Interview with Denise Winkelman

 

Denise Winkelman has built a life that seems almost too improbable to fit neatly into one biography. A girl who knew from an early age that something about the life expected of her did not fit, she grew up in rural northern Minnesota in a conservative evangelical environment, throwing herself into sports and eventually professional wrestling, while carrying a private understanding of herself that she could not yet fully express. That path eventually led her through transition, a new life in Los Angeles and, unexpectedly, comedy. Winkelman brings an unusually rich collection of experiences to the stage: former professional wrestler, writer, model and now stand-up comedian, with her debut special Bougie on a Budget turning stories about her Midwestern upbringing, gender journey, dating life and reinvention into something both hilarious and deeply personal.

 

There is a striking contrast at the heart of her comedy. She can talk about getting hit with folding chairs and body slams, then pivot into the vulnerability of finally allowing herself to live authentically. Her first time performing stand-up was an eight-minute set, and the response was enough to convince her that comedy was where she needed to be. She has since developed a style that combines storytelling, self-awareness, warmth and an instinct for finding the absurdity inside difficult experiences. As she has explained, the deeper message behind Bougie on a Budget is ultimately simple: be yourself. Her story also carries the texture of someone who has spent years performing different versions of herself, first because she felt she had to, later because performance became an art form. Today, Denise can turn that history into laughter without reducing its complexity. Her comedy is not simply about being transgender, or being a former wrestler, or growing up in Minnesota. It is about what happens when all those seemingly contradictory pieces of a person finally belong to the same life. And perhaps that is what makes her such an intriguing person to talk to: the journey from hiding to performing, from trying to fit a prescribed identity to creating a stage persona entirely on her own terms, and from surviving her past to finding material in it.

 

Monika: Denise, it’s such a pleasure to have you with me. Thank you for taking the time to share your story. There is a saying that the happiest comedians on stage are sometimes the saddest people in real life. Does that idea resonate with you?

Denise: Thanks for having me. It’s a really good question. Comedians are human. We all come from different backgrounds, have different struggles, and different reasons why we love making people laugh. You could work in a corporate office and have a friend that you talk to every day who seems incredibly happy and full of life and have no idea what kind of trauma they’re struggling with behind closed doors.

Because of podcasts, audiences have so much more access to who we are as people than they used to. The more time you spend around someone and the better you get to know them, the harder it becomes to hide who you are or what you’re going through. There’s something really powerful about being vulnerable and letting people see the real you, but we can do that in pieces. Being authentic doesn’t mean we have to share every detail of our lives.

The last ten years have had some incredible highs and some really difficult periods for me. I try to be real about the things I’m going through, but I also try to focus on the things that bring me joy.

“I was always able to make people
laugh.”

Every person sitting in the audience is going through something. Maybe for that hour, laughing is exactly what they need. So I don’t see happiness onstage as a mask for sadness offstage. Both can exist at the same time. I may be struggling through a terrible breakup or devastated over the loss of a parent and still be completely happy in that moment because I’m doing something I love. 

Monika: Before comedy took over, you studied mass communication, worked at PBS, and spent years in finance. Looking back, what did those very different careers teach you about communication, people, and yourself?

Denise: All of those experiences gave me confidence and taught me how to connect with people. I worked with people from different backgrounds, religions, political beliefs, and perspectives. We might not agree on anything, but once you get past the emotions, it’s so much easier to find common ground. Understanding why someone believes something doesn’t mean you have to agree with them.

I was always able to make people laugh. Humor helped me connect with people, whether I was working in television, finance, or just talking with coworkers. Comedy is very similar. Art is subjective. Once you build that connection with an audience, there’s this collective agreement that we may be very different people, but in this moment, we’re going to have a good time together.

Monika: Your five years as a professional wrestler included some extraordinary characters and experiences. You have described the wrestling community as surprisingly close-knit, and you were particularly nervous about how your former wrestling friends would react when you came out. What did their response teach you about the people who had shared that chapter of your life?

Denise: It taught me not to make assumptions about how people are going to react. I spent years keeping people at arm’s length because I was afraid of what would happen if they really knew me. With wrestling, we saw each other four or five times a week. We trained together, traveled together, worked shows, went out, and became incredibly close, but there was still this huge part of myself I kept from them. When I came out, they surprised me. Many of the people I had been afraid of telling completely embraced me. I was treated like a sister. They were protective of me and told me how happy they were for me. Many of those friendships became stronger because I wasn’t hiding anymore.

I did lose some friends, but I learned to give people the opportunity to show me who they are instead of deciding for them how they’re going to react or feeling like I need to apologize for who I am. If someone matters to you, give them that chance and then respond to what they actually do. We can put ourselves through years of fear over conversations that haven’t even happened yet.

Monika: After transitioning, you tried returning to wrestling for several months before eventually moving toward fitness modeling and then comedy. Was letting go of wrestling emotionally harder than you expected, given how important it had been to your identity?

Denise: It was hard to let go because wrestling had been such a big part of my life, but I never saw it as my identity. It was something I loved doing. It gave me a creative outlet, a community, lifelong friendships, and a place where I could be silly, perform, and have fun.

It also taught me so much about how to grow as a performer, work like a professional, adapt, respond in the moment, and collaborate with other people. My favorite part was always doing promos. When I tried wrestling again in Denver, I worked with a writer who wanted my character to be strong and silent, and it took away the part I loved most.

I was really looking for the right creative fit. Stand-up gave me the freedom to control what I created and what I said without relying on someone else to create that opportunity for me. From the moment I stepped onstage for the first time, I knew this was what I had been searching for. Wrestling was something I loved doing. Being a comedian feels like who I am and what I was put on this earth to do. 

 

“Being a comedian feels like who I am
and what I was put on this earth to do.”

 

Monika: At one point, radio was the entertainment career you imagined for yourself. What was it about radio that attracted you, and do you think that early fascination with having a voice eventually found its way into stand-up?

Denise: I think I was searching for a creative outlet before I really understood what that meant for me. I wanted to be creative, but I wasn’t really seen as a creative person. I’ve always loved radio, and I loved the idea of someone like Howard Stern being able to sit behind a microphone and talk to people about anything. It’s probably why I love long-form podcasts now.

I was incredibly quiet and soft-spoken growing up. I was very observant, and I could always make people laugh one-on-one, but I wasn’t someone who walked into a room and took it over. I went to a really small high school, and I remember making up these dumb one-liners and pickup lines just to make one of the girls in my class laugh. A friend overheard me one day and told me, “You need to do stand-up.” I was so uncomfortable speaking in front of a group that I thought there was no way I could ever do that.

Even in college, whenever I had to give a speech, people would rave about how good I was at public speaking. Wrestling gave me a way to perform with guardrails because I was playing a character and could get lost in it. It wasn’t until after I transitioned that I really became comfortable embracing that part of myself and owning a room. Now speaking in public is one of my favorite things on the planet to do. Looking back, radio and wrestling were different creative outlets that ultimately helped me find stand-up.

Monika: Your debut special, Bougie on a Budget, brings together your Minnesota upbringing, your life in Los Angeles, relationships, transition, and comedy. When did you realize that all these seemingly different chapters could become one story onstage?

Denise: I don’t know if there was one moment when I realized it. Those chapters all fit together because they’re all me. The special is me sharing this wild ride and all the different parts of my life that brought me here. What connects all of those stories is the theme underneath the special: Be You. Find out who you are, fight for that person, and never let them go. So much of my life was spent searching for who I was, and then learning how important it is to hold onto her once I finally found her.

Monika: Your first comedy performance was not at a tiny open mic, but an eight-minute set in front of roughly 300 people, despite never having performed stand-up before. What possessed you to say yes to such a daunting first opportunity?

Denise: I knew I was done with wrestling, but I was still looking for the right creative outlet. I basically made a checklist of what I wanted. I wanted to perform, write my own material, make people laugh, embrace being different, control my own voice, and not be forced into someone else’s box. I looked at that list and thought, that’s stand-up.

I mentioned that I was thinking about trying comedy to the president of a gender center in Denver, and he offered me eight minutes at their big annual fundraiser. I said yes and then worked really hard preparing for it. I was incredibly nervous, but it went well enough that when I walked offstage, I knew I had found what I was looking for.  

“Be You. Find out who you are, fight 
for that person, and never let them go.”

Monika: You moved to Los Angeles in 2020, just two weeks before the pandemic began. What was it like arriving in a city where you were trying to build an entirely new professional life, only to have the world suddenly shut down?

Denise: It was really hard. I had been in Los Angeles for two weeks, I was unemployed, and I knew maybe three people. Then the entire world shut down. I remember hearing a comedian tell a story about moving to Los Angeles right before 9/11. He stayed, made it through that period, and eventually looked back at it as this incredibly difficult thing he had survived. I kept telling myself the same thing. This is going to be hard, but I’m going to make it through. It ended up giving me an opportunity to completely focus on comedy. I met Dat Phan, and he invited me into the comedy community he was building on Zoom. I started doing his shows along with other Zoom shows, sometimes as many as five sets a day. I wrote constantly and did around 500 sets in 14 months. A lot of the material I developed during that time eventually became part of my special.

And the talent on those shows was legit. Dat, Claude Stuart, Sally Mullins, Anjelica Scannura, Joe Dalo, Bernice Ye, and so many other amazing comedians were doing them. I met hundreds of comics from Los Angeles, New York, Chicago, Toronto, and all over, and I’m still friends with many of them today. When everything opened back up, instead of coming back rusty, I felt like a much stronger comedian. I also suddenly knew people everywhere. Comics in Los Angeles would ask me, “How do you know everyone?” It was because for 14 months, we had all been sitting in little boxes on a computer screen doing comedy together. 

Monika: Is there a small everyday pleasure, ritual, guilty pleasure, or indulgence that reliably puts you in a better mood?

Denise: It changes all the time. Right now, putting on Flo Rida or Kesha will usually do it. If I need to laugh, I’ll listen to Sarah Tiana, Debra DiGiovanni, or Iliza Shlesinger, put on the Psych theme song or silly bits from the show, watch Aubrey Plaza clips from Parks and Recreation, or go down a rabbit hole of old Lyle the Intern clips from Letterman. If I need to feel inspired, I’ll watch the star-making stand-up moment in the final episode of The Marvelous Mrs. Maisel or listen to one of Gophers football coach P.J. Fleck’s best halftime speeches. Apparently my happiness routine is just very specific forms of silly chaos. 

Monika: Choosing a name is such a deeply personal decision, one that can hold layers of significance and meaning. How did you come to choose your name? Does it carry a special resonance for you, perhaps representing a part of your journey or embodying a particular feeling or aspiration?

Denise: Choosing a name is hard. It’s kind of like picking a tattoo. I wanted something unique, but not Prince symbol unique. The first time I saw the name Denise was in a Hardy Boys book when I was a kid. She was a love interest for one of the brothers. It was basically Hardy Boys: The College Years, just without Zack and Slater. We were northern hillbillies, so I had never heard the name before and had no idea how it was pronounced. The first time I finally heard someone say it, I thought, “That’s fucking beautiful. That’s it. That’s my name.” My middle name, Ana, has a more personal connection. My grandmother’s name was Anna. She was a huge influence on me growing up. She would let me dress as myself when I was with her, and she taught me how to bake, although I don’t remember how to do any of it now. Using her name as my middle name was my way of remembering her.

 

END OF PART 1

PART 2

 

All photos: courtesy of Denise Winkelman.

© 2026 - Monika Kowalska