Peppermint on Her New Comedy Special, Trans Dating, and the Best of New York Drag

Most drag performers are multi-hyphenates, but few are as successful in their various hyphenates as Peppermint. Since placing second on season nine of RuPaul’s Drag Race, Peppermint has originated a role in the Broadway show Head Over Heels, appeared on multiple TV shows including Pose and God Friended Me, released her second album and four EPs, wrote and starred in a short film based on one of those EPs, co-led the drag competition show Call Me Mother, and now has just released her first comedy special, So-SIGH-ety Effects. Her singing voice — well-suited for both showtunes and sexy, sexy R&B — is matched only by her political voice. Peppermint is an artist who takes her platform seriously, a model of talent and community care.

I was lucky enough to talk to Peppermint about her new special, the ever-exhausting topic of dating while trans, and the many ways Broadway needs to evolve.


Peppermint: I’m so sorry I’m late!

Drew: That’s totally okay. If there are two things I know, it’s LA traffic and working late on a Joey Soloway project so whichever one of those it was is understandable. (laughs)

Peppermint: Both. (laughs)

Drew: So you’re in LA right now rehearsing for the Transparent musical. Where are you at in that process?

Peppermint: Just a few days into rehearsals for the production.

Drew: Oh wow!

Peppermint: The project is obviously inspired by the TV show, and it’s been in the minds of a few folks for years now. They’ve been focusing on this production for about a year, and the past couple of months there have been a few workshops. But we’re only a few days into working with the cast that will be performing it this summer.

Drew: You also originated your role in Head Over Heels. What’s the difference between originating a role and just being cast in a production. Because you have also played Angel in Rent, right?

Peppermint: Yes! I mean, it wasn’t even a regional production. It was a community theatre production that was part of a one-act festival in Wilmington, Delaware. With Aubrey Plaza of all people!

Drew: Oh my God!

Peppermint: Among lots of other fabulous people. Delaware, you know, we have some folks.

But I don’t have that much experience to compare originating vs. not, because doing a show on Broadway and doing a community theatre production are so different in other ways. That said, being able to breathe life into a character that has already been performed before allows a lot of source material and sometimes even inspiration. With something like Rent, I didn’t have to do that much studying for the character. This was back in the 90s, about a year after the show had opened on Broadway, so it was fresh on everybody’s mind. I was a fan of the show. Everybody was.

That’s one of the things originating doesn’t provide. You just have your imagination and whatever the text gives you. But then logistically for theatre, before it can get to Broadway or be professionally produced, it has to go through readings and workshops, which is hours and hours of time, thought, consideration, trial and error, experimentation, rehearsal, rehearsal, rehearsal, rehearsal, and editing. A song has the same music but completely different words, oh we’re putting the words back in but now it’s a rock song. That doesn’t happen if you’re just going to do a guest spot or what they call “the celebrity track” in a Broadway show that’s been running for many years. Also there’s an element that I’ll be associated with, let’s say, Head Over Heels, for a long time even if I’m not doing it.

Drew: Do you have classic Broadway roles that you dream of doing or do you prefer to focus on new work?

Peppermint: No, I don’t have classic Broadway roles I want to do. Of course, there are roles if someone offered me the opportunity and money — money! — to do, I’d consider it. I mean, I love performing on the stage. But I think professional theatre has a lot of catching up to do with the racial and ethical reckoning we’ve had over the past few years. The producers are starting to understand that there’s an adjustment that needs to be made, the casting directors are understanding it. But the gatekeepers are still keeping a lot of the writing out. All we have are these mainstay theatrical productions that never have room for people like me. So I never imagined myself in those shows. And they didn’t imagine me either.

I remember being told by one of my professors in college that I was great but that there was no work for me so I should save myself the trouble and go do something else. And I did. So no, there aren’t any roles I can see myself in or want to see myself in. Because with these older productions that are still hanging around, making somebody money, a lot of them still have problematic content in them. So we have to figure out the casting and we have to figure out the content. And, you know, that producer said a couple years ago that trans people can’t do Broadway because it’s just a gimmick and we shouldn’t rewrite the classics. So if that’s how they feel, then no. I don’t want to bring my energy to a production like that, because a show takes a lot of energy and time and care. I say, let those old relics die.

Drew: I appreciate you bringing up the text as well. Because a lot of the producers who are willing to cast more inclusively aren’t willing to engage with what that casting means for the show or make changes to the text in ways that would service that version. Even if they’re willing to plop certain actors in, which is great from an employment standpoint, it’s not meaningfully changing the work in a way that’s needed.

Peppermint: Or even the music!

Drew: Yeah! That’s real.

Peppermint: The keys. I heard through the grapevine about a popular show that closed last year and one of the administrators said they wanted to cast somebody who is trans but they didn’t want to touch anything about the show. They don’t even want to change the keys. And okay, sure, they want to find somebody who fits the bill, but there’s a reason why some of these things need to change to actually be inclusive. If they wanted to cast somebody who is voluptuous or bigger in a role that’s previously been played by thin people, they’re going to have to change the costume! You can’t just expect somebody to fit in the same thing. So it’s the same with the music and the text.

Drew: Absolutely. Thank you for saying that.

Switching to your special, what was the writing process like for So-SIGH-ety Effects?

Peppermint: It was actually really amazing. It was like a crash course in comedy. As a drag entertainer, I’ve always used comedy in my shows, but I certainly don’t consider myself a comedy act. I don’t think most people would. And while I understand the technical aspects of comedy and that world, doing a comedy special was far down the list of things I was going to propose. So when Comedy Dynamics approached me about it, I was honestly like, me? Really? But the writing was on the wall over the past couple of years that we would be in this moment legislatively with regards to anti-LGBT sentiment and anti-drag sentiment. So I wanted to take the opportunity to tell our stories, tell my story, tell a trans story. And I know that people learn best while laughing. Audiences need more trans comics. There certainly are a handful of well-known trans comics, but we need more. So that was my inspiration.

One of the things that was important to me was being able to tell something that felt authentic. And I believe I did that. I just told some wackadoodle stories about things that have happened to me as a trans person navigating everything from bathrooms to jobs to love to family. There are plenty of stories that can be looked at through a comedic lens, so that’s what we did.

I got together with Kellye Howard who’s a brilliant comic out of Chicago. We actually wrote it together while I was in Canada filming Call Me Mother, and then she met me in New York and we finished it and finetuned it in about a week. That’s very short for a comedy special. Most of the comics we know and love workshop their material for months if not a year. But we didn’t have that kind of time.

I’m really grateful that I was able to do it. It was a great experience. The folks at Comedy Dynamics along with the Producer Entertainment Group were a wonderful bunch to work with. I hope people like it!

Audiences need more trans comics. There certainly are a handful of well-known trans comics, but we need more. So that was my inspiration.

Drew: I think you do a really good job at finding humor in some pretty harsh things. Like the guy who goes full Crying Game vomiting after a hookup. It’s the sort of thing that can inspire pity, and instead you inspire laughs.

Peppermint: Yeah, I mean, these things happen, and many of these stories in the moment feel really depressing. But then, sitting around with my girlfriends, we laugh about it. We’re like, “Girl, can you believe this. You went through it too? Same guy??”

Drew: (laughs)

Peppermint: Then we really have to laugh.

Drew: Speaking of dating, you’ve toured around the world, and you even talk about finding love in Ireland. When you’re on tour are you on the apps in different cities? Have you found that dating as a trans woman varies in different cities and different countries?

Peppermint: Yes. I think the starkest differences are state to state. Even though I’ve obviously been to other countries and enjoyed the wares.

I mean, let’s be real, the message has been sent that the men around are not looking to wife a trans woman. I’m not saying that none of them are, but it’s obvious there are challenges being trans and dating. Even just having to disclose and explain something about your trans existence and how it might fit into their world in terms of dating or even sex. So I go onto the apps with a grain of salt. I’m not looking for no husband if I’m up in Schenectady for two days.

Drew: (laughs) Sure.

Peppermint: (laughs) That being said, I actually met the Irish guy while I was in the States. So it just so happened that I got to a place in my career where I was able to travel the world. And I’ve had a handful of long distance relationships since then. I’m actually in a long distance situationship right now, which we’ll see how that goes. And that’s only because I left New York and am in Los Angeles. Quite temporarily. But it has been a challenge. I know there are some dating apps that have been around for years that are more LGBT friendly. There are a couple of new dating apps that are trans-focused that I’ve used the least for obvious reasons. Or at least obvious for people who are trans. But I do have high hopes, despite what we’re facing. I know the message being sent out by lawmakers probably sends a message to our potential partners that we aren’t desirable sociably. So that’s a bump in the road, but I do think it’s inevitable that we will be fully included and immersed in the world of dating. Then we’ll just be able to deal with the BS cis women deal with — which we already do, of course.

Drew: Do you feel like you’re able to tell the difference between regular challenges of dating and trans-specific challenges? That’s something I’ve struggled with over the years. Trying to learn to not take everything on as related to transness. Trying to let go of that assumption, because sometimes dating just sucks for everybody. I mean, sometimes it’s obviously transphobic because they’ll say. But with the rest, are you able to tell the difference?

Peppermint: I don’t know that I am. I mean, obviously when something is ending all you have is speculation. If you have someone who is well-spoken, emotionally available, and invested in having good communication at all stages of the relationship, then you’ll probably be able to tell the difference. Sadly, I don’t think most cisgender men carry those characteristics very well, so if that’s who you’re dating then you’re left wondering what’s happening and filling in the blanks for your damn self. But I was relieved that my most significant recent breakup, we did break up for what I believe to be normal everyday relationship things. And he and I are still friends to this day. We broke up right before the pandemic and parted ways for a couple years, but now we have a newer friendship. And that’s because, as young as he was, he was really invested in good communication. I can only speak, sadly, as a heterosexual, but hopefully men in this new age — cis or trans — will engage with being better partners.

Drew: I really like what you say in the special about trans people being forced to be more mature. So often in cultural rhetoric, there’s this idea of trans people having a second puberty and being immature. But that’s so focused on the early months and years of transition as if we don’t, hopefully, live long lives after that. I really appreciated you saying that, because I’m not sure I’ve ever heard anyone say actually because of the shit we have to deal with we’re possibly more mature.

Peppermint: Yeah, I certainly believe it. I mean, I’ve met some immature trans folks and I’m like… girl… honey. But I even think that can sometimes be people projecting how they want to be perceived whether it’s ditzy or just not making good choices. Anyway, there are all sorts of people all around the world, so, of course, I’m generalizing.

Dr. Angela Davis said something that really connects with my feelings about trans people going through certain experiences. I’m paraphrasing, but she says that trans people can show us what it means to live fully in the human experience without being held back by the gender binary, the sex binary, the sexuality binary, that we operate in as a society. That’s the way of the future. Being less constricted by these things. And trans people are already doing that. Not all, but many of us in the movement are. And that gives me hope for the future. There were times where trans people, nonbinary people, gender nonconforming people, were elevated to a point of reverence in cultural and religious circles historically in the Americas, in Europe, in South America, in India, all over. If society was able to see those people as elevated and anointed in a way then maybe society will get back around to that.

Drew: You talk about trans people and you specifically being on high alert for danger. How do you find a balance between being prepared in order to protect yourself while not living in a constant state of anxiety?

Peppermint: I mean, a lot of that probably also connects to me being a New Yorker. (laughs)

Drew: I transitioned while I was in New York and spent my first years there so…

Peppermint: So you get it.

Drew: Yes.

Peppermint: And this actually brings us back to dating in different areas. Because this is where I’m stuck. On the one hand, I do want a progressive, forward-thinking partner. But on the other hand, a good ol’ traditional moment can sometimes be appreciated. Sometimes you meet guys in the midwest or in the south who aren’t prejudiced or discriminatory and want to open the door for their trans partner, are okay going on a date before expecting sex, all of those things that are part of courtship, I’m not saying those things don’t happen in places like LA and New York, but the guys in LA and New York know what they want and know the terminology and oftentimes just want to cut to the chase and get what they’re going to get. So that’s an interesting dichotomy.

In regards to being on high alert, I often speak about and use my platform to shine a light on the violence trans people face globally and in the country, the discrimination that LGBTQ people face. I try my best to use my platform to talk about that in a way that will allow the rest of the society to see how their microaggressions and biases and how society in general perpetuates that discriminatory treatment and violence. It’s important for me to talk about those things. But now that I’ve been on television and have been able to get to a certain point in my career, I’m lucky that I’m not confronted with those things as often as many other people. So even if I’m not on high alert like I used to be, I want to highlight that there are people who are in that situation. I don’t like to focus on medical transition, but that can play a part in how people perceive you especially when mid-medical transition. I certainly experienced that myself. And so even if I’m further along in my journey, it’s important for me to advocate for those who are less far along if they’re going to medical transition or even socially transition in a way that allows other people to judge and discriminate against them. But I’m grateful that now I don’t walk through the streets fearing for my life.

Drew: You open the special with your song “Best Sex” from your 2020 EP, and I wanted to talk about the short film you made to coincide with that EP. I saw April Maxey’s film Work when I was on the Outfest jury last summer and I think she’s so talented. How did the Girl Like Me film come about and what was that collaboration like?

Peppermint: It was written because of the pandemic and how the world became. I knew that I wanted to do some music videos for the EP but we didn’t know how to do that given the moment. Like were we really going to fly back and forth and make videos for all these songs? So we decided to just get everybody together, test them, film in a week, and do it all at once. Because this was 2020.

We were looking for a director and we ended up meeting April through some people on my team and April was wonderful. I loved working with her. We were initially going to have her back for part two but she had to move onto another project and it didn’t work out with scheduling. We are currently fine-tuning and finalizing part two right now though.

Drew: Oh that’s so exciting!

Peppermint: Yeah!

Drew: Before we go, I’m purposefully not asking you any questions about Drag Race or about how Drag Race has evolved in terms of trans performers or why it took so long, because I’ll save that for if I ever talk to RuPaul or any of the execs at World of Wonder. That’s not your business.

Peppermint: Thank you very much.

Drew: But we are talking a few days after Sasha Colby was crowned. And I just, honestly, wanted to thank you, because I do think you being on the show when you were and dealing with all the bullshit that came along with that has allowed the show to be where it is now. So I don’t have any questions about Drag Race, but I did want to just note that for our readers and thank you for putting up with whatever the challenges were of that visibility and that moment in time.

Peppermint: Thank you. I appreciate that. There were some challenges. I’m grateful for my time on the show. I’m so excited and happy for Sasha. She’s obviously very skilled and very professional. She’s definitely my kind of drag entertainer. So I’m really happy for her. And, honestly, I’m really happy for the top four that made it to the finale. I remember how terrifying it was for our group. And I did feel an added pressure being trans on the show, how would the community receive it, how would the world receive it, how would the show handle it. And for the most part, I had an experience that I’m grateful for. And I’m grateful for the things that I’ve been able to do since the show. I hope I made an impact somehow.

Drew: Something I also feel very strongly about is that there’s a whole world of drag outside of RuPaul’s Drag Race. So I did also want to take a moment to ask, are there any drag performers or drag bars that you want to shout out?

Peppermint: Certainly, I believe that people should go to New York City, and even though there’s been all this talk about how the world has changed and New York isn’t the same and this and that, New York is still a wonderful city because it attracts so many different types of people with so many different skill sets. We all mix and mingle with each other, along with our talents, our careers, our conversations, in a way that in other cities you don’t necessarily get to do, because people just drive in or drive out. But in New York, you’re just in really close proximity to people, including in the drag performer scene. I think I had a really singular view of drag performers before I moved to New York City. And then in New York, I met people who were wonderful performers, great vocalists, and I’m talking 20 years ago when the definition of drag was just lip syncing. I also met drag queens who were legit models and didn’t even perform. They wouldn’t go to the stage, they’d just stand and look gorgeous. Obviously Drag Race has touched upon some of the archetypes of drag, but there are so many more.

There are some girls who I’m really loving right now in New York, and they aren’t even the newest girls. But they are New Yorkers. Pixie Aventura is a brilliant drag entertainer in New York. I also love Bootsie Lefaris. She is wildly inappropriate and such a kook and just wrong in every way that’s just right. And then there’s another performer — people might not think she’s a drag entertainer but I would say she is — Narcissister who mixes the worlds of burlesque, performance art, and drag. She’s fantastic. So people should check out those three folks. I’m sure they have stuff online and then when you come to New York you should see them.

Drew: I love how much you love New York. I love it too. Whenever I’m not there, I miss it.

Peppermint: Me too. I’ve only been gone for a few days and I’m already like get me the fuck back there.

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Drew Burnett Gregory

Drew is a Brooklyn-based writer, filmmaker, and theatremaker. She is a Senior Editor at Autostraddle with a focus in film and television, sex and dating, and politics. Her writing can also be found at Bright Wall/Dark Room, Cosmopolitan UK, Refinery29, Into, them, and Knock LA. She was a 2022 Outfest Screenwriting Lab Notable Writer and a 2023 Lambda Literary Screenwriting Fellow. She is currently working on a million film and TV projects mostly about queer trans women. Find her on Twitter and Instagram.

Drew Burnett has written 567 articles for us.

3 Comments

  1. Terrific interview! Though, wow, I’ll tell ya, reading her comments on dating makes me very glad to be a lesbian–women seem way more willing to wife a trans woman than men do.

    (I mean, at the very least, my wife certainly was!)

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