Bob the Drag Queen on Writing His First Novel and Avoiding Karla Sofía Gascón at Madonna’s Oscar Party

Bob the Drag Queen — real name Christopher Delmar Caldwell — has blazed quite the trail for himself since winning the eighth season of RuPaul‘s Drag Race.

He’s toured with Madonna; found a legitimate place in the competitive standup scene; and even found time to appear on the American version of The Traitors — the show that stole the reality Emmy crown from Drag Race.

Now the quick-witted renaissance star, 38, is moving into higher-brow terrain with his first published novel, Harriet Tubman: Live in Concert (out today from Gallery Books).

A historical fantasy in which the slave-saving hero walks among us once more (as do other deceased celebrities) and is enlisted to record a hip-hop album, the book has earned praise from critics.

It’s just the latest feather in Bob’s multi-feathered hat. Or wig. Or purse (first). He caught up with The Hollywood Reporter for a colorful chat about writing fiction, working with Madonna and always answering the phone.

Hi, Bob. I don’t know if you remember this, but we’ve met before. You came to the Hollywood Reporter offices once with Kim Chi.

Oh my God. Wait, is this back with Billy Bush? Me, Kim Chi and Naomi Smalls put Billy Bush in drag. I think it was before the Access Hollywood scandal dropped. A few years later we were like, “Oh, look at that…”

It was after the scandal, but before Donald Trump won the first time. No one thought he’d actually win. I asked you what would you advise people if he indeed won. You had a really great answer. You said you can’t leave the country. You have to stay here and fight.

Yeah. And I’m still on that — even though I get it. If people want to leave, I get it. The desire to leave is so strong. But my ancestors literally built this country and died doing it. I’m not fucking going anywhere. I get my piece.

I think it’s important to have people like you out there fighting and representing and doing what you do.

Thank you. That’s what it’s all about. I’m just a loud mouth who can’t shut up.

It’s been a little over eight years now. How far have you come since then, in your own estimation?

Well, in the past eight years, I’ve done a lot. I filmed three seasons of my own HBO show on HBO called We’re Here, which I was lucky enough to win a Peabody and three GLAAD awards for. I have filmed two comedy specials, and I am working on my third right now. I toured with Madonna — I hosted her world tour. I filmed The Traitors.

I’ve gone through a lot as well. I lost my mom last year on Mother’s Day, if you can believe it. My nephew lives with me now. I now have a straight man living in my house. I moved to Los Angeles, California. A lot has happened. Eight years has been a lot for me.

Do you still enjoy doing drag?

I love it. The dress that I won RuPaul’s Drag Race in is displayed right behind me. Drag is one of the great passions in my life. Drag, comedy, social and civil rights are some of my greatest passions. Drag has given me a lot. Drag has gave me basically everything I have today.

You mentioned The Traitors. I did not watch your season. I did watch the second season and I think partially because of the way Peppermint was treated, I decided not to come back.

Well, that didn’t quite happen to me. I lasted a little bit longer than Pep. I didn’t go very far. I made it four episodes in, and I was a Traitor — so I was the bad guy. I’m a bit dramatic. So I really gave them a run for their money on that show.

Did you have a good time doing it?

It was a pretty tumultuous time. I had my mother’s funeral a week before I went to Traitors. It was a lot to do. If I could have done it at a different time in my life, that would’ve been fantastic. But I got it when I got it and I did it.

Let’s talk about Harriet Tubman: Live in Concert. I really enjoyed it.

Thank you. I’m getting really great reviews for my debut novel. I am not a literary scholar. I’ve always basically thought of myself a writer. I’ve been writing standup comedy for 16 years now. I thought writing a book will be easy for me. It wasn’t that easy. It took me four years to write that book.

First of all, the way it was packaged is incredibly enticing. It’s a great cover.

Those are actually Harriet Tubman’s hands. Those are her real hands holding the microphone. She wasn’t holding a microphone, obviously. She was just clasping her hands.

And then, of course, the subject is maybe surprising. This is not a sexy, campy book. This is a book about history and music.

And freedom. Freedom is a big theme in the book as well. I’ve been obsessed with Harriet Tubman and her story for years. What she achieved doesn’t even sound possible. I also love hip-hop music. So I really wanted to take two things that I love and get them together on the page and write a book. I wanted to write a book I would read.

I actually got offers where I got the book deal before I had a book idea. They came to me, “Do you want to write a memoir?” And I said, “I wouldn’t read that book.” I’ve only read a few memoirs in my life.

Did you read RuPaul’s memoir?

I read RuPaul’s first memoir, Letting It All Hang Out, which is a great book. I have a signed copy of it. Before I was ever on Drag Race, I got her to sign my book. And I read Michelle Visage’s The Diva Rules, as well. I started listening to [RuPaul’s second memoir The] House of Hidden Meanings. I’m still working on that book now.

But my life is not that interesting. I don’t drink. I don’t party. I don’t even go out to restaurants. I write jokes. I tell the jokes. I get off stage, and then I do it all over again.

Part of what’s fun about success is going around to the hotspots and getting a good table and being part of the scene. And you’re saying that that’s not really your personality?

Not really. I like going to house parties. I go to one big party a year. It’s the same party every single year.

Is it Madonna’s Oscar party?

It’s Madonna’s Oscar party. Outside of that, I might go to my friends’ game nights. I love a good game night.

Speaking of Madonna’s party, how was it this year?

I had a lot of fun at the party this year. There’s no cell phones, so there’s no pictures and stuff at the party, which I kind of like, even though I am chronically online.

I think it surprised everyone when Karla Sofía Gascón thanked Madonna for being compassionate to her and inviting her to the party. Did you meet her at the party?

I did not. I didn’t watch Emilia Pérez. And also, wasn’t she racist on Twitter?

Something like that.

She’s like a monster on Twitter, so I was like, “Maybe I won’t meet her.”

I saw a clip of your stand-up, and someone asked you what Madonna was like. You said, and I’m paraphrasing, “Sometimes it feels like you’re in the presence of the coolest person that’s ever lived. And sometimes you’re in the presence of the biggest boomer you’ve ever met.”

Like a mother of six. Like, “Oh my God, I’m with the Queen of Pop.” And then you’re like, “I am literally talking to a mother of six.” They happen back to back.

I did see you on that tour. It was amazing. You were more than just an emcee.

I also helped create the show. She really trusted me a lot. Madonna said when she sees me, she doesn’t “see ‘a drag queen from Drag Race.’” She really sees me as an artist, as a creative, as someone she really trusts to help her create her 40-year retrospective.

How did she discover you?

Her daughter [Lola] is a fan of Drag Race. For years, Lola’s Instagram picture was Michelle Visage. I think that her daughter put me on, and put her onto me. And then Madonna went down a rabbit hole watching all my YouTube videos.. And she was like, “Oh my God — this person seems so funny and so clever, so creative.”

And then one day, she just gave me a call out of the blue. I picked it up, and it was Madonna on the other side. That’s also how I got on We’re Here. I got a cold call from the creators of We’re Here. I always answer my phone. Because I’m really comfortable hanging up on people. If I don’t want to talk to you, I will hang up on you. Like, goodbye! Click.

Is that good career advice would you say? “Always answer your phone.”

I always answer the phone. But if you have too much anxiety, I am not here to tell you what you do with your life. I always answer the phone. But I have no qualms about hanging up on someone at all.