Some of Isaacs more recognized work includes: appearances in the television series Law & Order: Criminal Intent, and as Romeo in the Public Theater’s in the Park performance of Romeo and Juliet, and in the Public Theater's "Shakespeare in the Park" revival of Two Gentlemen of Verona. Isaac also played Prince John, later crowned King John of England, in the 2010 film Robin Hood.
W.E.is a romantic exploration of the mysterious connection across decades between two women confronting the consequences of desire. Caught in a loveless Manhattan marriage, abused and frustrated Wally (Abbie Cornish) obsesses over Wallis Simpson (Andrea Riseborough), the stylish American divorcee who captured the heart of Edward the VIII (James D’Arcy) who abdicated the throne as King of England. As the Duchess of Windsor, Wallis spends the rest of her life in the glare of celebrity exile. Inspired by the Duchess’ determination to pursue love in the face of social exile, Wally escapes into the arms of another man (Oscar Isaac) whose love sets her free. W.E. is Madonna’s second directorial film debut.