Comedian and Advocate Kaytlin Bailey Wants to Make the History of Sex Work “Willfully, Deliberately Accessible”

Kaytlin Bailey’s one-woman show, The Oldest Profession, is billed as “a mad dash through 10,000 years of history from a sex worker’s perspective.” Bailey’s experience as a sex worker and sex work advocate, and more recently as a podcaster and stand-up comic, has given her a well-rounded perspective on the history of “the oldest profession” and how best to share it. Her show, which began its life in 2019 under the title Whore’s Eye View, covers mostly Western history, from the Epic of Gilgamesh to the scientific revolution, and from medieval witch hunts to contemporary debates about the future of sex work. She also discusses her own career and the parallels between her experience as a sex worker and her father’s experience as a career US Army soldier.

I spoke with Bailey a few weeks before she brought The Oldest Profession to the Phoenix Theater in Minneapolis on July 17. By coincidence, it was the day that the Minneapolis City Council voted to repeal a nearly 40-year-old ban on adult bathhouses and sex venues, a move many consider a win for local queer and sex worker communities as well as a possible move toward decriminalizing sex work on a wider scale.

Kaytlin Bailey at the HERE Arts Center in New York City. Ashley Euckland

During our interview, I asked Bailey about her reasons for putting together a one-person show, as opposed to, say, a standard narrative play. She explained that besides it being significantly cheaper to tour compared to a production with a full cast, she wanted to harness the power of personal storytelling. “There is no barrier between you and the audience,” she said, adding that she wanted to create a physiological response in the viewer.

The Oldest Profession covers sex work history in a broad capacity, but it is indeed highly personal, and Bailey does not shy away from sharing her perspective and opinions on the history she brings up—through humor, since The Oldest Profession is primarily a comedy show, but also through more serious framing at times. For example, when discussing the Malleus Maleficarum, the infamous 15th-century witchfinder’s guide, she jokingly calls the book Bitches Be Witches, highlighting the misogynistic and overreactive nature of the text. On the other hand, discussion of how the forced celibacy of the Catholic priesthood has contributed to the systemic abuse of children is not a place to be funny.

Kaytlin Bailey at the Edinburgh Fringe Festival. Emily Oliver

In her more directly personal stories, Bailey spends a lot of time talking about her father, his military service, and how that affected his life and her upbringing. He grew up in poverty and joined the US Army at the age of 17 during the Vietnam War. He later became a Green Beret and was able to lift himself out of poverty through his military career. Bailey grew up comfortably and, as a result, was able to go to college and study history as opposed to a more “practical” subject.

Her father never really understood her career as a sex worker because, I gleaned, he never understood how his daughter could willingly and enthusiastically choose to do it. Culturally, sex work is conflated with exploitation, an issue that makes progress in that realm of labor rights hard to achieve. This aspect put a lot of strain on their once-close relationship in Bailey’s adulthood. She makes the point, though, that her father’s reasons for choosing to join the military were much the same as the reasons many women have for going into sex work: poverty and a lack of other options. During our interview, Bailey rhetorically asked what our culture might be like if we denigrated soldiers and celebrated sex workers.

Kaytlin Bailey at the PEN Theater in London. Jamie Mykaela

One of the biggest strengths of The Oldest Profession is its use of common, colloquial language (and, of course, comedy) to present the complex history and its associated issues. Bailey told me she wanted her show to be “willfully, deliberately accessible,” and something sex workers could bring their moms to see. I won’t get too into the details of precisely what history she covers, because then we’d be here all day, but there is heavy discussion of the areas where sex work and religion overlap, including in ancient Sumer, where it is believed that kings may have established legitimacy by having intercourse with priestesses of the fertility goddess Inanna (later called Ishtar). In medieval Europe, the Catholic Church itself profited from brothels, where Bailey says it at times sent women who were “caught” having had sex before marriage—sometimes via a ritual that measured the ratio of the head to the neck—if they couldn’t join a convent.

Bailey presents a wonderful slideshow as part of her set, including historical artwork, photographs, and text to aid her comedy and lend a much-needed visual dynamic to the show. For me, the highlight of this was a piece of 14th-century manuscript marginalia depicting nuns picking penises off of a tree. I audibly cheered when the image came up, since I was already familiar with the artwork from a medieval literature class I’d taken in college. It’s a fun little historical oddity, and it was a happy surprise to see it included.

Nuns pick penises from a tree in this margin artwork from a 14th-century French manuscript. History Collection

At the Phoenix Theater show, Bailey’s show wasn’t the only entertainment of the evening. Local drag artist and comic Miss Diagnosis opened the evening with a short set, and Bailey and members of the Minneapolis sex work advocacy community, including the owner of the Smitten Kitten and representatives from the Sex Workers Outreach Project, stayed after the show for a panel. These were both great additions. The panel in particular brought relevant local voices into the conversation, which helped me better understand the needs and desires of Minneapolis sex workers and what I could do as someone wishing to learn more about contemporary sex work activism. (You can learn about Minneapolis-based sex work advocacy on the SWOP Minneapolis website.)

Kaytlin Bailey was a lot of fun to talk to, and her show, while only a little over an hour long on its own, created a full evening of learning, fun, and interesting conversation. I for one hope she decides to come back to Minneapolis. You can find more information about her nonprofit organization, Old Pros, at OldProsOnline.org and more about The Oldest Profession and its upcoming performances at TheOldestProfession.org.