“Like what even is a feminine side?” Fontana said recently, at a theater district bistro, as he pushed a pile of pear salad around his plate.
A Broadway veteran, Fontana, who turns 37 this week, is originating his first true male musical lead in “Tootsie,” which starts previews at the Marquis Theater on March 29. If you squint, it’s his first female lead, too. “He has created two very different characters who live in the same body,” Robert Horn, the show’s book writer said.
“Tootsie,” based on the 1982 Dustin Hoffman film, with music and lyrics by David Yazbek, tells the story of Michael Dorsey (Fontana), an underemployed actor and top-notch narcissist. Desperate for work, he grabs a wig and a dress, crashing a friend’s audition in female drag. (In the movie, it’s for a soap opera, here a misbegotten Broadway musical: “Juliet’s Curse.”) He lands the part. Michael Dorsey becomes Dorothy Michaels. Dorothy Michaels becomes a star. Fontana’s feminine side sings a lot of the Act One numbers.
Broadway loves men who dress, and occasionally sing, as women. Take, say, “La Cage Aux Folles” and “Kinky Boots,” as well as the developing productions of “Mrs. Doubtfire” and “To Wong Foo, Thanks for Everything, Julie Newmar,” which cast Fontana in an early reading.
But Fontana typically presents as a lyric tenor, not a contralto, and he has never worn women’s clothes before, except once, in the 8th grade, when he skirted up as a cheerleader for a school skit. “It killed,” he said.
The two times I met him, once in Chicago last fall and once in New York in late winter, he was dressed low-key bro-ishly in jeans and baseball caps. One cap was red, the other one, classier, a houndstooth tweed. Dorothy is a departure.
Has his wife, actress Jessica Fontana, endorsed all this waxing? Mostly. Jessica Fontana was, she admitted, briefly jealous of his legs. These days she’s more supportive. “Now I’m just really happy for him and how good he looks,” she said.
And speaking of support, how strange does it feel to spend eight shows a week in pantyhose?
“It’s not any weirder than anything else,” Santino Fontana had told me when we met for an iced coffee just before his final performance in Chicago. “It’s all weird. If you’re really doing your job, you’re never being yourself.” Still, he was looking forward to that last show. “Oh my God, I’m just so happy I don’t have to shave tomorrow,” he’d said. “And I don’t have to wear that corset.”
But what makes “Tootsie” weirder, aside from the corset, aside from the twinned roles, aside from barn-raising a multimillion-dollar show that lives or dies on laughter, is the moment in which it arrives. Broadway has been reckoning, slowly, imperfectly, with the idea that musical comedies need to offer female characters full interiority and that maybe abuse — physical, psychological, verbal — isn’t so forgivable or funny.
That “Tootsie” is another musical with an all-male creative team makes it essential that it does right by women, even women played by men. But doing right can’t in any way stifle its reckless, headstrong comedy. Which is all to say that Fontana has some big kitten heels to fill.
Fontana was born in Stockton, California, the younger child of a teacher and an agronomist. He grew up in a small town in Washington state, playing baseball and acting in school plays: Wilbur in “Charlotte’s Web,” Jesus in “Godspell.” At the University of Minnesota, he completed a classical training program and at 24 he returned to Minnesota, playing Hamlet at the Guthrie. The Star Tribune compared him to “whiny ‘Friends’ star David Schwimmer,” then fell for his antic style.
He broke into Broadway quickly, playing mostly secondary roles, like the brother in “Billy Elliot,” like the brother in “Brighton Beach Memoirs.” He did play the prince in “Rodgers and Hammerstein’s Cinderella,” opposite Laura Osnes, but he wouldn’t really count that as a lead. “I would say, like, ‘I love how much Laura has to do,'” he said. His voice work in “Frozen”? Another prince, another second man.
His characters are often cocky and almost always agonizingly vulnerable. His face — 3/4 heartthrob, 1/4 muppet — has a trampoline’s elasticity and he usually looks like he has just thought of a joke he might or he might not tell you.
At a morning rehearsal, just a few days before we had dinner in New York, he and the company were working a scene late in the second act when Michael finally removes his disguise, a gender reveal party that tanks. The scene begins in Michael’s dressing room — a chair, a table, a sofa, a prop wig lolling like a dozing red panda. The show’s director, Scott Ellis, asked Fontana to try some slightly different blocking for a song. Fontana obliged.
But as his friend, playwright Stephen Karam had told me, Fontana “is meticulous in understanding every inch of a role.” So before he sat, before he stood, before he mimed putting on earrings, he took a few breaths to decide how and why Michael might move just then. Each gesture had to be made precise, intentional, cogent.
“He’s intense in the best way,” said Ellis who had told the show’s producers he would only direct if Fontana could star.
The word “intense” came up a lot when colleagues discussed Fontana. Also: “Smart” and “passionate” and “focused.” Is someone so “focused” tough to work with? A lot of people will recognize Fontana from “Crazy Ex-Girlfriend,” a popular television comedy that he insisted on exiting, a possible red flag. (For the record: He says he left because he’d never intended to do an hourlong series, because his wife’s career is in New York, because he missed theater. TV can wait until he’s “tapped out,” he said. Skylar Astin now plays the role.)
But every colleague I spoke to described his playfulness, his generosity. “He’s never throwing you under the bus to get a laugh,” said Joanna Gleason, who starred opposite him in Karam’s “Sons of the Prophet.”
Still, the character of Michael, a perfectionist and a straight shooter, pursuing his art like some creepy stalker, came easily. (Is Michael Fontana minus any emotional intelligence? Basically.) Dorothy was a tougher nut. She couldn’t be a joke, she couldn’t be a caricature. Michael invents her on the fly, yes, but the audience should still feel a waft of estrogen whenever she walks on.
To make Dorothy so persuasive that his wife has asked to hang out with her at home (“I was like, ‘You’re nuts,'” Fontana said), he began with hair and makeup — looks matter! Months before rehearsals for the Chicago tryout began, he sent some early makeup tests to Ellis, who emailed back asking, “What sick world are you in?”
He interviewed a bunch of women, his wife, his family, his friends, studying physical vocabulary. He borrowed especially from his mother. She doesn’t see the resemblance. He worked with Joan Lader, his longtime voice teacher, to find the right timbre for Dorothy.
“It’s not a cartoon voice,” Lader said, speaking by telephone. “It’s not like Mickey Mouse, it’s not really falsetto.” The notes, she said, “sound quite female.”
In Dorothy, Fontana found a character who has to walk the tightrope (yes, in heels) that many professional women will recognize. “She has to be,” he said, “assertive, but not bitchy, compassionate, but not emotional.” And unlike Michael, she still finds the energy to take care of everyone else in the room.
Fontana had more to do. He wanted a show that would be worthy of Dorothy, of the women who inspired her. He advocated for an ending in which Michael owns up to the women he’d defrauded, something the movie doesn’t include, “which is shocking,” he said. And he arranged a meeting with writer Rebecca Traister, who happens to be a staunch “Tootsie” fan, to discuss the show’s gender dynamics. They had several conversations that Traister, speaking by telephone, described as complicated and nuanced.
The first talk was on the day of Fontana’s first chest-waxing. “I felt he was extremely attuned to experiences he might not have been attuned to before,” she said. “He was deeply committed to this being a feminist show and that he wanted to do everything in his power to make it one,” she said.
Fontana wasn’t quite so forthright with me. Maybe he didn’t want to mansplain. The only time he used the word feminist was in praise of Traister. Maybe he didn’t want to take up more space than an actor should. But he did say, more generally, that while it’s up to men to listen to women it’s also up to them to become part of the conversation. “I want to help,” he said.
Standing up for his character has made him more aware of how men treat men, how men treat women, how people compliment his wife’s looks before they mention her talent, how his co-stars might sometimes need an escort to the subway, “because it’s dangerous to walk! Down the street!” He added a few expletives.
As Jessica Fontana told me, “This experience has given him true empathy.” He has had to listen to people obsessing over his hair and clothes and figure — “Pretty girl,” “Not so pretty girl” — and he has had to obsess over them, too, while also arguing about what a woman can do and say and be.
After the Chicago run, Fontana overheard her husband speaking to the costume designer, William Ivey Long, about that awful corset. As an actress who has sometimes had to sacrifice comfort for aesthetics, she listened in. She heard him ask if they could lose the corset, if they could find something less snug. And then she heard him say, “But I don’t want to sacrifice the waistline in that red dress.”
Just what a woman — or a man passionately committed to playing one — would say.
This article originally appeared in The New York Times.