Almost everything about the 1982 film Tootsie feels dated now: a male actor pretends to be a woman to get a part, he succeeds, and hilarity ensues. It was certainly a bizarre choice then for Robert Horn and David Yazbek to adapt it into a musical, especially one that is updated to 2019. Unsurprisingly, the Tootsie musical has quite a few problems in its discussion of gender, but it hides them (to varying degrees of success) under lots of comedy, choreography, and costumes. Without a doubt, Tootsie is an old-fashioned musical — both in its content and its style — so it is not at all surprising that it’s getting a lot of love. The new musical, directed by Scott Ellis, opened April 23rd to mostly rave reviews and just this week it received 11 Tony Award nominations. But I just can’t bring myself to love it.

Just as the in the film, the musical tells the story of Michael, a white, straight, and cis actor who is entitled, arrogant, and difficult to work with. Seemingly unable to get cast in anything, he decides to dress as a woman, named Dorothy, for an audition and lands the role. Here there is a heavy dose of a metatheatricality added, since he is cast in a Broadway musical, albeit a horrible one entitled Juliet’s Curse, a sequel to Romeo and Juliet. Yazbeck’s songs for the purposefully terrible musical are a comedic delight, as is quite a bit of Horn’s hilarious book, but the style differences between the “bad” musical (Juliet’s Curse) and the “good” one (Tootsie) is often non-existent. Although the comedy of Tootsie is easy to enjoy, much of the music and lyrics feel unmemorable, recycled, and non-specific.

Design-wise, there is little to love here. David Rockwell’s set is flanked by a New York City skyline that looks straight from a regional theater stock warehouse. The three sets of costumes — the modern attire, the Renaissance garb of the show-within-a-show, and 1950s silhouettes for the retooled production retitled from Juliet’s Curse to Juliet’s Nurse — are fun, but seem all wrong — not to mention the fact they are designed by William Ivey Long, who despite an allegation of sexual assault (which Long has denied) is still managing to get work on Broadway and just received Tony nominations for Tootsie and Beetlejuice.

The problem with the book and with the content of the musical is another story, and it is here where most of the larger problems lay. The musical relies on the terribly dated “man in a dress” comedic trope, which is deeply rooted in transmisogyny. The almost entirely-male creative team doesn’t even come close to having any meaningful discussion of drag or of gender; everything being a means to an end, in this case, a laugh. They seem unwilling and unable to explore any of the nuances of gender — like what if Michael is a trans lesbian and Dorothy is more than just a persona to get a role? They not only don’t entertain that conversation, but even worse, they seem unaware they should discuss gender identity at all.

In an interview with Playbill, leading man Santino Fontana ironically said that this musical is “perfect for the moment” and is a great exploration of gender inequality. But Tootsie is dated and still relies on sexism, ableism, homophobia, and transphobia to get laughs. It is rife with jokes about genitalia — like a reference to Dorothy being “half-cocked” or “not the package you imagined” — and extended bits about Michael getting into and out of drag, like “I am a man in love! Toss me my bra!” These are supposed to be comedic, but they just come off an uninformed and transphobic.

But it’s the comedic style of the musical that makes responding to Tootsie so complicated; objectively hilarious, it is easy to get swept up, but sneakily mixed in among the hilarious lines about show business are the problematic quips that mock drag, gender expression, and queerness. The very notion of a man in a dress is always and only a joke for Tootsie, as is the sexuality of the female characters.

Lilli Cooper, who plays Julie, the star of Juliet’s Curse and Michael (and Dorothy’s) romantic interest, does an excellent job with a tragically underdeveloped role. Michael falls in love with her, manipulates her, temporarily makes her think she is a lesbian, and then despite massive betrayal, in the end it is implied that they end up together. Throughout, her sexuality is a joke. For example, when she is describing her ideal man, it is played for laughs and when she believes she is a lesbian, the very idea of queerness is considered comedic. Although the character has been updated from the original, it doesn’t go far enough. Similarly, though Sarah Stiles gives a hilarious performance as Sandy (Michael’s friend), her only role is to sing and reprise a patter song that jokes about her being neurotic and overly emotional.

In a painful, ironic twist, Michael (as Dorothy) has a preachy speech about women being labelled hysterical and dealing with sexism in the workplace; he even has a supposedly feminist rant that lends the musical its title: “My name is Dorothy. Not precious, or honey, or Tootsie.” This speech is very similar to the one in the film, and the fact that the musical has not added anything new speaks to the weakness of the "updated" adaptation. For the entirety of the musical, it is the men who are woke and have the most to say about sexism, primarily Michael, who believes “what Dorothy is doing is important,” but also his roommate Jeff, played by Andy Grotelueschen, and his agent, played by Michael McGrath. The musical goes out of its way to have the male characters be mouthpieces for feminism, as if these brief apologist monologues can make up for the rest of the show. God forbid the women actually be given a chance to speak about sexism.

Of course, the transphobic and misogynist premise, poorly written female characters, mocking of queerness, and faux-feminist male characters should not be shocking at all coming from all almost all-white male cisgender creative team. It is clear Yazbeck and Horn are desperately trying to re-brand Tootsie as modern and feminist, but it fails in almost every aspect. Their slight efforts of infusing wokeness come across as forced, misguided, misplaced, minimal-effort afterthoughts, too little too late. We all need to look beyond the sequins and jokes, see the deep problems hiding underneath, and accept that in 2019, Tootsie cannot be saved, and quite honestly, it shouldn’t be.

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