Tobolowsky has appeared in over 200 films and television projects. He has worked in theatre, directing, and acting in plays in New York City, San Francisco, and Los Angeles. He directed one movie, "Two Idiots in Hollywood," based on his play of the same name.
He also co-wrote the film "True Stories" with David Byrne and Beth Henley. He was nominated for a Tony Award for Best Performance by a Featured Actor in a Play for the 2002 revival of "Mornings at Seven."