In 2012, Wolf wrote the film Guest House starring Michael Gross, Heather Lind and Mark Gessner. The film is based around real events in Wolf's life, and premiered at the historic TCL Chinese Theater for the HollyShorts Film Festival. In 2014, Wolf's production company, Howling Wolf Productions, produced The Quitter, an indie drama about a former baseball player who attempts to rebuild his relationship with his daughter. In 2014, Wolf wrote, directed and co-starred in The Walk alongside Peter Riegert. The film was adapted from an anecdote written in Rabbi David Wolpe's book “Why Faith Matters."