He cut his first single in the late 1980s, “Watcha Gonna Do,” a song that was played locally on a hip-hop station.

He later connected with WC and the Maad Circle and contributed to their 1991 debut album, Ain’t a Damn Thang Changed.

By 1994, he had established himself in the Los Angeles rap scene and signed to Tommy Boy Records, where he released his debut studio album, It Takes a Thief.

Album single “Fantastic Voyage,” accompanied by a playful video, hit Number Three on the Billboard Hot 100.

[1972’s Music of My Mind.] I got that for my 12th birthday, that one and Fight the Power by the Isley Brothers. Songs in the Key of Life, my mother had that album at the house, so it was kind of weird that I didn’t know the song….

I went back inside my manager’s house to use the toilet before I rolled out, and that’s when I heard the track.

I walked into the studio, and asked Doug, ‘Wow, whose track is that?’ Doug said, ‘Oh, it’s something I’m working on.’ I said, ‘Well, it’s mine!’”.

‘As I walk through the valley of the shadow of death/I take a look at my life and I see there’s nothing left’ — I freestyled that; that came off the top of the dome and I wrote that down.

Tommy Boy reportedly did not think the song would fit for his next album and added it instead to the film’s soundtrack

Its success guaranteed its inclusion on his next album titled after the track, and it won a Grammy for Best Solo Rap Performance

(And while he never released “Rollin’ With My Homies” as a single, the song had an iconic placement in the 1995 film Clueless)

He was tapped to rap the theme song for the Nickelodeon comedy series Kenan & Kel, “Aw Here it Goes.” He also began pursuing acting and he made his on-screen debut in a cameo for 1996 comedy Phat Beach and had a part in 1997’s Batman and Robin

Coolio released My Soul in 1997, which featured the single “C U When U Get There.” While he ran into some legal trouble that derailed the success of that album — an arrest in Germany for alleged shoplifting and assaulting the shop owner and a charge for carrying a concealed weapon a year later in California — he continued to work in the acting realm, starring as triplets in the film Tyrone and was a regular on Hollywood Squares