Are Men in Dresses and Wigs Still Funny in Comedy? – The New York Times

Fall Preview
As “Some Like It Hot” and “Ain’t No Mo’” head to Broadway, following runs of “Tootsie” and “Mrs. Doubtfire,” 10 artists reflect on an enduring trope and how it works, or doesn’t, today.
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Men in dresses are in vogue on Broadway. Just before the pandemic, there was “Tootsie,” and just after the shutdown, “Mrs. Doubtfire.” Now comes “Some Like It Hot,” a musical adaptation of the classic caper comedy about two men who dress as women to escape the mob.
The new season on Broadway will also feature an audacious play, “Ain’t No Mo’,” in which the main character is a flight attendant played by a man in drag. This year’s Tony-winning best musical, “A Strange Loop,” has scenes in which a goateed male actor dons a pink dress to portray the protagonist’s mother. And “Kinky Boots,” the once long-running Broadway show concerning drag-friendly footwear, has just returned to New York for a commercial Off Broadway run.
The history of onstage cross-dressing goes way, way, way back — think of the ancient Greeks and Shakespeare, Kabuki and panto, “Hairspray” and “Matilda.” A long line of performers — Milton Berle and Martin Lawrence, Dame Edna and Tyler Perry, Monty Python and “The Kids in the Hall” — have donned dresses in the pursuit of laughs. But now this longstanding theatrical device is considerably more contested.
In this spring’s Off Broadway comedy, “Which Way to the Stage,” two Broadway superfans had a blowout argument about whether drag is liberating (his view) or sexist (hers, at least when he dares to dress up as their idol, Idina Menzel). “Maybe it’s empowering for you to get up and do for a few hours a week,” the female character says of her friend’s drag act, “but for some of us it’s a [expletive] prison, and to be expected to look like that and be like that is exhausting and demoralizing.”
One can fit a number of genres and genders under a dress-wearing umbrella — there are men and male-presenting performers playing women, playing men playing women, wearing dresses for drama, wearing dresses for laughs, wearing dresses as a means of self-expression. And many artists see drag, performed by people of all genders, as its own distinct category of stylized performance.
Each new production prompts a new round of reflection, conversation, and occasionally controversy over whether these characterizations are sexist, transphobic, dated or delightful. The musical adaptation of “Some Like It Hot,” a 1959 movie starring Jack Lemmon, Tony Curtis and Marilyn Monroe, promises that the film’s plot and characters “have been updated for a modern audience,” and one of its lead actors is nonbinary.
One long-running production is now rethinking its practice. Since 1996, “Chicago” has featured a character, Mary Sunshine, played by a male soprano dressed as a woman, whose wig is dramatically removed to reinforce the line, “things are not always as they appear to be.” But the show has just posted a notice inviting performers of “any gender identity” to audition for the role; asked about the change, Barry Weissler, a lead producer, said: “Our collective understanding of gender and the art of drag has evolved over the past two decades. We updated our casting breakdown to reflect this.”
Discussion about the subject is evolving and fraught: Some of those we asked to reflect on the topic declined, including both book writers of “Some Like It Hot” (Matthew López, a Tony-winning playwright who previously wrote the drag comedy “The Legend of Georgia McBride,” and Amber Ruffin, the comedian and talk show host). But many agreed to share their thoughts, including one of the stars of “Some Like It Hot,” J. Harrison Ghee, the nonbinary performer reimagining the role of Jerry/Daphne played on film by Lemmon, and Jordan E. Cooper, who is not only the writer but also stars as the flight attendant Peaches in “Ain’t No Mo’.”
Among the others interviewed are two transgender performers: L Morgan Lee, who was nominated for a Tony Award for her featured role in “A Strange Loop,” and Angelica Ross, who is about to start an eight-week run starring as Roxie Hart in “Chicago,” and who voiced concerns about Mary Sunshine. Plus, a number of other performers and writers: the drag artists Charles Busch and John Epperson (Lypsinka); the actor John-Andrew Morrison, who wears the dress in “A Strange Loop” and picked up a Tony nomination for his performance; and three writer-performers who have considered these issues in their work, Harvey Fierstein (“Torch Song Trilogy,” “Kinky Boots”), Taylor Mac (“A 24-Decade History of Popular Music”) and Ana Nogueira (“Which Way to the Stage”).
Their comments, about the charm, the concerns and their own connections to the art form, are edited and excerpted.
J. HARRISON GHEE I was a child when I put on my first dress, but did it when no one was around! Growing up in a Black religious family in the South, it was very clear how folks felt about queerness in any form. After moving away, and getting time to find myself, the freedom and joy I found in my authenticity has been unmatched. I love to watch people try to process me, a 6-feet-4-inches Black nonbinary being, presenting in a spectrum of fashions.
JORDAN E. COOPER There’s the version of me that was 6, and doing plays in my living room — I would cut up my dad’s work uniform to make costumes. But the first time I was in drag-drag was for “Ain’t No Mo’.” I had no desire to play Peaches. But I ended up having to go on, and the role fit like a glove. It was wild. It was electric. It felt so natural, so organic, and I felt this sense of freedom in exploring my femininity.
HARVEY FIERSTEIN I don’t think I ever would have been able to get onstage with men’s clothing. When you put on drag, you are taking on the magical powers that you attribute to the other sex. I found it very useful in being strong.
TAYLOR MAC I used to feel like people would respond with more shock over me walking down the street wearing high-heeled shoes than over mass shootings in America. It’s been a strange thing to watch the rise of “RuPaul’s Drag Race” as something that is inspiring a lot more Americans to just calm down about men in dresses.
ANGELICA ROSS The joke is an old joke. It’s usually “Ha ha, look! A man in a dress! They’re not supposed to be in dresses!” And it sort of bucks up against our old ways of seeing gender and gender roles. It can be, and has been, extremely harmful because that then gives a cue for society sometimes to take trans people as a joke, especially if they aren’t, in society’s eyes, succeeding at presenting in a socially acceptable gendered way. So it’s a difficult thing. Like, your Martin Lawrence as Sheneneh? I loved Martin; I loved Sheneneh. Sheneneh was a real person to me.
CHARLES BUSCH A big source of the comedy trope was homosexual panic — what happens if a man is posing as a woman and another man is attracted to him? That’s comic horror, and it’s a staple. Today audiences are beyond that — even more conservative ones have progressed beyond that sort of humor.
FIERSTEIN Drag has been with every culture through the history of humanity. We have a very long tradition of it, from the time that women weren’t allowed to be in theater, to the kind that has some connection to sexuality. Broadway and drag have a long history together — it’s always been there. There’s nothing quite as theatrical. There’s nothing quite as sexy.
COOPER What makes it funny is not necessarily the fact that a man is in a dress — it’s because it’s making a mockery of the norm, of what people say we should be and how people say we should act. There’s a power in the defiance of what you say I should be and what you say I should look like.
JOHN EPPERSON What is it that pushes people’s buttons, whether in a positive or negative direction? To be honest, I don’t think of the dress that I wear as the important thing. To me the important thing is the presentation: Am I funny when I’m wanting to be funny? Am I thought-provoking when I want to be thought-provoking? The dress means nothing to me anymore.
JOHN-ANDREW MORRISON There is something about the ridiculousness of it that makes it an easy gag. Milton Berle used to do that — it was just Milton Berle in a dress, and it was an easy laugh. When [“A Strange Loop”] brought it up to me, I was absolutely terrified of it, because I didn’t want her to become a joke. Once I did put on the dress, my job then became to really ground her. I don’t think it’s drag, as much as I think it’s storytelling. I am playing a woman who loves her kid more than anything else in life, and I’m trying to be as believable as possible.
MAC I like it when men wear femme clothing and pretend to be women — I find that charming. They’re not performing women, they’re performing men performing women — it’s a totally different thing. Especially in that film, they’re in conversation with masculinity, and what it is.
GHEE I had never seen the movie prior to getting the audition. After watching it, I definitely had concerns about the tropes used and how those would be addressed in a modern context when we have much more knowledge and sensitivity around L.G.B.T.Q. issues. But after reading the draft of the script, I saw an opportunity for me to be pushed as an entertainer by playing Jerry and the opportunity to bring my own nonbinary identity onstage.
ANA NOGUEIRA Obviously we all love “Some Like It Hot” — no one is tearing down the film, and it feels like it was actually progressive in its own way, pushing the gender boundaries of the time. But now we’ve seen those stories so many times, that the joke, just for the joke’s sake, has gotten old. It’s no longer pushing boundaries — the boundaries have already been pushed. I don’t want to just dismiss it or get too angry about it when we’re all trying our best here to make good art. But if the punchline is simply that femininity is funny — that it’s silly, it’s unserious, and it’s always sexual — if the punchline is, “This is a man in a dress,” then I say let’s try to do better. I don’t think any story is off limits, but I do think every story and subject matter deserve scrutiny.
L MORGAN LEE I was invited to one of the open dress rehearsals for “Some Like It Hot” and remember sitting there thinking, “They are going to get celebrated for this, when what’s happening here is actually really irresponsible.” I remember leaving the theater feeling like they invited a few trans people to be in the space, but they didn’t ask our opinions. Even with “Doubtfire” and “Tootsie,” the big question just keeps coming up: Why do we need these stories today? I do have serious concern and question with how much our business seems to insist on using this trope, and my show [“A Strange Loop”] does not get a pass in any way.
MAC I think it can be used in a misogynistic way, but I don’t think it inherently is misogynistic. It’s not about making fun of women any more than we’re making fun of the world at large.
COOPER It’s making a mockery of the misogyny. You’ll never see a normal woman look like a drag queen. Because it’s a mockery of what is expected of women. It’s a mockery of the male-gazey big hair, stiletto high heels. Drag is femininity on 14,000 steroids.
LEE Drag is its own piece of art altogether. This person is not trying to make you believe they are the gender that they are playing in that moment. I don’t see Lola in “Kinky Boots” as the same as “Doubtfire” or “Tootsie.” It’s someone who is outwardly saying “I am a performer.”
FIERSTEIN Drag is an applied disguise. Drag is costume. Drag is makeup. Drag is wigs. Can you comment on the social roles of women, by doing drag? Yes. Can you be offensive doing that? Absolutely. Can you also be positive doing it? Absolutely.
NOGUEIRA Most of the time drag is fabulous, but it’s also a queer movement, and something happens when you try to bring those things to the mainstream: Are you having to oversimplify, when you put something on a Broadway stage, to appeal to the masses, and when you do that are you dumbing down some of the jokes and leaning on the punchline being toward women, toward trans women?
BUSCH With some really outrageous or clown drag, I could see why women would think they’re being portrayed as vulgar bitches, but I really don’t think that was ever the intention. I think what it is, is that traditionally men have been raised without a certain amount of color and flamboyance, and so for many young people going into drag, it’s a rebellion against the constraints of masculinity.
EPPERSON It depends on the individual perceptions. I have heard that two women left one of my performances in Los Angeles and were puking. But then I read an interview with Lily Tomlin who saw it as a feminist statement.
MAC Clothing is not gender. All clothing is drag. Drag is what you’re trying to communicate to an audience. If you’re saying “I am viewed as a masculine person, and I am wearing what is viewed as feminine clothing,” then that’s a particular story that you’re telling and it can be expressed for comedy or drama or anything in between. Sometimes I get comments like, “Haven’t we seen enough drag?” And my comment to that is, “Haven’t we seen enough suits?”
ROSS In “Chicago” there’s Mary Sunshine. I will not steer away from saying that the role of Mary Sunshine is definitely deeply problematic. I haven’t fully processed it, because I understand where it sits in the show, but it’s jarring for me — it actually makes me flinch. I clap, because his voice is beautiful. But it’s almost as if I am vicariously experiencing that moment, and thinking that today that could happen to me — that someone would want to try to disrobe me.
MORRISON When we were at Playwrights, I did have a wig, and the wig actually became a big bone of contention, more than the dress. There was a moment where I would take the wig off onstage, and there was something about the meta-theatricality of taking that off. So when we got to D.C. [at Woolly Mammoth Theater Company], I said if the wig is something that is going to cause a problem, then we don’t need it. People in the trans community were let down by it — something about the wig was a bridge too far.
LEE If you are constantly seeing this trope of men wearing dresses being viewed as funny, or being viewed as a commentary on things being ridiculous, it directly correlates to seeing people who are transfeminine, trans women, nonbinary, gender-expansive, or gender nonconforming and somehow finding it either funny or ridiculous that they are presenting or expressing themselves in this way, and that directly leads to violence. The simple act of some man putting on a dress is not really funny to us, because our lives are affected by this directly. I think this is a challenge that our show did not meet. The lens through which “A Strange Loop” is told is very raw, is very honest, is very authentic, but inside of that is also sometimes a lot of harm and dismissal of trans people, of women, and that’s the case in many gay lenses. As an actress inside of the thing, I can’t help but notice.
ROSS When you take an American classic like “Chicago” and you put a Black trans woman front and center in the lead, it not only makes room for people of color and my fans and audiences to see themselves and know that it’s possible for them too, if this is the direction that they want, but it’s also forcing some folks who are dragging their feet toward the line of equality for everyone.
GHEE I love when characters make me look at myself and really assess the fullness of who I am. The possibility of sharing that mirror with audiences and the potential to open their eyes by creating greater understanding really excites me.
COOPER Peaches is a statement, just as much as she is a good-ass time. She is a party, but she also, in her existence, is a statement: I can be whoever I want to be in my Blackness and in my queerness. My feet are going to hate her, and my skin might hate her with all that makeup, but I’m excited that more people will get to meet her.
NOGUEIRA I hope that going forward, we’re using gender consultants, we’re hiring trans women, we’re hiring drag queens, to tell those stories, rather than taking drag and cross-dressing from these more marginalized communities and using it. I think there is a feeling people have that that will take all the fun out of it, if we try to go through and make sure nobody is being offended. But that’s not what’s going to happen. It’s making sure the arguments are interesting and coming from a truthful place for the character. I’ll also say that I’m curious why there’s so little drag where women are dressing as men, where masculinity is being put on and maybe skewered. I would love for people to play with masculinity the way that they seem so excited to constantly play with femininity.
BUSCH Now we see Brad Pitt wearing a skirt on a red carpet, so the shock of that is long gone. If you’re going to do a man-dressed-as-a-woman story, you have to go a little deeper, a little edgier, a little more dangerous. You have to rethink it.
LEE I hope that there is more specificity in how creators choose to use this device. I’m not someone that wants to sterilize — you can tell your story any way you want to tell your story — I just want you to be mindful, and to be aware that you are not alone on this earth. There are other people who will be deeply impacted and affected by the work that we show, so in an effort to cause as little harm as possible, just be aware of what you’re doing.


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