The Oldest Profession at The PIT Loft Jan 4

Sun Jan 04 2026 at 08:30 pm to 09:30 pm UTC-05:00

The PIT | New York

Old Pros
Publisher/HostOld Pros
The Oldest Profession at The PIT Loft Jan 4

The Oldest Profession is a mad dash through 10,000 years of history from a sex worker’s perspective.


Kaytlin Bailey offers a new angle on the world’s oldest profession, reframing the story of western civilization. Weaving history, stand-up comedy, and lived experience in a fast-paced and profoundly moving hour-long solo show. The performance is punctuated by a projected art history slideshow.

The show opens with a comedic monologue introducing Kaytlin Bailey, her background as an Army brat, history major, and sex worker. She quickly transitions into the promise of the show, which is to cover 10,000 years of history from her perspective as a sex worker.


Alternating between her own family history, lived experience, and contemporary observations, we meet many canonized characters from history, and trace the evolution of the sacred whore from deified, to demonized, to diseased. We spend time in the ancient world revisiting the Epic of Gilgamesh, the story of Genesis, and meet historic figures including Phryne, Veronica Franco, and Victoria Woodhull. We learn the origins of the emergent sex worker rights movement, complicating figures like Gloria Steinem while lifting up Margo St. James and Carol Leigh.


Special interest is paid to the comparison between Kaytlin’s own experiences as a sex worker and her father’s experiences as a soldier. The vast history covered in The Oldest Profession is deeply informed by the relationship and divergent narratives between warriors and whores, which can be traced back to some of our oldest myths.


This show is for adults who want to laugh while they learn about a historically stigmatized community in a funny, approachable, and safe way. The show appeals to academics, comedy fans, history nerds, and sex workers alike, but also appeals to conservative dads, informed moms, libertarians, progressives, feminists, and folks in the LGBTQ+ community.


Event Venue

The PIT, 154 W 29th St, New York, NY 10001, United States

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