Wisdom was born in Washington, D.C., to Jamaican parents. He is a graduate of Columbia University. He appeared in four of the five seasons (primarily seasons three and four) of the HBO program The Wire as Howard "Bunny" Colvin. Wisdom had initially auditioned for the role of Stringer Bell. He has also starred in the 2004 films Barbershop 2: Back in Business and Ray, and the 2007 film Freedom Writers. He landed a regular role on season 3 of Prison Break playing the role of a Panamanian drug kingpin named Lechero. He also had recurring roles in the television series Supernatural, Happy Town, and Burn Notice. Wisdom was once a Producer for NPR's All Things Considered.