Review: Tootsie World Premiere at Cadillac Theatre–A New Twist or an Old Drag?

A new comedy musical named Tootsie opened in a world premiere on Sunday for a limited engagement through October 14 before it heads off to Broadway in early spring. The Cadillac Palace Theatre was therefore packed with musical aficionados, producers and all of Chicago’s theater buffs craning their necks to see how this adaptation of the classic 1982 movie would hold up. Would it somehow be updated and re-invented to fit today’s social climate or stay true to the comic vision of an out-of-work actor getting fed-up and impersonating a matronly spitfire to gain a foothold in the acting world?

Tootsie opens with the ensemble belting out their anthem and quickly showing the hard knock life of the aspiring Broadway actor. Soon we get to meet Michael Dorsey (played by Santino Fontana). Fontana is the perfect person to embody both of his characters and to capture a hint of the Dustin Hoffman vibe. Fontana’s amazingly versatile vocal range gets a run for its money in this show, as he is called on to switch from singing baritone as Michael Dorsey to the crystal clear alto of Dorothy Michaels’ voice with rapidity and fluidity, and it is a marvel to watch him switch back and forth. Just as it is to watch Fontana’s quick costume changes from casual guy to drag queen.

Dorsey, considered difficult to work with, is let go from an acting job for voicing an opinion that is different from the directors. The plot of Tootsie is similar to the movie, but has had some tweaks and updates, largely based around the role Michael/Dorothy plays. His is cast in a Broadway play rather than in a soap opera, a difference that lends the musical an air of meta-dissonance, as the actual show often goes from portraying stage rehearsals, to auditions and to performances and back while we watch Michael switch between his two personas just as quickly and easily, as if he was born to do it.

Scott Ellis directs, with exultant music and lyrics by David Yazbek (The Band’s Visit). Musical direction by Andy Grody assures that the music remains the clear focal point of the show while director Ellis pieces all of the comic and scenic elements together seamlessly with flawless choreography (by Denis Jones) and acting. The resulting overall production values of the show, including sleek and realistic sets that magically float in and out with the actors, gives Tootsie a Broadway-worthy polish.

There are plenty of opportunities for the cast to steal the show, especially Lilli Cooper (who plays love interest and leading lady Julie Nichols with absolute aplomb and ease) and Sarah Stiles (who plays the neurotic ex Sandi Lester with perfect comedic timing and charm). Andy Grotelueschen (playing the best friend playwright Jeff Slater) brings in the most impressive supporting moves, and is the most believable character as the grungy and cynical intellect.

The plot nuances fall short because the adaptation often reaches for a good one liner at the expense of subtlety, with occasional forays in to uncomfortable jokes about female bodies and other gender-related differences. It’s unfortunate that the opportunity to play with gender roles wasn’t explored as well as the idea of gender presentation was explored. Sure, Fontana can rock the drag by zipping in and out of gowns and heels, but the question of who he is during these changes is rarely touched upon.

In fact, Tootsie’s central idea of the gender binary is still deeply rooted in the past. The act of Michael becoming Dorothy is an act he is ashamed of (albeit secretly intrigued by) and one that is greeted with horror or amusement by all who discover it, belying a transphobic attitude that is more aligned with the ’80s. More importantly, it is seen only as an opportunistic pursuit and never once considered a genuine expression of Michael’s identity. In Michael’s case, he is using gender as a way to get ahead, as if being a female affords someone more liberties, which smacks particularly ludicrous in today’s world. This is perhaps intended to be mitigated by the empowering feminist gestures he is making as Dorothy on behalf of women (by taking over the play he was cast as a supporting role in to become to lead character and essentially rewriting it). While Dorothy is wresting power away from the egotistical and predatory director (played en pointe by Reg Rogers as Ron Carlisle), she is also stealing the role away from her love interest, a problem that is glossed over in the name of her charisma. Every character in the show is inspired by this powerful feminist example, but we in the audience are meant to understand the real truth; it isn’t altruism or feminism or even a woman that is making these things happen. It’s a straight white cis guy who feels entitled to be a star and is willing to trample over a female friend’s trust (Julie) and take a female role from an actual woman (Sarah).

What a pity that the nuance was lost on the creators that with just one minor tweak to the character’s identity the play’s theme might have become a journey of self-discovery rather than just a farcical case of mistaken identity. Such a seismic shift would then read as commentary on the current social climate, an act that would not just push the envelope of the musical art from, but would also probably bring forth a tidal wave of support from the queer community and create an iconic smash hit. They had a golden opportunity to use an outmoded concept of cross-dressing as a comic ploy to bust open the notions of identity politics. By comically embracing gender play, and toying with the concept of the gender binary, Tootsie might have acknowledged the existence of transgender identity and thus elevated the conversation. And isn’t elevating the conversation, or even having the conversation, one of the true functions and goals of theater?

Imagine it! Virtually nothing in the play would have to be different, other than how Dorothy sees herself—and her journey to becoming Dorothy. She might have even kept her love interest, and everyone’s feelings of betrayal could have been set straight by an empowered woman belting out a tune about who she was and how they better get used to it. But I suppose a play like that is still a few years away from Broadway—and not quite in the vision of creators who are more interested in a safe bet. How fortunate for them then that what the plot lacks, the actors make up for in droves, using every gesture and facial expression to convey nuance, and that the music and snappy dialogue keep things rolling along and entertaining, putting Tootsie on track to be a hit nonetheless, just not a ground-breaking one.

It isn’t until the very end that a hint of gender transcendence is revealed when Julie admits to Michael that she misses Dorothy, and Michael says “You don’t have to. She’s right here.” And that is where the romantics and the queer among us can sync up and sigh at this bold show that implodes on the scene full of music, dance, drama, comedy and in the end, a bid for love and forgiveness.

Tickets for Tootsie are $35-$105. Tickets are available at all Broadway In Chicago box offices (24 W. Randolph St., 151 W. Randolph St., 18 W. Monroe St. and 175 E. Chestnut), the Broadway In Chicago ticket line at (800) 775-2000 and online.

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Kim Campbell

Kim Campbell (they/them) is a freelance editor, podcaster and creative writer who has spent a career focusing on the arts, particularly literature, theater and circus. Former editor of CircusTalk News, they have written about theater and circus for Third Coast Review since its very beginning. Kim is a member of the American Theatre Critics Association and the International Network of Circus Arts Magazines. In 2019, they were on the jury of FIRCO in Madrid (Circus Festival Iberoamericano) and in 2021 they were on the voting committee for the International Circus Awards. See their tweets at @kimzyn or follow them on Instagram.