Wolk's career started in the theater in New York City, New York, writing and directing plays that were shown at theaters such as the Lincoln Center Institute, LaMaMa, Ensemble Studio Theater, and the Manhattan Theater Club, the latter of which he was on staff for five years. Wolk also taught at Brooklyn College, the New School, Lincoln Center, and Robert Redford's Sundance Institute. In his film credits, he wrote and directed the acclaimed HBO made-for-TV movie Criminal Justice, which Time Magazine named one of the "Ten Best" films of the year. The film went on to receive the Silver Prize at FIPA in Cannes, was named Best Cable Movie by The Cable Guide, and was nominated for a Writer's Guild Award. Previously, Wolk received the Writers Guild Award for Natica Jackson, which starred Michelle