Carmen Rupe

Carmen Rupe

Author: Old Pros October 7, 2025 Duration: 1:00:46

Carmen Rupe was many things—drag queen, sex worker, business owner, activist, icon—and almost the mayor of Wellington. This week, Kaytlin Bailey tells the story of New Zealand's most beloved old pro, tracing her journey from hula dancer to trans pioneer. Carmen's life was one of glamour, resistance, and love. She built safer spaces, fought unjust laws, and carved a path for generations to follow.

Special thanks to everyone I met in New Zealand who told me about this amazing old pro! Thank you NZPC for sponsoring my trip there. Thank you to the Ngā Taonga Sound & Vision Archive for letting us use some of the audio clips in this episode.

The Oldest Profession Podcast is produced by Old Pros, a non-profit media organization that uses storytelling to advocate for sex worker rights. 

If you value our mission, please consider making a tax deductible donation. To learn more visit us at oldprosonline.org, which is also where you can get Old Pros t-shirts, sweatshirts, totes, stickers, and more. Of course, proceeds from our shop support our work at Old Pros.

We'd like to thank our Season 6 sponsors M e g a P e r s o n a l s, Assembly Four, Tryst, A Great Idea, and the New Moon Network.


History is often told through the lens of the powerful, but what about those who operated in the shadows? The Oldest Profession Podcast turns the spotlight on the figures who shaped culture from the margins. Hosted by Kaytlin Bailey-a stand-up comic, advocate, and self-described notorious old pro-this series digs into the lives of specific sex workers from the past, placing them firmly within the context of their era. You’ll hear about courtesans who influenced politics, brothel owners who built empires, and street-based workers who fought back against oppression, all while drawing clear lines to the modern movement for rights and dignity. It’s a blend of rigorous historical research and the kind of candid, often humorous perspective that only someone with Bailey’s unique background can provide. Created in partnership with the team at Old Pros, this podcast doesn't just recount anecdotes; it argues that understanding these "old pros" is essential to understanding our collective story. The tone is engaging and accessible, merging the depth of a history lesson with the relatable punch of comedy. For anyone curious about the untold chapters of social history, this show offers a compelling, humanizing, and surprisingly funny journey.
Author: Language: English Episodes: 100

The Oldest Profession Podcast
Podcast Episodes
Victoria Woodhull Part Three [not-audio_url] [/not-audio_url]

Duration: 31:07
In part three, host Kaytlin Bailey recounts the end of Woodhull's life, and notes her impact on the Suffrage Movement that has somehow (yet also intentionally) mostly been forgotten. Victoria Woodhull was a suffragette,…
Victoria Woodhull Part Two [not-audio_url] [/not-audio_url]

Duration: 36:33
In part two, host Kaytlin Bailey notes Woodhull's crucial involvement in the Women's Suffrage Movement, and recounts the events that ultimately lead to her trouble with law enforcement. Victoria Woodhull was a suffragett…
Victoria Woodhull Part One [not-audio_url] [/not-audio_url]

Duration: 47:09
Host Kaytlin Bailey talks about Victoria Woodhull's early life and what led to her becoming an old pro. Victoria Woodhull was a suffragette, stock broker, rumored sex worker, and first female candidate for the President…
Lou Graham [not-audio_url] [/not-audio_url]

Duration: 17:06
At a time where full service sex workers in Seattle euphemistically called themselves seamstresses, Madam Lou Graham was so rich that she served as an alternative to banks, giving loans to business propositions deemed to…
Cardi B [not-audio_url] [/not-audio_url]

Duration: 22:45
The most famous sex worker of today's music industry, Cardi B unabashedly flaunts and celebrates her past as a stripper in her songs, music videos, and social media.
Henri de Toulouse-Lautrec [not-audio_url] [/not-audio_url]

Duration: 19:31
Best known for is commercial paintings of the moulin rouge, French artist Henri de Toulouse-Lautrec was also a john who (literally) lived in brothels. As a tenant and client, Toulouse-Lautrec created compelling portraits…
Ching Shih [not-audio_url] [/not-audio_url]

Duration: 17:46
Ching Shih went from working as a full service sex worker on a floating brothel in Canton to becoming the one of the most successful pirate captains in the history of the world.
Marilyn Monroe [not-audio_url] [/not-audio_url]

Duration: 25:44
In 1949, Marilyn Monroe, struggling to make ends meet as an actress, got paid 50$ to pose nude for a calendar. She worked as a pinup and, some say, as a prostitute before becoming an internationally recognized sex symbol…
Tlazōlteōtl [not-audio_url] [/not-audio_url]

Duration: 19:40
This Mesoamerican Goddess was the deity of vice, filth, purification, steam baths, lust, fertility, adulterers and, you guessed it, sex workers. She symbolically castrated priests in elaborate rituals, and provoked and p…

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