Reef the Lost Cauze, Canibus, Vinnie Paz, Apathy, Celph Titled, and the late DMX, among others.

In 2013, Canadian producer Marco Polo, known for his extensive work with Pharoahe Monch and Masta Ace, invited Khadafi to appear on “Astonishing”, a posse cut that also featured Large Professor, O.C., and Inspectah Deck.

Further, WiseRap, Zicc, DJ Midnite, and E-Ratic Beats, who are all British hip hop artists, featured him on their collaborative song “In Too Deep (London 2 Queens)” in 2021.

Then, in July 2022, he appeared with Guilty Simpson, Thirstin Howl III, Bonshah, Fraction, and Ultra Magnus on “We Gon’ Stomp Shit”, a posse cut by a Bahá’í rapper from Toronto named The Mighty Rhino.