[2] Pickens started his professional acting career at the Roundabout Theatre in New York City playing Walter Lee in A Raisin in the Sun.

[2] In 1981, Pickens performed in the Negro Ensemble Company's production of A Soldier's Play, starring alongside Denzel Washington and Samuel L.

He went on to have recurring roles on The X-Files as Deputy Director Kersh, Curb Your Enthusiasm, The West Wing, Roseanne, Beverly Hills, 90210, JAG, and Six Feet Under.

He played alongside actors Ed Asner, Barbara Bain, Amy Brenneman, George Coe, and Wendie Malick.

The play was an open appeal and fundraiser for passage of U.S. House Resolution 808,[3] which sought to establish a Cabinet-level "Department of Peace" in the U.S. government, to be funded by a two-percent diversion of the Pentagon's annual budget.