He is arguably most well known for his roles in The Wire and Prison Break. Wisdom was born in Washington, District of Columbia, to Jamaican parents. He is a graduate of Columbia University.
He appeared in four of the five seasons (primarily seasons three and four) of Home Box Office program The Wire as Howard "Bunny" Colvin.
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 a recurring roles in television series Supernatural, Happy Town, and Burn Notice. From 2012 to 2013, Wisdom was series regular in season one of American Broadcasting Company drama series Nashville, as Coleman Carlisle.