After Hyping Madonna, Bob the Drag Queen Kicks Off a World Comedy Tour

Stand-up comedian, stage actor, drag queen, Madonna’s hype person, podcaster, rapper — is there anything Bob the Drag queen can’t do? The all-star entertainer catapulted into the limelight in 2016 after winning RuPaul’s Drag Race. More recently, Bob won a 2022 Peabody Award for the HBO docu-series We’re Here, where drag queens travel to conservative, rural areas to support local LGBTQ+ communities. In 2023, she dropped her comedy special Woke Man in a Dress and her debut EP, Gay Barz. Whether roasting audience members during a stand-up set or rhyming over a beat, Bob seems to have a bottomless Mary Poppins bag of punchlines.

Hot off emceeing Madonna’s career-spanning Celebration Tour earlier this year, Bob touches down in San Francisco on Sept. 19 for her This Is Wild! comedy tour stop at the Warfield. I chatted with Bob about the changing landscape for queer entertainers, her many, many creative pursuits and what queer rappers we should all be adding to our playlists.

This conversation has been edited for length and clarity.

Nastia Voynovskaya: I wanted to start off by talking about one of the biggest highlights of your year, which of course was the tour with Madonna. You had a huge task of being a hype person for someone who needs no introduction. How did you approach that role?

Bob the Drag Queen: Well, I have a lot of reverence for what she’s done for women and for the queer community and for outsiders who became insiders somehow just by being themselves. So it’s pretty easy to give reverence to someone like Madonna. I didn’t have to work too hard to find something to be reverent about.

I saw your TikTok about how Madonna’s a 65-year-old boomer at the end of the day, which I thought was hilarious. But on a serious note, what did you learn about her on the road that inspired you and how you’re going to approach your craft going forward?

Well, Madonna is the hardest worker I know. I’ve never met anyone in my life and every job I’ve ever worked — this goes from real estate to children’s theater to television to film to drag. But I don’t know that I want to work as hard as Madonna does. I mean, I’m a hard worker, but I’m not trying to compete with Madonna in terms of work-life balance, you know?

What was it like coming back from the tour? People were probably knocking on your door a lot more.

When I came off the tour, to be honest, my life was just kind of going crazy. My mother passed away right after I got off tour. And then I went to go film [the reality competition] The Traitors. Then I went on my own solo tour. So, you know, just outside of the tour itself, my life just kind of got really crazy right when the tour ended.

I’m really sorry for your loss. It must have been hard balancing those huge highs and lows at the same time.

Yeah, it was a challenge for sure.

The crowd work you do in your stand-up is so next level. How did you develop that? Do you roast your friends constantly?

My friends are always razzing each other. I also worked for years as an improv actor at this restaurant called the Jekyll & Hyde Club in New York City. I would do these shifts where the whole thing was just me doing improv, acting for eight hours and trying to make people laugh. So I think that’s actually where I got a lot of my quick wit from.

I also love your generational humor, as a millennial myself. What do you think makes today’s generational clashes or debates such a fruitful subject for comedy?

Well, I think it’s the notion that we’re not all in this together, even though we really know we all are. Like you make fun of our side parts and our skinny jeans, and we make fun of — you ever notice how Gen Z are always fake drinking stuff on TikTok? They’ll put a cup to their mouth before they start talking, but there’s nothing in the cup.

True, true. What generational differences have you seen between how millennials and Gen Z approach drag?

I think that millennials are often influenced by the divas or the over-the-top. Where a millennial might be more inspired by Whitney Houston, Dolly Parton or Beyoncé, I feel like a Gen Z might be inspired by Sabrina Carpenter or SZA or, you know, someone else very young whose aesthetic isn’t so over-the-top and wild. Millennial queens are often quite camp — big, bright colors, huge hair.

The lane for a queer stand-up comics has expanded significantly since you started. What are your thoughts on how the industry has changed? And how does it still need to grow?

I think it’s great — shout-out to people like Pink Foxx, Matteo Lane, Nick Smith, all these comedians who use their queerness as part of their humor. They didn’t have to come out — they were already out when they started their careers. And to the people who, like the Gen Xers, who had to come out — that was a different time. That’s not to begrudge them. It was about safety for them and about their ability to provide for themselves and their families and create a career for themselves. But I love that the queer landscape is changing and forms of stand-up comedy, it really is awesome.

There’s a stereotype among some mainstream, straight comedians that queer and trans people can’t take a joke, or that queer comedy is overly politically correct, which is not the case with your work. But what do you make of that debate, and what do you think it says about this moment in the field of comedy?

Well, some people don’t like to joke about things, and that’s okay. Some people do like to joke about things, and that’s also okay. And I think that a lot of straight people in the comedy world — not all — have this notion that we can’t say anything anymore. And it’s like, you can, but you’re going to have consequences. Like, you can literally say anything you want to say. And then we get to say anything we want to say in response to it.

You’re also a rapper with some serious bars. What do you enjoy about music as an outlet that you don’t necessarily get out of your other creative pursuits?

So when I was younger, I used to rap in the school’s courtyard during lunch. We’d have these rap battles and I was always really good at them. They were just so much fun. I am a musical theater person, but I can’t sing. So this is the way that I dabble with music. I love the poetry of it more than anything. The cleverness of writing outside of prose for me is really exciting.

Are there any queer rappers that you’re into right now?

Yeah, I’m a big fan of Ocean Kelly. I really love Kamera Tyme and Kandie. There’s so many. I love Doechii, Alex Miller, Mikey Angelo. I could be here all day naming queer rappers that I love.

We’re also seeing queer pop artists take over, like Chappell Roan. Ten years ago queer artists were relegated to playing a circuit of queer venues and pride events. And that’s just not the case anymore. What do you think has changed in culture that has allowed queer artists to take up these huge platforms where they’re entertaining everybody?

I’m not a historian of any kind, so please take this with a grain of salt. But somewhere between RuPaul’s Drag Race, Lil Nas X coming out of the closet, Pose and Legendary all kind of having mainstream success … Lil Nas X’s “Old Town Road” was massive. It’s the longest running Billboard No. 1 in the history of music. So to have someone like that come out of the closet says a lot. He was really happy to lean into queer aesthetics and queer vibes.

And then some people forget that some artists are queer, like Madonna, Lady Gaga and Frank Ocean. And now having someone like Chappell Roan come out, not only is she queer, she’s so camp. I don’t know the last time we had a lesbian singer who was this camp.

Yeah, maybe not ever. It also kind of goes to show the influence of drag. I mean, Sasha Colby just called Chappell her daughter.

Yeah, I love that.

You’re on the upcoming season of reality show The Traitors, and you’ve also done scripted television and theater. Is more acting on your vision board?

Acting was really my first love, but I have evolved into more of a stand-up comedian. And my name is Bob the Drag Queen, so I think a lot of people have a hard time seeing me outside of drag. And I like acting in drag, but that’s not how I trained my acting chops. Bob the Drag Queen isn’t a persona. When I’m Bob the Drag Queen, I’m not acting and I don’t change my voice. I don’t have a weird backstory for Bob. I’m really just being myself, just in a different set of clothes. So I would love to be able to do some more acting, but I think it’s going to take a special kind of director or producer who actually can see that my talents lie within my drag. I just happen to really love dressing up.

Can you give any hints of what people can expect when they come see you at the Warfield in San Francisco this week?

This is true, strict stand up. I have been doing stand up comedy for 16 years now. So, you know, it is a drag show because I’m doing it. But it’s not [RuPaul’s Drag Race] Werq the World. This is not Drag Race Lip Sync Extravaganza. This is a tried and true stand-up comedian artfully doing their craft.