AAbout the Author: Mason Pilevsky

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Definitively Dylan

The Least Problematic Woman in the World – 05 October 2025

The Least Problematic Woman in the World diabolically uses one show to speak two very different messages to two very different audiences existing simultaneously in the Lucille Lortel Theatre: the transgender and the cisgender. For the cisgender audience member, I’d imagine that this show seems, well, a little much. But for someone who is transgender like me, the show felt like exactly enough. Dylan Mulvaney‘s solo show highlights the ridiculous journey of her transition through hyperbolic culture references that resonate most strongly with those who have gone through our own transitions and are all too familiar with the ridiculous demands life puts on us along the way. As a transgender man (as opposed to a transgender woman like Dylan), I very much related to wanting to be the least controversial trans person – taken seriously for who I am and nothing more. Yet when Dylan‘s journey took a liberating, absurd turn, I was comfortably able to celebrate the places where our journeys differ and thoroughly enjoy watching Dylan seize the lifestyle she desired. Along the way, I enjoyed original songs and hilarious bits that leaned into the campiness of queer culture while discussing issues that are life and death for the queer community.

Dylan started the journey of the show in heaven, when her angelic self was assigned by G-d to live on earth as a transgender woman, and then picked back up with her four-year-old self already being identified as a twink. This role was conferred upon her as a medical mitigation of her blossoming desire to wear women’s clothing, which proved to only be a temporary hold over. Before we know it, Dylan is holding a mock funeral for her gay male self as she boards the train to her new life as a woman. Disappointingly, from here on out her most scathing criticism comes from within the trans community, culminating in a (somehow also liberating) acknowledgment that some parts of one’s story are meant to be private. At the end of the show, a new Dylan stands before us, humbly clad, but equally and thoroughly blessed.

The camp performance style was very familiar to those in the audience who are queer: the videos (Caite Hevner) reminiscent of Randy Rainbow, the song on the treadmill reminiscent of Lady Gaga (and of course, Marilyn Monroe). The scenic design (Tom Rogers) evokes Barbie with all of its pink glory (and of course, actual Barbies). Lighting (Cha See) subtly suggested pride flags, and played a big part in helping Dylan with the show’s emotional shifts, making her isolation quite palpable at times. Costuming (Enver Chakartash) was an interesting element in that it worked in the reverse direction of the play. At the beginning, Dylan was costumed as an angel in her most elaborate look in the show. By the end, Dylan was at her most problematic, but her costume was at its least problematic – a subtle reminder of the non-binary nature of problems: being one thing means that there will always be people wanting you to be another.

Taken as a whole, the performance felt somewhat like what drag has become. Since the art was taken out of its place within the community and commercialized for public consumption, drag has become increasingly less about self expression and increasingly more about monetizing shock value. Dylan leaned into irreverence and shock value, but also had moments of barebones clarity; surprisingly these juxtapositions were well integrated and thoughtfully executed. In The Least Problematic Woman In the World, Dylan Mulvaney leans into all stereotypes in a thorough exploration of what it means to be a trans woman and how she makes sense of her experiences in a way that is healing and allows her to move forward. It was flashy, glitzy, glamorous, and irreverent— and it was also touching, raw, emotional, real, and utterly transformative.

I attended this performance on a press pass from Sunshine Sachs Morgan & Lylis.


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