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
Old Pro Panel: Jack the Ripper's Victims [not-audio_url] [/not-audio_url]

Duration: 54:33
To conclude our series on Jack the Ripper's victims, our Old Pro historian Dr. Charlene J. Fletcher hosts a panel discussion with Charlotte, a spokeswoman for the English Collective of Prostitutes (ECP) and AK Saini, a c…
Tina Horn [not-audio_url] [/not-audio_url]

Duration: 1:00:00
Recorded during the release of our series on Jack the Ripper's victims, Kaytlin and Dr. Fletcher had the great pleasure of speaking with Tina Horn. Tina is the creator and writer of the sci-fi sex-rebel comic book series…
Mary Jane: Jack the Ripper Victim [not-audio_url] [/not-audio_url]

Duration: 21:13
This is the final episode of our series on the women murdered by Jack the Ripper. Mary Jane Kelly, generally considered the fifth and final victim, was found dead on November 9, 1888. Stock Media provided by sounddogs /…
Kate: Jack the Ripper Victim [not-audio_url] [/not-audio_url]

Duration: 34:53
This is the fourth episode of our series on the women murdered by Jack the Ripper. Catherine Eddowes, also known as Kate (which is how we reference her) was found mutilated in the southernmost corner of Mitre Square on S…
Elisabeth: Jack the Ripper Victim [not-audio_url] [/not-audio_url]

Duration: 38:16
Continuing our series on the women murdered by Jack the Ripper, this episode focuses on his third known victim. Elisabeth, an immigrant from Sweden, was found murdered on September 30th, 1888. Stock Media provided by sou…
Annie: Jack the Ripper Victim [not-audio_url] [/not-audio_url]

Duration: 22:16
Continuing our series on the victims of Jack the Ripper, this episode is about Annie, who was brutally murdered in London's East End on September 8, 1888. Stock Media provided by sounddogs / Pond5
Polly: Jack the Ripper Victim [not-audio_url] [/not-audio_url]

Duration: 31:49
Late in the summer of 1888, a serial killer murdered at least five women in London's East End. The press at the time was quick to paint his victims as prostitutes, punished for their promiscuity. This series tells the fu…