Skillz was born in Detroit, Michigan, but at a young age moved to Richmond, Virginia. He first made a name for himself by finishing in second place (Losing to MC Supernatural) in a national freestyle competition which resulted in a recording contract with Atlantic Records. At this time he went by the stage name Mad Skillz rather than just Skillz. Mad Skillz' Atlantic debut album, From Where???, and its single, "The Nod Factor", were released in 1996, but neither received much commercial or critical attention. The album's title was a reference to the regionalism in hip-hop, and at the time the state of Virginia did not have a large hip-hop scene. In the late-1990s more of a Virginia scene emerged, and he allied himself with fellow Virginia natives Missy Elliott, Timbaland, and The Neptunes. He made appearances on Timbaland's albums Tim's Bio in 1998, and Indecent Proposal in 2001; Timbaland made plans to sign Skillz to the Blackhand label he was developing; however, the label failed to materialize. He along with Danja Mowf, Lonnie B, and Kalonji, members of Skillz' Supafriendz collective, also appeared on a remix of Aaliyah's hit single "Are You That Somebody" in 1998.
More recently (2000) Skillz is known for his tell all single "Ghostwriter". Within this single, he names (but edits) artists for which he has written hit singles. It has alluding lines such as 'I'm a ghostwriter, I'm the cat that you don't see/I write hits for rappers you like and charge 'em a fee'. Un-edited versions of the track have not surfaced but Skillz is known to do a live performance in which he includes the names. In one live performance he mentions P. Diddy, Foxy Brown, Mase, Will Smith and Jermaine Dupri. One artist who openly admits Skillz has written hits for him is P. Diddy.
Skillz eventually got a deal with Rawkus, where he recorded his 2002 LP I Ain't Mad No More, the title of which commemorated the official change of his MC moniker from "Mad Skillz" to just "Skillz". The afore mentioned LP was never officially released in the U.S., however, during the Sprite Liquid Mix Tour in 2003 he sold some bootleg versions of this CD. The CD was re-packaged without several tracks as "Confessions Of A Ghostwriter" in 2005. A Supafriends LP, Supavision, and another solo LP. A client for the Mama's Boys management company which also includes Musiq, Skillz has been a featured artist at okayplayer.com, run by Questlove of The Roots. Since the year 2002 Skillz has done a year end "Rap-Up" song that encapsulates the events of the prior 12 months. These have been well-received among fans. Also, after the conclusion of the HBO series "The Wire," Skillz released "The Wire: 5 Seasons in 5 Minutes."
He is the creator of the web series "Hip Hop Confessions" a series of shows that gathers hip hop purists and hip hop lovers alike where they reveal something hip hop related that they have never told anyone. The show has featured Q-Tip , Peanut Butter Wolf, Kwame and Dj Jazzy Jeff. It can be viewed at www.hiphopconfessions.com
He has performed with The Roots, Mos Def, Talib Kweli, Common, Jay-Z, Will Smith, Dj Jazzy Jeff, DJ AM, among others. He is also the creator of The Rap Up a song that he releases at the end of every year that recaps the events of that year in song format.
Skillz's latest album was released Oct. 26, 2010 and is entitled " The World Needs More Skillz".