Chappelle and Brennan linked back up and created "Chappelle's Show." They wrote and produced virtually every sketch themselves. In the second season, Brennan was allowed to officially direct and helmed such sketches as "Charlie Murphy/Rick James," The Racial Draft," "Charlie Murphy/Prince" and the "John Mayer Sketch." Brennan received three Emmy nominations for "Chappelle's Show."
As of this writing, "Chappelle's Show" is the number one selling television show DVD of all time, selling nearly nine million units.
Most recently, he wrote with Seth Meyers at the White House Correspondents Dinner.