Alright – so today we’ve got the honor of introducing you to Denise Winkelman. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Denise, thanks for joining us today. Do you feel you or your work has ever been misunderstood or mischaracterized? If so, tell us the story and how/why it happened and if there are any interesting learnings or insights you took from the experience?

Absolutely. I’ve often been labeled as a queer comedian, which, while technically true, doesn’t fully capture who I am or what I bring to the stage. I often get booked on queer or diversity showcases and I love connecting with other members of my community. I’ve found that people sometimes assume my material only speaks to a niche audience. The truth is, my comedy reaches far beyond my identity.

I grew up in a conservative small town in Minnesota. I come from a religious family and spent over 15 years working in business. I was also a professional wrestler before transitioning, and a fitness model after. My life has spanned so many worlds — blue-collar, corporate life, locker rooms, and everything in between. My comedy blends all of that: stories about my past, my identity, and universal moments that anyone can relate to, whether or not they’ve ever set foot in a Pride parade, love wrestling, or just struggle with dating.

The biggest insight I’ve learned is that the more authentically I show up, the more I connect with all kinds of people. I’m not just a trans comic or a diversity booking. I’m a storyteller, a former athlete, a recovering Midwesterner, and a complete hussy. Comedy is about connection, and I’ve found that when I lead with honesty and heart, audiences see themselves in my story, even if we couldn’t seem more different.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m a comedian, writer, and former professional wrestler. I grew up in a conservative small town in Minnesota in a religious family, spent over 15 years working in business, and transitioned later in life after years in male-dominated spaces like athletics, wrestling, and corporate leadership. Comedy wasn’t something I planned. It was something I found when life cracked open. I started telling jokes as a way to have an creative outlet.

I’ve been through a lot: in wrestling, I performed everywhere from small-town gyms to dirt-floored county fairs, and in comedy, I’ve done bar shows with broken mics and big time clubs with sold-out crowds. It’s been a long road, but I relate to the spirit of Ashley McBride’s song “Girl Going Nowhere.” People underestimated me. They didn’t see the hustle, the pain, the transformation, or the punchlines. But I kept showing up. And I’ve built something I’m really proud of.

Today, I bring high-impact, high-energy storytelling to the stage. My debut comedy special Bougie on a Budget is coming out soon through Comedy Dynamics, and it weaves together stories about gender, identity, ambition, family, dating, and the absurdity of being human. It’s funny, raw, with a ton of heart- which is kind of me in a nutshell.

What sets me apart is that I’ve lived a dozen lives and can connect with anyone. I’ve been blue-collar, corporate, queer, closeted, center stage, and I use that experience to find common ground with every audience. I’m not here to preach. I’m here to make you laugh, maybe cry a little, and remind you that being yourself is a kind of superpower.

Whether you’re a comedy fan, a booker, or someone just trying to get through the day, I hope my work makes you feel seen, heard, and a little less alone.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

One of the biggest lessons I had to unlearn was the belief that being different made me a bad person or someone who didn’t deserve love, success, or belonging. I spent so much of my life afraid to let people get close, constantly worried they’d judge me or reject me if they really knew who I was. That fear kept me distant, even when I was outwardly successful or surrounded by people. I was always performing some version of myself I thought was “acceptable.”

But over time, I started letting go of that fear. I shared more of my story on stage, and instead of judgment, I was met with laughter, connection, and real support. I’ve been embraced in ways I never expected by audiences, by fellow comics, by complete strangers who say, “Thank you, I’ve felt that too.”

Now, I’m far more confident and I’ve learned that the parts of me I once tried to hide are actually the ones that resonate most. Being different doesn’t make you broken. It makes you human.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

Tons. I’m a huge fan of inspirational quotes, stories, and speeches — I find so much fuel in hearing how others lead, grow, and connect. Some of my biggest influences range from Kobe Bryant’s mindset to PJ Fleck’s “Row the Boat” philosophy, Oprah’s wisdom, and locker room speeches from coaches like Kevin O’Connell. I love people who build something bigger than themselves-people who lead with passion, challenge expectations, and inspire others to do the same.

Comedy-wise, I’m constantly learning from artists like Bert Kreischer, Tom Segura, and Roy Wood Jr., especially when they talk about the business side of the industry. Their openness about strategy and growth has helped me shape my own path. Wrestling podcasts also continue to play a huge role. That world taught me everything about performance, reinvention, and reading a crowd.

But maybe the biggest shift for me came from watching the George Carlin documentary. It truly changed my life. He reinvented himself four or five times -and not just a little. He was a different kind of comedian in the ’60s, ’70s, ’80s, and ’90s. He evolved with the times and stayed ahead of the curve. That blew my mind. He wasn’t just chasing relevance…he was growing.

For me, that’s the key: I want to keep evolving as a performer, as a writer, and as a human. I’m drawn to coaches because they lead people to do things that don’t come naturally, and help them to reach to their full potential. That’s the kind of energy I want around me: people who push limits, challenge comfort zones, and lead with heart. If someone’s passionate and creative I’m always listening

Contact Info:

• Website: https://www.denisewinkelmancomedy.com
• Instagram: @denisewinkelmancomedy
• Facebook: https://facebook.com/denisewinkelmancomedy
• Twitter: @dwinkscomedy
• Youtube: @denisewinkelmancomedy
• Other: Tik Tok @denisewinkelmancomedy

Image Credits

Mistress K…..El Portal theater