In the play, which closely follows Woolf's story about the eponymous young Elizabethan nobleman (played by Francesca Faridany) who changes gender but doesn't age over four centuries, Greenspan portrays Queen Elizabeth I and the Archduchess Harriett, who later turns out to be Archduke Harry, in drag. "I don't know that I approach a female character any different from a male character," says Greenspan. "It's more about the character and the style of the play."
As for his specific take on Elizabeth, who takes the young Orlando as her lover, he says: "My approach has been to find the infirmity of the aged queen and also her emotional strength. I have been working also on how tenderly she feels towards Orlando, and how hurt she is when she sees him with someone else."
Orlando hardly marks Greenspan's first time exploring his feminine side on stage. He starred in Cornbury: The Queen's Governor, William M. Hoffman and Anthony Holland's historical romp about the former New York governor with a penchant for wearing dresses, and he portrayed the evil mother in the acclaimed musical Coraline.
But clothes don't necessarily make the performer. In his own play, She Stoops to Comedy, Greenspan played an actress who performs in drag -- although he appeared on stage, looking like himself, dressed in male clothes. "I think it has more to do with the pretend aspect, to be able to take on a character regardless of age, regardless of gender, regardless of ethnicity," he notes.
Greenspan's busy acting schedule -- which has also recently included the Manhattan Theater Club revival of The Royal Family, a revival of his solo-work The Myopia which he paired with Plays, his adaptation of a lecture by Gertrude Stein; Michi Barall's Rescue Me; and Adam Rapp's The Metal Children -- is essentially by design.
"I really like the modulation in how much I have to do and what I have to do," he says. "Whether it's a principal role, a supporting part, or a small role, I'm open 24 hours a day, 12 months a year. I'll take what anybody offers. It's wonderful to work so much -- It's like every actor's dream."
Fortunately, all his time on stage hasn't seemed to have gotten in the way of a writing career. "If I have a deadline, I make it," he says. Recently, he provided a libretto for Jump!, an adaptation of songs from Tosca by composer Nora York and director Joanne Akalaitis; completed a new 45-minute monologue titled Jonas, which he will perform for the Transport Group in 2011; and written The Horses' Ass, an adaptation of an Italian Renaissance comedy by Pietro Aretino, about a homosexual who is being forced to get married that CSC will produce in a future season.
And then there is his romantic comedy Go Back to Where You Are, which debuts in Spring 2011 at Playwrights Horizons. "It has to do with a group of theater people, one of whom has been dead for 2000 years and has been sent back to earth to do something, " says Greenspan, who will play the part of the deceased character, an actor from Ancient Greece who in life had a very limited career. "He died bitter and has been festering in hell, where he keeps changing his shape because he never had much of an identity while he was alive. When he returns, he is granted the ability to change at will, but he gets involved with people in a way that he didn't anticipate."