'Awards Chatter' Podcast — Santino Fontana ('Tootsie')

Santino Fontana attends the 85th Annual Drama League Awards - Getty-H 2019
Walter McBride/WireImage

"I've been working within these 10, 14 blocks since I moved here in 2006," the actor Santino Fontana says as we sit down at his publicists' Times Square office to record an episode of The Hollywood Reporter's 'Awards Chatter' podcast and begin talking about his best actor in a musical Tony nomination for the first-ever musical version of Tootsie. Fontana, who was previously nominated in the category in 2013 for Cinderella, continues, "It's lovely to be seen and to be recognized and to be part of a community of artists who I also admire and I am honored to be considered amongst. These last couple of weeks have been exciting and tiring and surprising and all of the above." But, he hastens to add, "I'm still in it. I've got work to do. It's not over."

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LISTEN: You can hear the entire interview below.

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Fontana was raised between Stockton, Cal., and Richland, Wash., dabbling in the performing arts wherever possible. But it was as a member of the inaugural class of a BFA program that brought together the University of Minnesota and Minneapolis' Guthrie Theater that he learned "the importance of what we're actually doing" as actors.

Throughout his school years, Fontana "tried to hide" that he could sing, fearing that he would be pigeonholed. He found work in plays — his first major professional job, at just 23, was playing the title role in a Guthrie production of Hamlet — but, soon thereafter, he moved to New York and began to embrace his musical gifts, as well, first appearing Off Broadway in The Fantasticks and then making his Broadway debut in a 2007 revival of Sunday in the Park With George.

Fontana began steadily making a name for himself in Broadway productions ranging from Billy Elliot, which won the best musical Tony, to Brighton Beach Memoirs, for which he won the best featured actor in a play Drama Desk Award in 2010. But a head injury that he sustained during a 2010 performance of A View From the Bridge resulted in a "a contusion on my brain the size of a baseball," which not only put his career on hold, but, for a period, threatened his life. "It was terrifying," he says.

A year later, though, Fontana bounced back, starring in an acclaimed Broadway production of The Importance of Being Earnest (he met his future wife, Jessica Hershberg, during the run), and then in Stephen Karam's Off Broadway production of Sons of the Prophet, which was later a finalist for the 2012 Pulitzer Prize for Drama. Meanwhile, 2013 was his year of princes — one on Broadway in Cinderella, for which he received his first Tony nom, and the other in Frozen, the Disney animated film that became an international phenomenon. And then, in 2014, came a plum part opposite Tony Shalhoub in Act One, which was nominated for a best play Tony.

Fontana found his largest audience yet on The CW show Crazy Ex-Girlfriend, playing Greg, the gruff bartender who becomes a love interest of Rachel Bloom's Rebecca. He stayed with the show for only one season, though, because it was not what he signed up for — he had originally been told it would be a 10-episode, half-hour Showtime half-hour, and instead it became a 22-episode hourlong cable show — plus he didn't want to be on the other side of the country from his wife at the outset of their marriage. While walking away from the TV show may have struck some as a poor career move, it actually made possible his greatest showcase yet.

Fontana already knew director Scott Ellis and composer David Yazbek — he actually participated in the first reading for Yazbek's The Band's Visit, which went on to win 2018's best musical Tony — before winning the leading role in Tootsie, the first musical version of the 1982 non-musical film comedy about a struggling actor who poses as an actress to try to get closer to the woman he loves. But he still had to go through a reading process to win the part, and remained attached to the project for its three years of development.

Now, playing both Michael Dorsey and Dorothy Michaels, Fontana has to dress, walk, talk and, most dauntingly, sing as believably as a woman as a man — something he proves he can do magnificently during the soaring number "I Won't Let You Down," which brings down the house at the Marquis Theatre eight times a week. The show, which originated in Chicago en route to opening on Broadway on April 23, has garnered rave reviews, sold more than $1 million in tickets at the box office each week and received 11 Tony nominations, including Fontana's.

The most famous line in Tootsie is, "I was a better man with you as a woman than I ever was with a woman as a man. I just have to learn to do it without a dress." Has being a woman in Tootsie made Fontana a better man? "Absolutely" he says, "but it's the same with any role, you know what I mean? If you're really paying attention and you're really being honest about trying to step into somebody else's shoes, you're going to learn more about yourself and humanity."