Many an actor has played Shakespeare’s problematic Shylock, the centerpiece of Shakespeare’s Merchant of Venice, since Elizabethan times. Even in “officially” Jew-free England (nominally from 1290–1656, though Sephardic Jews fleeing the Spanish Inquisition did live there), stereotypes of Shylock the Jew prevailed. Yet relatively rarely has a Jewish actor been cast as Shylock, especially in today’s “cancel culture.” In Playing Shylock, dramatist Mark Leiren-Young’s solo play, actor Saul Rubinek channels this issue.