Roy Proctor grew up in Thomasville, N.C., and graduated in 1962 from the University of Iowa, where he studied under Philip Roth in the Iowa Fiction Workshop. While at Iowa, he took the same playwriting course – same course number, different professor – that Tennessee Williams had taken 25 years before, but with a far different result. Proctor retired in 2004 after 30 years as the staff theatre and art critic on The Richmond (Va.) News Leader and, when that afternoon daily folded in 1992, the Richmond Times-Dispatch. In the next four years, he directed eleven plays for five Richmond theatre companies. He wrote The Hollow in September 2011, then completed twenty-one other short plays by the end of March 2012, eight of which he has combined into Madison Square, an evening of adaptations of O. Henry short stories set in Manhattan parks.