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Tuesday, May 26, 2026

REVIEW: The OLDest PROfession Now Playing Theater WIT Through May 27, 2026

The Oldest Profession: Solo Comedy Show About Sex Worker History 
Three nights only at Theater Wit
May 25, 26 & 27

Running Time: 1 hour 30 minutes with no intermission 


GUEST REVIEW

By Barbara Belcore

I was so pleased to see The Oldest Profession at Theater Wit, with my daughter last night, and with only two nights left, I’d absolutely hurry to get a seat. Kaytlin Bailey delivers a fast paced one woman show that somehow manages to be hilarious, deeply informative, personal, and genuinely moving all at once.

Blending stand up, storytelling, and art history, Bailey traces 10,000 years of sex worker history while making the subject incredibly accessible, even for audience members who may know very little about it going in. The show balances humor with serious social commentary in a way that never feels preachy. I found myself laughing one minute and sitting with something profoundly uncomfortable or thought provoking the next.

One of the most powerful threads throughout the show was the comparison between Bailey’s experience as a sex worker and her father’s experience as a soldier, especially the irony that his profession was statistically far more dangerous. Her reflections on how society assigns morality and value to different kinds of labor were sharp and memorable.

The historical sections were fascinating too, from discussions of virginity tests and the weaponization of the word “whore” starting in childhood, to debunking myths like Mary Magdalene being a sex worker. Bailey also explores how institutions, particularly the church, shaped attitudes toward sexuality, women, queer people, and sex workers over centuries.

The opener, Lauren, was fantastic too and set the tone perfectly with a warm, funny set before Bailey took the stage.

It’s rare to see a show that is this funny, this smart, and this human all at the same time. I left entertained, challenged, and still thinking about it hours later.

Barbara is a Chicago-area home birth midwife, maker, theater enthusiast, avid reader, and mom of two quirky, creative teens. She is currently snuggling three cats who are perpetually convinced that they have never been fed.


The Oldest Profession is a solo comedy show by Kaytlin Bailey who is a comedian, former sex worker, and host of the acclaimed podcast of the same name. Bailey offers a new angle on the world’s oldest profession, reframing the story of western civilization in a fast-paced and profoundly moving solo show. The performance is enhanced by a projected art history slideshow.

Blending stand-up, storytelling, and lived experience with meticulously researched history, the show races through 10,000 years of sex worker history in a funny yet thought provoking hour. The performance makes use of a projected art history slideshow.

Check out The Oldest Profession HERE for more information and upcoming show dates: https://theoldestprofession.org/


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