Maddi has worked with music figures such as Rah Digga, C-Bo, Jodeci, Ginuwine, Bizzy Bone, Devante Swing, K-Ci & JoJo, Flo Rida, DJ Quik, Jamie Foxx and Outsidaz.
With music rap group Bizness Clique they had a hit on the local radio station in Akron Ohio .
In 1998 Maddi wrote the majority of the soundtrack to the HBO documentary, Pimps Up, Ho's Down, directed by Brent Owens.
[6] In 1999, Maddi Madd worked with Grown Man Records and released the EP titled A Million Wayz which sold over 100,000 copies.
[11] In 2016, he appeared in indie slasher film "Rhyme Slaya" where Maddi played the role of rapper and club owner, "Solomon", aka "King Solo.