Born in Houston, Texas, Freeman went to the local High School for the Performing and Visual Arts before later graduating from the University of North Carolina School of the Arts in 1987.
Freeman has been an ensemble member of the Steppenwolf Theatre Company in Chicago, Illinois since 1993. In the same year, he was nominated for the Tony Award for Best Actor in a Play for his lead performance in the Apartheid drama The Song of Jacob Zulu. More recently, Freeman has played the role of Doctor Dillamond from Wicked in the first North American tour, Chicago and Broadway productions. In 2015, he was nominated for his second Tony Award, this time for Best Featured Actor in a Play as Sissy Na Na in Airline Highway. He won the Drama Desk Award for Outstanding Featured Actor in a Play for the same role.
He has also had supporting roles in various films such as Grosse Pointe Blank (1997), The Cider House Rules (1999), and The Dark Knight (2008). On television, he is perhaps best known for his recurring role on Buffy the Vampire Slayer as "Mr. Trick".
He portrays Mr. Poe in the 2017 Netflix series A Series of Unfortunate Events.
