TRANSCRIPT Depresh Mode Ep. 224: Denise Winkelman: Comedian/Trans Woman/Former Pro Wrestler/Chronic Pain Sufferer

[00:00:00]

John Moe: A note to our listeners: this episode contains mention of suicidal ideation.

Try to meet interesting people in this life. That’s my advice. Treasure your friends, spend time with your family—yes, yes, of course. But also, do what you can to meet people far outside your range of experience. Let them meet you, since you are far outside their range of experience. Get to know as much of the range of humanity as your time and circumstances allow. Learn what a different life is like. Learn all that you actually have in common with someone who may seem very different. One, I think it could help your mental health—especially like depression and anxiety, because it busts your mind out of the ruts and routines that make up so much of your day-to-day world.

But the other reason—and maybe related—is that you can learn a lot. Those different sorts of folks than you, those people can expand your mind, get some plasticity going to your brain, loosen you up, and make you forget about yourself for a while, also. I grant you, meeting people like that, I may be at an advantage over you in that my job often involves those people appearing on my show. But I do kind of see part of the duties of my job as being to introduce you to folks you might not otherwise come in contact with, who you will learn from and maybe like.

The show? Ah, yes. It’s Depresh Mode. I’m John Moe. I’m glad you’re here.

Transition: Spirited acoustic guitar.

John Moe: We get a fair number of pitches for our show from publicists who are hoping to get their clients booked on Depresh Mode. Sometimes they’re not a great fit, but sometimes they really are. You’ve heard several guests over the years who have arrived that way through that route. And a few weeks ago, one pitch arrived asking if I’d like to talk with Denise Winkelman. She’s an up-and-coming comedian, they said. Okay, we do some of those. She has her first special coming out on streaming services soon. Okay, great. New comic on the scene; people have invested in her becoming big; there’s a prediction that she’s becoming big. Maybe we book her. Go on, publicist. “She’s also,” the pitch went on, “a former professional wrestler and a trans woman.”

She had spent years giving and receiving body slams and folding chairs to the head. This was before she had transitioned. She deals with chronic pain from fibromyalgia and the effects of concussions. Well, I must say I have never met any trans woman former pro wrestler comedians with chronic pain before. I think we can all learn from that story.

Denise Winkelman’s special is now available on Apple TV+ and Amazon Prime. It’s called Bougie on a Budget.

 

Clip:

Denise Winkelman: There’s a lot of confusion in this room.

(Audience laughs.)

Some of y’all are wondering what the hell kinda of show did I walk into? I am a transgender lesbian.

(Audience cheers.)

Thank you all so much. I’m not a hero.

(Laughter.)

That was a wokeness test. Not everyone passed. I do feel like you should applaud for that, because I paid a lot of money to look like this.

(Laughter and applause.)

 

Transition: Spirited acoustic guitar.

John Moe: Denise Winkelman, welcome to Depresh Mode.

Denise Winkelman: Well, thank you so much for having me. This is gonna be fantastic.

John Moe: I’m here in St. Paul, Minnesota, and I understand that you are a Minnesotan as well. Tell me where you grew up.

Denise Winkelman: Well, I grew up in northern Minnesota, middle of nowhere by Lakes country, but the super cold part. So. (Laughs.)

John Moe: That—okay. Near lakes and where it’s cold. That could be entirely all of Minnesota.

Denise Winkelman: (Chuckling.) It could be, it could be. So, between Bemidji, Minnesota and International Falls, there’s this very small town called Northville, Minnesota. And we live 15 miles outside of that. So, my graduating class— So, it’s a town of 300; graduating class was 18 people. I did not finish in the top 10. So, not a scholar by any means.

(John affirms with a chuckle.)

But very nice place to grow up. It was just really, really cold. So, after college— I graduated from Bemidji State. After college, I headed out. I moved to Cincinnati, lived in Denver for a while, currently in Los Angeles. So, I tend to be getting warmer as I get older.

John Moe: Okay. What—and it’s not often I get a chance to speak to a former professional wrestler. When—did wrestling become a thing early on?

[00:05:00]

I would think while you’re young and strong, that would be the time to do it.

Denise Winkelman: Yeah. So, my background is— I’m transgender. So, much of my life—the early part of my life was trying to fit in. I grew up really religious. And so, a big part of my life—I kind of overcompensated, got really into sports. Which sadly, that stuck. That didn’t go away with transition. So, Big Minnesota fan. I cry a lot.

(John affirms and they chuckle.)

But I still follow sports. And I think I was trying to get fit in but really thought— I remember watching like WWL superstars back in like ‘89/’92. And it was just so colorful, so big. And I just— I got into it as a kid, in ‘96—right around the time I went to college. It was just—it was cool. Like, The Rock, Stone Cold, WCW. Got really into it. And when I get into stuff, like I really go hard at it. And that was the big part of my high school college. Really loved pro wrestling. The internet kind of changed everything, where you could kind of follow all the backstage stuff. And I was like, “Man, this is so cool. I want to do this.”

So, back in 2003— Well, I actually at BSU, Bemidji State, I worked at PBS. ‘Cause my degree—I was a scholar. It was Mass Communications in Television and Radio, because there wasn’t a class that started before 10AM. (Chuckles.) And my evening job was at the local PBS station. And they had a college station where, on Saturday night, they just ran independent wrestling from Nashville, from Georgia. And I just thought it was the coolest stuff. And so, I wrote a handwritten letter and a bunch of emails to places. And Cincinnati was one of the— The Northern Investment Federation responded, and they invited me to come out. At the time, they wanted to take advantage of the camera skills, the background in TV.

But they encouraged me to try wrestling, and I was athletic. I played basketball for a year in a very small Christian school. We played a lot of Canadian teams, and so we won a lot. Which kind of stacks the deck and I’m okay with. But yeah, I got into wrestling, did it for five years—2003 to 2008. Cincinnati is like this underground hotbed of wrestling. It still is. And the place I wrestled, it was very show quality. And so, they would really encourage you to— Promos were a big deal, and I loved the talk. And so, I was a really good promo. I met some really good people, day one. Karl Anderson, who went on to WWE, he was tag team champs there, started the Bullet Club in Japan. He was like one of my best friends, and met him day one of wrestling school.

And he just pulls me aside one day and is like, “This is boring. Like, let’s pop the boys. So, why don’t you just do a promo as like a mad scientist?”

And I was like, “I don’t—I failed science. I’m not good at this.”

(John chuckles.)

I always try to find something I relate to. And so, with this character, I kind of used like the pent-up aggression with, you know, not being able to be myself, feeling really insecure. So, I tried to, you know, kind of lean into those qualities. And then one of the things that I did a lot was I would just do it in a really funny way, and I’d say really intense things, but they’d all be funny. Like, if I were cutting a promo on you, I would be like, “John, you’re driving me crazy, man! Like, you say all these things. Everybody thinks you’re all cute and smart. Well, I’m gonna whip up a potion and turn you into a billy goat.”

John Moe: (Laughs.) Wow, that’s quite a gag! Okay.

Denise Winkelman: Yes, yes. Kentucky, you have to— So, it’s weird, because Kentucky, Indiana, and Ohio were the places I wrestled a lot. Probably did 500 matches during my time there. And so, Kentucky was the unique one. They really liked to talk smack. So, you had to be able to yell at the crowd. And I was good at that. I liked to yell at people.

John Moe: (Chuckles.) And during this time—like, through growing up, through college, and into your wrestling years, you’re still presenting to the world as male then, right?

Denise Winkelman: I really was. And deep down inside, I knew that I was trans.

[00:10:00]

I’ve known since I was four years old.

John Moe: Okay. That’s what I was gonna ask. When did that realization hit?

Denise Winkelman: It was four. And it just was I never felt right in my own skin. And I remember very early on asking my grandma to like knit, to bake. Oddly enough, I can’t do any of that now. But she would actually let me dress up a little bit, but she wouldn’t tell anybody. It was very secretive. And it was something I asked for. And it was really through like Jerry Springer and people like Sally Jessy Raphael. I remember watching Maury one day, and they were doing the “man or woman”, which is just terrible looking back at it. But they were talking about trans.

And it made me realize— I remember sitting down and just being like, “I think that’s what I am.” And it just kind of clicked. And I was about 10 at the time. And I wanted to tell my parents. Like, I had this box of clothes, like old mom’s clothes or my cousin’s clothes. And I wanted to tell my parents that I wanted to transition, but it was the late ‘90s. My dad’s an evangelical—very small-town evangelical pastor. And I just knew it wouldn’t be okay. And I didn’t know what would happen, but I just knew it wasn’t gonna be okay.

John Moe: Did it feel shameful to you or like—? How much of what you grew up with about that evangelical church—did you feel like there was something wrong with you? Or did you just feel like there was this truth about you that you just didn’t want other people to know?

Denise Winkelman: I didn’t feel shameful. Well, part of me felt shameful. It’s a really good question in that sense. I remember just knowing that if people realized this about me or found out, they would look very down on me. And it wouldn’t be okay, and I didn’t know what the result would be. And I felt like the good end would be a conversion camp. And in my parents’ defense, nobody really talked about being trans at the time.

A lot of people didn’t really talk about gay or lesbian, especially up there. They would mention it, but it was something that their belief was that you could just make that go away. And I tried. And I remember lying in bed and badly wanting to tell my parents that I was trans. And I was gonna go do it, and I just laid down and closed my eyes. And I was like, “Well, maybe if I throw myself into sports and try to be really masculine, this will go away.” And you know, I did that all throughout. I would throw myself in this stuff. Everything just felt off. It was always there.

Like, (sighs) I like to say that it’s kind of like having your faucet dripping, where it never stops dripping. Like, you could have a good day, you can do something, but you can always hear that dripping water. Or like where your battery for a fire alarm is going off, where it’s this constant like—you know, it’s constantly there. And my time in wrestling, it taught me a lot. I mean, that was a different version—a straight dude, to be honest. I learned a lot, but I tried to be super masculine. You know, I blended well and nobody knew—to my knowledge. I was also really quiet, really unsure of myself, very soft spoken.

And I think deep down I felt like there was something wrong with me. Because if— The whole thing was I didn’t really connect with people, and I kept everybody at an arm’s distance. In a way, I was kind of a bully. Because humor was my safeguard, and I was very quick, very edgy. But it was kind of like, “Don’t look at me.” And so, I would clap down hard on folks if they clapped on me. You know, that kind of thing. And when I got into wrestling, everybody was kind of like that. There was kind of an insecurity. But—

John Moe: Because you were scared? Is that why you were doing it?

Denise Winkelman: Scared, yeah. And I think you’re just not comfortable wrestling athletically. I think you’re made to feel uncomfortable. And our boss would pit us against each other. One of my friends would always say, “Hey, you know, we’re fake fighting in front of lots of people, but somebody is telling us what to do and giving us the results that we go with. It’s choreographed.” It still hurts, but you know. So, it’s like there’s this insecurity where everybody wants to do more and be better and be one of the main guys.

[00:15:00]

And so, everybody has this thing where it’s like you’d say something in the locker room, and it would just get around to everybody, and all of a sudden people would be gossiping about you, and it was like the worst thing in the world. It had this like small-town vibe. I think the small-town piece of it came into play, because it took me a long time to figure out—when you’re in the city, nobody cares what you’re really doing as long as you’re not hurting people.

What happened was I was dating three women at one time. It was my 24-year-old wrestler on steroids (chuckling), you know, jacked up, trying to be masculine. It was my way to kind of fit in. And I had met a girl; we got married. I was like, “Oh, this will be the next thing.” And when you really get to know somebody and be in a relationship, things start to happen. And little things would come out. And we were married for four years; we were together for six. But little things kept coming out. One day. She was like, “You need to go to therapy and talk about this.” And as soon as I went to therapy, the walls that I built up, they started to poke holes through.

And once they poked a hole in that wall, it just all came out. And I was like, “I can’t get this back in. This has to happen. I have to—” I remember laying down in 2011 or 2012. And I was with my ex. And I was lying in bed. I was not a drinker. And I was looking at this bottle of cheap Jimmy Buffet Margaritaville tequila that we had, and—(correcting herself) not a bucket. But you know, a bottle of it. And I was like, “Well, I can either drink myself to death; I could hurt myself; or I could take a chance to be happy.”

Transition: Spirited acoustic guitar.

John Moe: More with Denise Winkelman on that journey in a moment. And a little later, the mental health effects of all those years getting body slammed and hit with folding chairs.

Transition: Gentle acoustic guitar.

John Moe: Back with comedian, trans woman, former pro wrestler Denise Winkelman. We’ve been talking about how she came to a point where she was choosing between ending her life and transitioning.

Denise Winkelman: And trans was still new. Nobody— People talked about it more, but it still wasn’t super popular. And I was like, “Well, I’m gonna take a chance and try to be happy.” And I’m so glad I did, but it was really hard.

John Moe: When you went into therapy, you had been posing your whole life. I mean, to some extent as a macho athlete, as kind of a towel-snapping wise guy in the wrestling world. And then your job was to present this series of poses as characters—as the mad scientist or whatever, whatever wrestling character you had taken on. And before that—had you ever told anybody before that therapy session that you were trans? That you think that you might be a girl—?

Denise Winkelman: Yeah, I had one—I told one cousin before I moved. And she had to be so confused. Because the way our family was, my uncle was a quarter of a mile down the road from where we grew up. And so, it was me and my brother. My brother’s four years younger. And my two cousins. And my cousins— So, we were all within four years of each other. So…

John Moe: So, you were tight.

Denise Winkelman: We were fairly tight. We were— Yeah, we knew each other really well. And she was like the girl in the family. Right? (Chuckles.) And so, one day she was in college. We like hung out, watched a movie. And what had happened was I was dating this girl. And it was interesting, like—and maybe it was because I was like 20 years old. I was like into it, you know? Like, really into it, even though it kind of felt off. But she would always like tease me like, “I’m gonna dress you up,” or “I’m gonna make you my girl,” or something like that. And it was just enough where, at that time, I was like, “Well, maybe I’m not trans, and maybe this is—you know—gonna be enough.” And so, we broke up—really hard breakup. Like, she cheated on me, all this stuff. So, I was devastated.

And so, then I was like more confused, and I wasn’t going to therapy. But I remember going to my cousin, and it was like this long, awkward car ride conversation where we kept driving around. And finally I just said, “Hey, I think I need to—I think I might be trans,” or “I think I may be different,” or something. And she was really cool. Like, she went shopping with me, which was a big thing early on.

[00:20:00]

And so, she knew. And then right after that, I got more into wrestling, and I decided to move and be a wrestler. And so, for years she was really confused, I think, but she never said anything. And then one day, when I told my parents in 2012— So, I got divorced in October, started hormones in January, and then came out to my parents, you know, probably a month after I got divorced.

John Moe: Wow. So, let me ask you about the therapy though. When you— ‘Cause that sounds like a key moment where the wall falls a little bit, like where you own up to it to the therapist and own up to yourself in the process. At that point, were you presenting as someone else in the therapy session, and did that fall away? Was it still in a pose until that pose collapses?

Denise Winkelman: Yeah, that’s a great question. Just to finish the final thought on my cousin though.

(John affirms.)

Because there was a point to that. With my cousin, when I came out to my parents, she was actually like, “Oh, thank god she finally said something.” (Chuckles.)

And they’re like, “How do you know?!”

And she was like, “I’ve known forever.” (Laughs.)

John Moe: I’ve been carrying this for years.

Denise Winkelman: Yes, yes. So. But with a therapist, it is a really good question. I did not present in therapy at all. I really didn’t present very much until I moved to Denver, and I was working for a financial services company. And I worked one week as male, moved to Denver where they were starting a new site, and I transitioned. So, I presented a little bit, but it wasn’t full-time. And what it was in Cincinnati was I went to this therapy session. We talked about it; it opened the walls. And then that opened more and more, so that I would go to the mall and buy stuff, and then I would— There was this like trans dress up kind of thing where they would take like glamor shots. It was a lingerie store, and she was so nice.

And so, she took some pictures and all this stuff. And I was pretty, and she was very complimentary and was like, “Oh, you could be full time, you could do this.”

And at the time I was like, “Oh my god, that’s great.”

But it took a while, and I probably did that probably three or four times through throughout. I went out a few times. I started going—

John Moe: In Cincinnati, this is?

Denise Winkelman: In Cincinnati. And then there was some trans meetups—like support groups. So, the point of the therapist was, “If you’re gonna transition someday, you have to have a support system.” So, I went to—me and my ex went to the support group. So, back then it was you could go to the cross-dressing support group, or you could go to the trans support group. And I think we went to the trans support group and the next one—and one of the trans women was like, “Oh, you’re a cross dresser.” And I think I was even presenting as male at the time, and they’re like, “We give us six months.” You know? (Chuckling.) And ex didn’t like that at all.

John Moe: Was she your ex by the time she went to this meeting?

Denise Winkelman: No. So, we tried. And we had some couples counseling with a therapist—with the same therapist, I think. And—if I remember right; it’s been a while. I got hit in the head with chairs a lot. (Laughs.) We dated. We tried to make it work. She didn’t want any physical changes. And after a while it was like—I felt really bad. It would almost depress me. Because you dress up, and you put work into this. And it’s like, “Well, I’m just pretending to—I’m just putting this on, and this isn’t who I am.” Like, I don’t want to take this off. This is—I just—this isn’t who I am as a person. This isn’t making me feel right in my own skin.

And so, just dressing up, it was like— I know some people, that’s enough for them. And for me, it was very painful. And after a while I was like, “No, I gotta—I just gotta put the—” And I’m a planner, so I have to plan this out and how to make it work. And I’m so glad I did, but it was a really tough, kind of long road. It took me 30 years of my life to get to that point.

John Moe: Wow. So, you go to Denver, and you walk into the office the first day there, presenting to the world as a woman?

Denise Winkelman: Yep. So, keep in mind this is 2011/2012.

[00:25:00]

So, people were starting to be a little more accepted, and they were starting to try a lot more. Especially, it was a big deal to be on like the HRCs.

John Moe: What are those?

Denise Winkelman: Human rights campaign. Every year they do a diversity index. And San Francisco specifically, they did like a case study with trans benefits and some of those things. And to be listed as a diverse employer or an accepting employer—I forget exactly how they list it. It was a big deal. And so, what happened was I started, you know, kind of planning around it. I talked to my boss in Cincinnati, and he knew I was starting hormones, didn’t tell anybody. And then when I moved to Denver and accepted the job, he helped me craft an email and tell them.

So, I was driving across country. I took a week off. And I didn’t know anybody. Didn’t know anybody. Been to Denver one time. And I went from a campus of 6,000 people at the job where I was working, and Cincinnati guys—mostly guys; it was finance. And then moved to Denver, and it was 75 people day one, because they were starting this site. And it was a lot of leadership, people that had been with the company for a while who they felt could kinda seat the site and help it grow. And it really exploded. I mean, right now it’s over 2,000 people, 10 years later, but—or 13 years later. And it was a really—it ended up being a really good experience.

But I got a phone call from an employee relations vice president. And I didn’t even know we had employee relations, and I had never spoken to a vice president with my company. And knowing the company, it was like a senior national vice president, which was a big thing. And she said she was gonna be my contact through everything, that the leadership team in Denver wanted to do it right. And I was the first person with this company—who had been around since the ‘60s—to ever transition. And she was almost excited. Like, “We finally got one,” you know, kind of thing.

(They chuckle.)

“We’re so excited.” And it put a lot of pressure on me. I put a lot of pressure on myself, but I didn’t wanna turn the company off to what I was doing, and I didn’t wanna make it harder for other trans people.

John Moe: And were you at this point—like, you were doing the hormones, you were on a course, you were heading towards something with what you were doing with yourself.

Denise Winkelman: I knew what it wanted to lead to. And when I moved to Denver, I started living full-time as female. So, I moved to Denver and got the call, met my boss like the week before, like we scheduled a day. I got to meet everybody. And it was a little awkward, because a couple other people from Cincinnati I knew moved, and they were in the room day one. And then when I said my name, they were like, “Ohhh…” I could hear—

John Moe: “It’s not the name we’re used to.”

Denise Winkelman: Exactly. And then it changed in like the employee directory, and I had some people reach out. (Chuckles.) “What’s going on here?” You know? And they were cool, but we never really hung out after that. So, it changed things. But I had a really good experience. I was really lucky. The company—like I said, they wanted to—they treated me really well. I found out later the site general manager told her leadership team that if anybody made me feel uncomfortable in any way, it was gonna be their jobs. So, she was really good about it.

I ended up making a lot of relationships and making a lot of friendships because we were all kind of out of place. It was almost a sitcom. It was the only time in my life where leaders and just, you know, sales associates and religious folks—straight people, gay people, trans—like, we didn’t know anybody else. So, we just all became friends. And I was like, “I’m gonna write a sitcom about this someday.” (Chuckles.) But it was a good experience, and I’m still really tight with a lot of those folks.

Transition: Spirited acoustic guitar.

John Moe: Back in a moment with more from Denise Winkelman.

 

Promo:

Music: Exciting, playful sax.

Jesse Thorn: On Judge John Hodgman, the courtroom is fake, but the disputes are real.

Speaker 1: Brian would say, “I’m the Gumby of this family.” He’s just not!

Jesse Thorn: Claiming to be Gumby is an un-Gumby-like claim.

Brian: No, it’s just Gumby and I being our authentic selves.

(Gavel bang.)

John Hodgman: So, what’s your complaint? Too many sauces?

[00:30:00]

Speaker 2: There are no foods on which to put the sauces.

John Hodgman: Have we named all the sauces on the top shelf yet?

Speaker 3: (Laughing.) Not—not even close.

(Gavel bang.)

John Hodgman: You economize when it comes to pants.

Speaker 4: Truly, it’s not about the cleanliness of the pants.

John Hodgman: Well, why isn’t it?! This is what I want to know!

(Gavel bang.)

John Hogman: Judge John Hodgman. Fake court, weird cases, real justice. On MaximumFun.org, YouTube, and everywhere you get podcasts.

 

Promo:

Jordan Morris: It’s hard to explain what Jordan, Jesse, Go! is about.

Jesse Thorn: So, I had my kids take a stab at it.

Kid 1: Probably weird stuff.

Kid 2: You talk about—

Kid 3: (Interrupting.) Jobs that are annoying!

Kid 2: Mm. Business.

Kid 1: I think you probably learned your lesson after talking about business a couple of times.

Kid 3: Grownup jokes that I don’t understand and there’s no point making and—

(They giggle.)

All the podcasts go away.

Jordan Morris: Subscribe to Jordan, Jesse, Go!

Jesse Thorn: A comedy show for grownups.

 

Transition: Gentle acoustic guitar.

John Moe: Back talking with Denise Winkelman. We talk about fibromyalgia coming up in this interview. Fibromyalgia is a chronic condition often caused by a physically traumatic event that involves pain all over the body as well as fatigue. It’s been linked to depression, anxiety, severe headaches. There is no cure, but some people have success with medications and therapy.

You referenced being hit by chairs a lot, which is a natural thing that happens in the industry that you are in as a wrestler. And I understand that you’ve had some long-term health problems with fibromyalgia, with post-concussion syndrome. Was that a result of the time you spent as a wrestler?

Denise Winkelman: Yeah, I think a lot of it is. I’ve never had a diagnosed concussion, but I know I’ve had some. Well, I’ve had my bell rung several times. I also know I had one. I was in a— I was reffing early on in, in my wrestling career. And I’m gonna say the name; it was Wildcat Chris Harris, who had some fame for many years just underneath WWE in a promotion called TNA. And he was like the big star that had come out of the promotion right before me. And big, good-looking dude, and tag team champs. And he was coming back and doing a big run. It was a big deal. And we had like 200 people. And I had been in wrestling training for like six months, and they had me being a referee. And it was like this main event and one of their big shows.

And we were doing the spot where I told him—like, I didn’t see him win, and I took the belt away from him or something. And then he was gonna clothesline me. And he really clotheslined me. And we talk about politics in wrestling or insecurity. It turns out my friends had really kind of thrown me under the bus, ’cause they thought it was funny. And they were like, “No, you gotta really hit Winkelman. You gotta really hit Winkelman. They’re not gonna sell it for you.” And so, the guy just clotheslined the crap out of me. And I hit the back of my head. And it’s not his fault, but I had never been clotheslined like that before. And I know it messed me up for about a month. So, that was the first one. I had seen stars many times.

And then the last part where I really started to get out of wrestling. One of my friends, we were doing this main event show, and my friend body slammed me on the concrete. And you always hit your friends harder in wrestling, because you know they can take it. And I had never been body slammed on the concrete before, and it was the most painful thing in my entire life. I think it—it messed my back up, but I think it really messed my neck up as well. So, it all kind of played a part into it.

And I think years later—like, I had— (Sighs.) It’s weird, because I think I had always had a form of fibro. Like, I would go really, really hard in wrestling. I would do months at a time where I was working day job; I would work out, go to training or wrestle a show. And you know, we’re in our 20s. My buddies would go to the bar after, and a lot of times I would too. And whatever else debauchery we could find. And it was all the time. And we weren’t getting tons of sleep. But then I would hit this wall, and I would sleep for three days. And that’s kind of how I’ve always been since then is I would have these periods where I just would work really hard on a project, go really hard, be exhausted.

[00:35:00]

And then it would take me several months to get to that point where I could just go hard. And 2018/2019, I was starting to have a lot more pain in my body. My leg—

John Moe: This was after wrestling was done.

(Denise confirms.)

Okay. What year did you stop wrestling?

Denise Winkelman: I finished in 2008.

John Moe: Oh, okay. So, this was years—this was a decade later.

Denise Winkelman: A decade later. I did it for about six months in 2016 in Denver. It just hurt too much, and I was getting way too many migraines at the time. I also realized that I was probably self-diagnosed and self-medicating a lot. And one of my—(chuckles softly). I have a funny story about hormones. Remind me to tell you about it. But my primary care doctor saw how much ibuprofen I was taking, and she prescribed some diclofenac, which was like a prescription ibuprofen and was like, “Hey, you need to—let’s get this—you know, like let’s look at different options to not ruin your stomach.” And so, she had me go to a neurologist, and I’ve been working on that ever since.

But 2018/2019, I got to be a lot worse. I started having a knot in my shoulder that I just couldn’t get rid of, and the migraines would go through the back of my head. I would have them every day. And when I moved to Los Angeles in 2020, they were a little better just ’cause I wasn’t doing a lot, nobody was really doing a lot. But when things opened back up, I kind of was working a day job at the time and, you know, just going with comedy really hard. It was tough. And I would have the—it started the—I remember I was going so hard. I was working out all the time, ’cause I wanted to be pretty, and I was really overdoing it athletically. But I would just never smile.

And I was doing comedy, and it should be fun. And I would write material, and like I’d be in pain all the time, and I’d be miserable at these shows. And I was like, “I don’t know what’s going on.” And so, in 2022/2023 I did a ton of doctor’s appointments. And they determined—you know, fibromyalgia is what they called it. But I’m still trying to figure it out, still trying to manage it. But you know, brain fog, pain, migraines, you know. And you just never know when it’s gonna hit. You know, I would go out and do a mic or do a show, and all of a sudden—you know—at the end of the night, I would just have like this killer headache and really low energy. And so, it’s better now, but it took a long time to be able to figure that out.

John Moe: What were the mental health effects that got triggered by the chronic pain—from the fibromyalgia, from all these things? How did that manifest in your mental health?

Denise Winkelman: Yeah. So, for me it’s stress. And that’s one thing I’ve learned. The biggest trigger is stress for me. So. And I’m someone— I’m a go-getter. What usually would happen—and this has been a constant cycle for me—is I would take on a lot, or I would take on a couple things, and I would feel good. And then I would take on more, and then have the day job on top of it, and I could manage it. But then as I took on more, I had more on my plate, more outside of work, and I didn’t have a lot of space to breathe. And it would lead to depression—like mood swings, a lot of pain. You know, a lot of times I would be really flaky. I would cancel my plans with people. I would book a lot, and then I would cancel two things or three things, because I would have a migraine.

The stress was the biggest trigger that I learned. And it’s hard, because it’s hard not—can you imagine not having stress in your life? It’s nearly impossible. And with the special, I put a ton of work into it and recorded it. And that’s the goal. The goal was always to live on comedy. And the industry has changed and all of that. But I realized it was almost like Will Smith in Pursuit of Happiness where all the kids were working 12 hours a day, and he was like, “Well, I got a kid. I’m homeless. I can’t work 12 hours a day. I have to figure out a way to work smarter.” And I realized in my 40s, nobody was gonna tap me on the shoulder and say I’m funny. (Chuckles.)

They could do that, but nobody was gonna be like, “Hey—” ‘Cause you gotta hustle in comedy. And I’m not the sort of person—I can’t be at the club every night, because of fibro. So, I’m gonna have to figure out a way to do it myself. And that was the reason I put a lot of work into the special. So glad that it’s paying off.

[00:40:00]

But I just wanted to do something I was proud of.

John Moe: And so, when did the comedy start in this timeline? So, you leave Cincinnati, you go to Denver, you’re identifying as a woman, you’re transitioning. When did the comedy start?

Denise Winkelman: So, I went through a lot of surgeries. My goal when I transitioned— Because I would hear these horror stories with, you know, people being beat up on a bus or, you know, being outed like in a restroom. And it’s really dangerous. And I realized when I transitioned and that I went from a White, straight male to a female. And my odds—as a trans woman, my odds of being hurt or something bad happening just went [up].

And thankfully, nothing happened. Nothing bad happened to me. But I know people that it has happened to. So, 2013/2014, I did a lot of surgeries. 2016 was like the final surgery. And after that, I was looking for like an outlet creatively. So, I wrestled for six months. It hurt too much. I was getting way too many migraines. And I’m like, “I can’t hustle at this. Like, just where I’m at right now.” And I needed a creative outlet.

My friend told me—like, even in high school, people would tell me, “Hey, you should be a standup.” And I always loved standup. It was kind of the same thing with wrestling, but I chose wrestling at the time, because I just thought— I was just so into it.

John Moe: There’s a lot of comedy performance in both, I suppose.

Denise Winkelman: Comedy in both, and it’s a live performance. So, you have a lot of creative freedom. When I was doing wrestling the first time, like nothing was scripted as far as promos. So, I could write my own promos. I could, you know, do a lot of that stuff. So, it gave me a big creative outlet. And I’m somebody creatively that I need to constantly be growing to feel fulfilled. And so, I was like, “No, I’m gonna do standup.” And that seems like something I can control. I can write; I can do the image that I wanna do.

And my first time on stage was with the Gender Center in Denver. I told some people there I was thinking of standup. They gave me eight minutes, which is a long time, in front of 300 people at a fundraiser.

John Moe: Wow. That’s a lot!

Denise Winkelman: I worked a ton on it. I had never done a mic before, so I’d never done comedy in any way. And I got enough laughs. I was really nervous. I shook the mic and stuff. But I got way more laughs than most first-time performers and got enough where it was like, “Okay, I need to do this more. And this is it.”

John Moe: When did you move to LA?

Denise Winkelman: 2020. I moved two weeks before the pandemic shutdown.

John Moe: (Chuckling and drawing a breath through his teeth.) Oh boy. Ugh!

Denise Winkelman: Timing is everything. What kept me in LA was we had written a script at the time, called The Authentic Step. Really proud of it. It won awards and festivals. It never got picked up, but we put a lot of work into it, and we were gonna shop it. And so, I moved with a friend, and then we were just shut down for two—you know, almost a year and a half.

And the good thing about it was I met a lot of comics on Zoom. I started working a lot on Zoom, doing a lot of Zoom sets. And I met all these people. So, when everything opened up, I knew a lot of comics at the time. So, I would go to these shows, and I would know everyone. So, it was a good thing to do, but a really tough start.

John Moe: How do you handle all the stress now? Because it seems like you’re managing some of these injuries, these physical injuries that you had from earlier. You have stress as a trigger for other mental health conditions. And I feel you on that. I have that same thing, and it’s a bear to manage sometimes. And then you are in this industry that can be very competitive to try to even get anyone to see you, let alone make a good living doing it. And on top of that, you’ve got the stress of being a trans woman in the political climate of 2025, when a lot of horrible people are doing a lot of horrible things around the trans community. Like, how do you take care of yourself right now?

Denise Winkelman: It is not perfect. I would be lying if I said it was perfect. The day job, when I have worked a day job— I ended up taking time off just so I could focus on comedy. And hopefully it’s a permanent thing, but I really wanted to maximize it. But I got to a point where the day job was asking more and more.

[00:45:00]

And I could barely do comedy at that point, just because I wasn’t in a space creatively to do it. A lot of people in this business will waste your time. They will either take your money— You know, LA, it’s all about filling seats. And a lot of—even people with specials, even people with a big following can’t fill a room in LA, because there’s comedy on every corner. (Chuckles.) So, it’s a tough place to do it, and I’m not gonna be a person that goes and hangs out at the club all the time. Being able to go and support and be around, I found, is helpful. Focusing on the things that make me happy is really important.

So, being around people I like. I try to avoid as much bad comedy as I can. I realized, when I was really miserable, I was doing too much comedy-wise. I was seeing way too much bad comedy. And I was like, “Man, I need to just see people that inspire me, and then do it in a way that works for me.” I’ve always been somebody that, if everybody else is doing one thing one way—and that’s the only way you can make it, that’s the only way you can do it—well, let me find what works for me. Because I just don’t think it’s healthy. And if we’re all trying to do the same thing, and it’s not working for anybody, there’s just too many people doing that.

So, for me, it was doing the special, kind of creating that, trying to use it to get my name out there and get a really good credit, but then also get enough fan support where I can go out of town and tour on my terms. I’m probably never gonna be like a Burt Kreischer that’s doing, you know, 27 shows every night. You know, it’ll probably be one or two. You know, balancing between. And if I know it’s coming up—you know, I’m much better at that and planning the day.

But it’s when the little things come up. Social media comes up. “Hey, you gotta post something.” Or— I love doing interviews, but you know, having that the day of the show or having that—you know—and making sure I have time to properly get in the right mindset. You know, like get ready, get prepared, trying to eat better. Even though I eat like I should have diabetes (unclear) time. I stress eat. And so, that’s a problem. But you know, trying to do some of the little things to— And I think it just comes down to “focus on what makes you happy.”

John Moe: You mentioned seeing people—comedians who inspire you. And you must have been that comedian for some other people, especially people in the trans community, people who can kind of feel what you’ve been going through. Have people approached you and talked about what your comedy has meant to them?

Denise Winkelman: Yeah, they have, and I expect that to continue. Even early on, the first few years I was on stage, I never talked about being trans. And the last several years, I’ve been very open about it on stage. But I was also doing fitness modeling at the time. And when I was fitness modeling— Somebody in the wrestling business told me I wasn’t pretty. And I was like, “Well, screw you. (Chuckling.) Fuck you, man. Like, I’m gonna go—” And so, I did modeling for two years as well. And I had lost a job because they found out I was trans. And so, when I lost that job, I decided not to talk about it for the first two years.

When I started being real and being open about it, even the straight male comics who definitely weren’t supportive of trans, they laughed so hard. And they were like, “That was hilarious, and that was real.” Ralph Porter pulled me aside one night. I opened for Ralph Porter, a fairly big-name comic. Really funny. Really funny. He was like, “I am so proud of you.” It was my first time ever talking about being trans onstage. And he goes, “You were real. And we had to change the lineup because you were so funny and real.” And he was like, “Nobody else could follow you.”

But what I found is a lot of people after shows would come up to me or message me and say, “Hey Denise, I have a trans kid,” or “somebody in my family,” or “I know somebody who’s trans, and they really struggle with the stuff you were talking about. But I learned so much.” And even people not in the community. Just “I learned so much about—it’s almost like a TEDtalk mixed with what you do and being funny. And that means a lot, because just you being onstage and representing it, it means a lot.” I’ve also found it with fibromyalgia. I talk about fibro on stage in the special, and a lot of people have said, “Hey, have you tried this?” Or “I know this person with fibro, and it’s really brutal.”

[00:50:00]

So, I’ve always been a big fan of being real onstage, being funny about things. Not that everything has to be real, but you know, why not talk about real stuff, you know? And try to make it funny. But it is a little awkward, you know, just being like, “Hey, I inspire all these people.” But I think just being real—especially right now—and being honest about the experience, and talking about background and some of the struggles I do think has inspired a lot of people. At least what they’ve shared with me. So, I’m really proud of that.

John Moe: And I think a lot of people don’t understand the connection between chronic pain, fibromyalgia, and mental health. People say, “Oh, you have chronic pain. That means you’re in pain all the time. That’s too bad.” But it’s more than a physical thing. It affects every aspect of your mental health and how you live with your mind. Right?

Denise Winkelman: Oh, 100%. 100%. Because you know, a big part of this is I wanna do more. I wanna do more comedy. I wanna be one of those comics that are out there all the time. I want to be writing, and I want to feel good. And when that doesn’t happen and, you know, a migraine hits or a body pain hits, and all of a sudden the mood change. And I have to honor my obligations, but it might not be the best version of myself. And it can lead—it does lead to depression. And there have been many, you know, weeks at a time where I’ve had to not cancel appearances, but just cancel things that I had planned and not be— It is like, hey, I’m by myself in Los Angeles, a very lonely place anyway, trying to do this. And I’m not able to get off my couch for weeks at a time.

Music: “Building Wings” by Rhett Miller, an up-tempo acoustic guitar song. The music continues quietly under the dialogue.

John Moe: Denise Winkelman, thank you so much.

Denise Winkelman: Absolutely. Thanks so much for having me.

John Moe: Denise Winkelman’s special, Bougie on a Budget, is available now on Apple TV+ and Amazon Prime.

On our show page, we have some links to some fun Twin Cities things you can do with me this fall. My band, Math Emergency, plays its final show September 21st. Wits returns to the Fitzgerald Theater on September 30^th. And I’m teaching writing classes all fall at the Loft Literary Center. So, check out those links if you are anywhere near the Twin Cities.

Our show exists because people help fund our show. These interesting people, these people you wouldn’t ordinarily meet, perhaps, coming into the speakers in your car, or into your headphones, or in the little player in your kitchen—that takes money. Making the show takes money. We ask you to support it. A lot of you have, and thank you so much. If you haven’t already, please do. We really need it. This is the only way we really operate. Just go to MaximumFun.org/join. Find a level that works for you—maybe it’s 5 bucks a month, maybe 10, 20, whatever makes sense for you—and support the show. We really need it, and we really appreciate it. Be sure to hit subscribe. Give us five stars. Write rave reviews. That gets the show out into the world.

The 988 Suicide and Crisis Lifeline can be reached in the US and Canada by calling or texting 988. It’s free. It’s available 24/7. We’re on BlueSky at @DepreshMode. Our Instagram is @DepreshPod. Our Depresh Mode newsletter is on Substack. Search that up. I’m on BlueSky and Instagram at @JohnMoe. Join our Preshies group on Facebook. A lot of people helping each other out there—sort of supporting each other, making some jokes, talking about mental health, talking about the show. I’m there too. I’ll see you over there. Just go to Facebook, search up Preshies. You’ll find it. Our electric mail address is DepreshMode@MaximumFun.org.

Hi, credit listeners. If you go to the Minnesota State Fair—which is going on now—you may want to stop by The Mouth Trap. I’m not lisping. That’s the name. Mouth Trap. A little picture of a mouse there. They sell cheese curds, and they go through 65,000 pounds of cheese each year during the fair to make all those curds. They are good curds! Though I actually prefer the jalapeno curds at Miller’s. That’s over by the giant slide.

Depresh Mode is made possible by your contributions. Our production team includes Raghu Manavalan, Kevin Ferguson, and me. We get booking help from Mara Davis. Rhett Miller wrote and performed our theme song, “Building Wings”. Depresh Mode is a production of Maximum Fun and Poputchik. I’m John Moe. Bye now.

 

Music: “Building Wings” by Rhett Miller.

I’m always falling off of cliffs, now

Building wings on the way down

I am figuring things out

Building wings, building wings, building wings

[00:55:00]

No one knows the reason

Maybe there’s no reason

I just keep believing

No one knows the answer

Maybe there’s no answer

I just keep on dancing

(Music continues under the dialogue.)

 

Lynn: I’m Lynn from Portland, Oregon, and I believe in you. And here’s the second one.

(Music fades out.)

Transition: Cheerful ukulele chord.

Speaker 1: Maximum Fun.

Speaker 2: A worker-owned network.

Speaker 3: Of artist owned shows.

Speaker 4: Supported—

Speaker 5: —directly—

Speaker 6: —by you!

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