Men Dressed to Win: The Dueling Damsels of the 2014 Tonys

The cast of 'Casa Valentina.' (© Henry Leutwyler)

The cast of ‘Casa Valentina.’ (© Henry Leutwyler)

Harvey Fierstein and William Shakespeare have a lot to answer for about the actors contending for this year’s Tony. In a field of 20, a half dozen are wearing dresses.

“I go through a lot of questions that would be asked about who these people are, because, frankly, I didn’t understand who they were till I did my research.” Mr. Fierstein said of the characters in his Casa Valentina—a cross-dressing club in the Catskills in the early 1960s. “The whole first act is asking questions and putting info out there, and then in Act Two, we find out it all has repercussions. The last thing I wanted was for the curtain to go up on a bunch of men in dresses and the audience laughs or walks out, so I really felt the pressure to make sure their humanity was at the forefront.”

Last year, Mr. Fierstein had another man in a dress up for Tony honors—Lola, the drag-club diva who sexed up the shoe business with Kinky Boots—and he expressed doubts about the character’s sexual preference. “I don’t see that character as gay—I see him as straight,” he said then. “He could end up a transvestite or a transsexual. I think he’s somebody just learning about himself—somebody who’s on a journey.”

Billy Porter played him gay and got the Tony for Best Actor in a Musical—ironically over Bertie Carvel, who was pretending to be a woman as well: Matilda’s Miss Trunchbull, a hard-nosed, pants-suited girls-school headmistress who curdled the crème de la crème. Curiously, gender wasn’t an issue with that performance. “I take it as a compliment when people can’t believe a man is playing that part,” Mr. Carvel said. “I never thought it especially funny that a man was playing a woman. That’s not the gag. If that’s the gag, if that’s what people find funny, then we’re kind of lost.”

This year, there’s more gender-blurring going in the Best Actor in a Musical category, and both examples are high-octane, adrenaline-rushing performances.

The loudest and most conspicuous is Neil Patrick Harris, a mass of Barbie blondeness that comes out of the rafters of the Belasco Theatre and goes into a rock star rant and strut the instant his gold stilettos hit the stage in Hedwig and the Angry Inch.

The times have tamed the shock value that was first felt 15 years ago when John Cameron Mitchell sashayed onto the stage of the Jane Street Theatre as his self-created Hedwig. “The idea of a guy who is really a transgendered woman was so hard core it was almost a freak show in its newness,” Mr. Harris noted. Since then, the public’s familiarity with transgender situations has helped them “get beyond the deer-in-the-headlights” phase and helped him “play the part and tell the story, without [ingratiating] myself so much to the audience.”

Case in point is his strongest competition in the category, Jefferson Mays. As the East German gay transvestite in I Am My Own Wife, he has been there, done that, got the Tony, plus he did 36 other characters. He considers his work in A Gentleman’s Guide to Love and Murder—playing eight English aristocrats—“a walk in the park.” Two of them are “brutal battle-axes”: Lady Hyacinth D’Ysquith, a missionary-suffragette who drags Africans out of their huts to show them the virtues of colonialism, and Lady Salome D’Ysquith Pumphrey, a bad actress who didn’t know Hedda Gabler’s gun was loaded.

“I think I’m in a particularly strong position in that most of the women in the D’Ysquith family are much more masculine than any of the men,” reasoned Mr. Mays. “They wear the metaphor of the pants in the family, if not the actual. I do enjoy the liberation of wearing a dress, but I can’t fully enjoy it simply because I’m underdressed with other costumes. I wear layer upon layer upon—I’m an onion!”

In the Shakespearean category, Samuel Barnett was the only one of the boys who bellied up to the Bard last fall at the Belasco for Richard III and Twelfth Night who played two female roles, and both got him into the Tony category for Best Actor.

“I think it would be a mistake for me to kind of be a woman,” he opined. “An audience isn’t stupid. They know we’re men in women’s clothing. I think they’ll go with you as long as you’re being true to … what the character is feeling and thinking.”

His “scene partner” (Richard III to his Queen Elizabeth and Countess Olivia to his Viola), Mark Rylance, is also nominated twice—as Best Actor for the former and Best Featured Actor for the latter—and it may well be that the best performance of a female will take home the Tony for Best Featured Actor. Three of the five nominees qualify.

Paul Chahidi glided around with extraordinary feminine conviction and grace in a role heretofore lost in the background—Maria, Viola’s scheming lady-in-waiting. He even admitted his heart sank when he was offered the part. “It wasn’t any of the main comic parts that you usually notice,” he said. “In rehearsal, I thought I had the most boring person in the room. I felt, ‘I’m just delivering plot,’ which is what she does quite a lot of, but I grew to love this character. It’s not a very fully written role on the page, but there are so many gaps that Shakespeare has left to fill.”

Of the seven brave and excellent name-brand actors who inhabit Casa Valentina, Reed Birney is the most fascinating to watch melt, with no apparent effort, into an elegant, intelligent, at times poisonous female. “I knew he was an accomplished and versatile actor, but who knew he had such great legs?” swooned Observer critic Rex Reed.

“I don’t think I realized how liberating it would be to be in a dress,” Mr. Birney said. “It was terrifying initially—completely terrifying—but we were all terrified together. Ultimately, it has become hugely freeing. I don’t quite know why. I don’t really understand what I’m doing in the play. When I’m onstage, I find myself behaving in ways I don’t recognize. I’m like, ‘What’s happening? Who is this person? Where’s this coming from?’ I don’t know. It’s kind of miraculous or magical. It’s what you want to have happen as an actor. Something takes over, and you can get out of your head.”