First making a name for for himself during the ‘90s, but unable to generate any real success as a solo artist due to a variety of factors outside of his control, Skillz—formerly known as Mad Skillz—is more widely regarded in the present day for his contributions as a ghostwriter, in addition to his “Rap Up” series from 2002-2021 (excluding 2013) and ongoing Hip-Hop Confessions web series.

Born Donnie Shaquan Lewis in Detroit, Michigan on June 2, 1974, Skillz first grew up in Fayetteville, North Carolina for a short period before finally settling in Richmond, Virginia. After submitting a rap recording of himself for an ad he came across in an issue of The Source magazine, he received the honor to perform at the 1993 New York Seminar, where he came in second place against MC Supernatural in a freestyle competition. Despite this outcome, his “skills” were noticed by Atlantic Records, whom he signed with not long after.

His debut single “The Nod Factor” was released in 1995, followed by his debut album From Where??? on February 13, 1996. The album earned positive reception for its production and strong lyrics, but struggled commercially, not helped by the fact it was released on the same day as 2Pac’s All Eyez On Me and Fugees' The Score. Following his split from Atlantic Records and new friendship with fellow Virginia native Magoo, Skillz became affiliated with former members of the Swing Mob collective and a founding member of the VA Playaz Supafriendz collective, opening him up to appearances on Aaliyah’s “Are You That Somebody (Remix),” Timbaland’s Tim’s Bio: Life from da Bassment as well as Timbaland & Magoo’s Indecent Proposal.

Securing a deal with Rawkus Records near the turn of the century, Skillz released the three-track EP Ghost Writer / Together / 1, 2 Theory in 2000, with the first song revealing his extensive work as a ghostwriter up to that point. In 2002, his second album I Ain’t Mad No More was slated to come out, but due to the lackluster performance of its lead single “Crew Deep,” its release in the US was cancelled, with the album only receiving an official release in Canada on December 30th that year. After this, he decided to put out his subsequent albums independently.

Aside from his “Rap Up” and Hip-Hop Confessions series, Skillz has continued to extend his pen game as a ghostwriter for other artists, ventured into DJing, became the University of Richmond’s first artist-in-residence in 2018 and 2020 where he co-taught the course “Voice of Hip Hop in America,” and even earned a proclamation by Richmond’s Mayor declaring February 13th as Mad Skillz Day in 2019 to honor the twenty-third anniversary of his debut album and his positive influence on the city.