Born in Chicago, Illinois, Skee-Lo was raised in Poughkeepsie, New York, then moved to Riverside, California when he was nine. He graduated from high school in Moreno Valley before moving to Los Angeles in 1990 and attending El Camino College. He converted to Islam around this time and joined the Nation of Islam. He first started rapping that year.
Skee-Lo's debut album I Wish was released in 1995, which he first started working on in 1993. The album was a huge success. One of the singles, "Top of the Stairs", was featured in the ending credits as well as the soundtrack to the 1995 film Money Train.
He quietly "retired" from rapping five months after the album's release because of a dispute with label Sunshine Records. Skee-Lo claims Sunshine Records took all the credit from the album's success, and he did not make a single cent from it. This was first revealed in a 2012 interview with L.A. Weekly, and he further said "So I refused to shoot any more videos, promote or record music. I'm not their slave. I wasn't working for free." After many years he eventually won the rights against the label in court.
Skee-Lo recorded a cover of the Schoolhouse Rock! song "The Tale of Mr. Morton", which taught sentence structure (subject, verb and predicate). The song appears on the 1996 compilation album, Schoolhouse Rock! Rocks.
In 1996, Skee-Lo became a VJ for both MTV's The Beach House and The Grind.
He also co-wrote "I'll Be Your Everything" by boy band Youngstown. The song is featured on the 1999 Inspector Gadget movie soundtrack.
In 2000 he returned to the music scene with a second album, I Can't Stop.
In 2011 he wrote "Burnin' Up" as part of the soundtrack of the 2013 horror movie
Killer Holiday from Lionsgate Entertainment. MTV produced a music video directed by Marty Thomas that was filmed at actor Howie Mandel's house, which was rented by his son to MTV without Mandel's knowledge. It was released under his own indie label, Skeelo Musik.
Skee-Lo made a guest appearance on a track called "Now You See My Life" with former Hollywood Undead rapper Deuce from Deuce's album Nine Lives in 2012.
Skee-Lo released his third album, Fresh Ideas, on his own label Skeelo Musik, via iTunes on November 13, 2012. It appeared in stores July 9, 2013.