Bob the Drag Queen Takes Us Inside Madonna’s Celebration Tour

Bob the Drag Queen, photographed by Ricardo Gomes, on Madonna’s ‘Celebration Tour’.

Few are the pop stars who could render the illustrious Bob the Drag Queen an opening act. Bob, the podcaster, television host, actor, activist, and season eight winner of Rupaul’s Drag Race, is used to headlining gigs—and for good reason. But that was before Madonna asked her to be the hype man and opener on her career-spanning Celebration Tour, which kicked off its U.S. leg at Barclays Center on Wednesday night. Before the show, our Editor-in-Chief and Madonna megafan Mel Ottenberg called Bob to find out about the gig of a lifetime.

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MEL OTTENBERG: Bob, listen. I’m flying blind because I’m seeing the show tonight and I didn’t want to watch clips on Instagram beforehand. So what do you have in store for me? Are you a long-time Madonna fan?

BOB THE DRAG QUEEN: I started being a fan of Madonna around the song “Don’t Tell Me.” And then I really got into Madonna after seeing her at the Barclays Center, so it’s funny that I’m going to be performing with her tonight where I first saw her, at Barclays, on the Rebel Heart Tour. I mean, first of all, you’re going to be getting more decades, some songs Madonna hasn’t done in a concert in years, some songs she’s literally never done in concert, which is really exciting. 

OTTENBERG: What is it like being on tour? A big Madonna tour?

BOB: You know, it really doesn’t feel much different than being on the Werq the World Tour, the other tour that I’ve done. It’s just scaled up. But also there’s so much of it that I don’t see. We have 16 buses. It’s so vast you don’t even see all of it.

OTTENBERG: What’s the best thing about being on the road?

BOB: Well, the truth is–this is why I’m so bad at interviews, because I’m always so honest. I feel like I should lie more. I don’t love traveling. I hate it. I wish that I could find a way to make people come to me as opposed to going to people to perform. But being on tour kind of feels like you’re at summer camp, because you’re seeing the same people day in and day out, and you end up building these really close bonds. Then, at the end of it, they move back to Australia and Italy and Minnesota and Florida.

OTTENBERG: The rumor is that everyone on this tour is cool though.

BOB: Yea, everyone’s cool.

OTTENBERG: How do you deal with being the hype man on days where you just don’t feel it?

BOB: It is very rare that I don’t feel like getting up and performing. And I mean, incredibly rare. There are times where I’m like “Ugh, the world feels bleak, I can’t perform now.” But for the most part, I’m almost always happy to get on stage and perform. I can remember years ago, my mom got shot and I had to perform that same night. That was pretty tough. She’s alive, by the way. Don’t worry. But I was like, “Oh my god, I have to perform. This feels dystopian.” But I also get a chance to go on stage and help people feel good for a moment, too.

OTTENBERG: I’m glad your mother’s okay.

BOB: It was years ago. She’s great.

OTTENBERG: What’s your favorite Madonna era? And you can’t say now.

BOB: I can say whatever I want, for starters.

OTTENBERG: Yes, you can.

BOB: I was really into MDNA Madonna. I was really into her two songs she did with Nicki [Minaj]. Shoutout to Nicki for Pink Friday 2. And that was just a really fun era for me, my New York City nightlife heyday. When I was really in these New York City streets, running around, performing, living my little dreams.

OTTENBERG: Do you have a favorite Madonna boyfriend?

BOB: Maybe, but not really. Some of them really intrigue me. Like, what’s up with her and Tupac? That’s really interesting to me.

OTTENBERG: It is.

BOB: The thing about me is, I’m not particularly compelled by romance. I hate when we have to pause a movie to engage with the love interest. I’m always like “Ugh, I don’t want to hear from this fucking love interest. I want the action of the movie to start again.” But there are particular moments in Madonna’s life that I find really compelling.

OTTENBERG: What comes to mind?

BOB: I’m really intrigued by her in the ’80s, passing out her CDs or tapes, going to clubs, performing at CBGB’s, performing at Paradise Garage while her friends held flashlights because there were no spotlights there. I’m intrigued by Madonna working at Dunkin’ Donuts and getting fired for having an attitude problem. I’m intrigued by Madonna working at the Russian Tea Room and getting fired because she wanted to wear fishnets.

OTTENBERG: She always has that same spirit. They needed something to listen to in the club scene in Desperately Seeking Susan, and she’s like, “Oh, play this demo tape. It’s not finished, it’s just the tape.” And then they put it in and everyone dances to it for the whole scene. And that’s “Into the Groove.” Magic! I highly recommend the Mary Gabriel biography that just came out. The ’80s part, you just can’t stop reading it. Anyway, what time are you going on tonight?

BOB: The show’s around 8:30. And we have a DJ beforehand.

OTTENBERG: I’m excited to see this show and I think you’re fucking awesome.

BOB: Oh, thank you.