Denise Winkelman: Comedian/Trans Woman/Former Pro Wrestler/Chronic Pain Sufferer

Episode 224

25th August 2025

When she was growing up in conservative, evangelical rural Minnesota, she knew. When she was excelling at sports, giving and receiving body slams and folding chair hits as a pro wrestler, she knew. Even when she married a woman while still living as a man, Denise knew that she was female. Denise figured it was […]

Episode notes

When she was growing up in conservative, evangelical rural Minnesota, she knew. When she was excelling at sports, giving and receiving body slams and folding chair hits as a pro wrestler, she knew. Even when she married a woman while still living as a man, Denise knew that she was female. Denise figured it was either suicide or take action to live her truth and fully transition. With her debut special, Bougie on a Budget, now streaming on Apple TV Plus and Amazon Prime, Denise opens up her gender journey and the joys and challenges she faced along the way. She reveals that her standup career took off when she acknowledged her transgender status on stage. Denise also discusses her life with fibromyalgia, a chronic condition that causes not just constant body pain and migraines but also depression, anxiety, and other mental health issues.

(As mentioned on the show)

Wits Reunion Show at the Fitzgerald Theater

John Moe’s writing classes at the Loft Literary Center

Math Emergency Farewell Show at the Amsterdam Bar and Hall

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In this episode...

Guests

  • Denise Winkelman

About the show

Join host John Moe (The Hilarious World of Depression) for honest, relatable, and, yes, sometimes funny conversations about mental health. Hear from comedians, musicians, authors, actors, and other top names in entertainment and the arts about living with depression, anxiety, and many other common disorders. Find out what they’ve done to address it, what worked, and what didn’t. Depresh Mode with John Moe also features useful insights on mental health issues with experts in the field. It’s honest talk from people who have been there and know their stuff. No shame, no stigma, and maybe a few laughs.

Like this podcast? Then you’ll love John’s book, The Hilarious World of Depression.

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