Bob the Drag Queen Loves Dressing Up and Doing Absolutely Nothing—Just Not at the Same Time

“Madonna’s her own micro economy at this point,” Caldwell Tidicue, a.k.a. Bob the Drag Queen, tells me from his Barcelona hotel room. 

The comedian, actor, singer, and all-around performer is currently on tour with the Queen of Pop. Bob initially rose to fame as the winner of Season 8 of RuPaul’s Drag Race and since then, he’s graduated from reality TV to appearances on A Black Lady Sketch Show, Single Drunk Female (R.I.P.), and The Simpsons, even hosting the HBO show We’re Here with fellow former Drag Race competitors. Now, he’s dancing with Madonna on stages across the globe, a project that has been in the works since November 2022.

“It’s been pretty exciting and fun. Certainly an eye opening experience in terms of what it means to exist in this world,” Bob says, later elaborating: “To see the amount of choreographers and designers and stagehands and stage managers who work on this project is really impressive.”

Bob has been rehearsing with Madonna and her small army of a crew since February 2023. Clearly this is a project that requires dedication, and that high level of commitment is apparent wherever and whenever you see a Bob the Drag Queen performance. He truly leaves it all on stage, a matter that’s reflected in his favorite non-work activity: doing absolutely, positively nothing.

“I really can’t emphasize how much I like doing nothing. I wish I could impress upon you how much doing nothing truly excites me,” Bob says. “I don’t mean like watching a TV series. I don’t mean like finishing up a great book. Just not doing anything is so amazing. It’s so good to do that. I truly love it.”

He explains, “I think that’s the reason why I’m so great on stage—because I save it all up. I’m not doing a lot when I’m on not stage.”

Watching Bob’s latest special, Woke Man in a Dress, you can tell that he’s putting his all into it at Madison, Wisconsin’s Comedy on State. From the moment he gets in front of the audience, blessing them with his water bottle, Bob is hyper-present. He’s in utter command of the room; with a mere hip pop or change in facial expression he has the crowd in stitches. Woke Man in a Dress was released on YouTube in September, and just last month was put out in album form so you can bring Bob’s impeccable comedy with you on the go. 

Bob channels a straight-talking, foul-mouthed teacher for the hour. He calls out specific audience members by name and elaborately explains C-sections, old school internet, and the difference between gays and lesbians on vacation. “Listen up!” he orders, and we’re only too happy to oblige. You can see the influence of his comedy idols Wanda Sykes, Whoopi Goldberg, and Carol Channing, but at the end of the day, he is undeniably himself.

This album release is the last hurrah for Woke Man in a Dress, and Bob’s already looking to what’s next.

“I’m really grateful for that special. Woke Man in a Dress is kind of a retooling of my last special with an extra 30 minutes of comedy attached to it. And I’m really proud of the success from that one. I’m working on some more stuff, so hopefully when I’m done touring with Madonna, I can go and do my own solo tour that I’ve been dying to do forever,” he says.

 Bob’s a strong believer in the idea that “you can make humor from just about anything.” He adds, “The main thing is you gotta get in front of an audience and try it out over and over again until it’s presentable.” 

For Bob, that used to mean New York clubs, but these days he’s based in Los Angeles and tends to try out material in places like West Hollywood’s The Comedy Store. 

When I ask if he’s ever worried about the fame feedback loop, where audiences love a comic so much it’s hard to tell which jokes actually work, he clarifies, “I’m not even in drag. It’s like, Oh, it’s just some guy up there telling jokes. So that’s why I feel confident to remember that I really am a funny person and I’m not a fraud. Again, I’m not out here faking it. I have put in the work. I’ve been doing comedy for about 15 years now.”

As for the drag element of his show, Bob just genuinely loves donning a dazzling outfit (and he has many). 

“For me, drag isn’t a means to an end. I’m not dressing up because I think it’s the only way people will like me. I just happen to love dressing up, and I don’t actually know any drag queens who’re doing drag as a means to an end,” Bob tells me.

“No one is doing drag cuz they feel like they have to,” he continues. “It’s not an easy occupation even to get a foothold in, let alone doing it just for the money because drag is expensive and most of us don’t make money. I make money, but most drag queens don’t… I did drag for three years in a deficit. So I think that [my comedy] is a little bit more exciting when I am in full drag. You have something more fun to look at, you know what I mean? Depending on what I’m wearing, obviously.”

Stand-ups have always dressed for the occasion when they record a special or do a show; even wearing a casual hoodie and jeans is a conscious choice, a statement about who the comic is and what their set’s going to be like.

“Joan Rivers dressed up when she did comedy,” Bob recalls. “John Mulaney wears a suit for a reason. Even Eddie Murphy, problematic as he is, was wearing those jazzy outfits. It’s pretty standard for comedians to dress up when they get on stage.”

So while not every drag queen is a comedian, all comedians have a little bit of drag in them.

Woke Man in a Dress is streaming for free on YouTube and is available in album form here.