In 2011, Masterson guest starred as James Roland in USA Network's "White Collar" (episode "Where There's A Will"). He portrayed Jerry Rubin in the 2010 movie, "The Chicago 8", written and directed by Pinchas Perry. "The Chicago 8" is a film based on the actual Chicago Eight in the late 1960s and early 1970s, and explores the events associated with the trial. It was filmed in September and October 2009. The film is based closely on the trial transcripts and most of the action takes place in the courtroom.