Bob the Drag Queen wears many hats, both literally and figuratively. As an actor, novelist, podcaster, drag queen, reality TV competitor, and comedian, he refuses to be defined by a single role. And whether he’s wearing a dramatically wide-brimmed electric-blue hat on the reality show The Traitors or a backward baseball cap while playing horror video games for his YouTube channel, he brings his authentic self.
Best known as a drag performer, Bob the Drag Queen cut his teeth in comedy. (Photo by Albert Sanchez and Pedro Zalba)
Bob’s real name is Caldwell, though these days he goes by Bob. He grew up in Georgia, Alabama, and Mississippi and considers Atlanta his hometown. He was raised by a single mother with one older brother.
“I loved to laugh,” says Bob. “I loved to make people laugh, singing and dancing. I had a mom who really believed in me. We were not wealthy, and I knew it, but I didn’t care.”
He was influenced by the comedy of Wanda Sykes and remembers endlessly rewatching comedy specials like Chris Rock’s Never Scared on DVD. Bob moved to New York in 2008 at 22 to pursue theater, and for many years he found it to be an “unrequited love.”
But his relationship with comedy was less fraught. “Stand-up comedy was my first mutual love,” Bob says. “I was seeing success in that much faster than I was seeing it in theater and acting. It took me about 17 years to get on Broadway, and it took me about three weeks to get onto a stand-up comedy stage.”
He performed in his first comedy show in the late aughts at the New York Comedy Club. Although he didn’t have mentors in that world, he learned comedic timing from queens like Bianca Del Rio.
“They didn’t know they were my drag moms,” he says, “but I would go to their shows and take notes.”
Despite working as a comedian for decades, Bob says many people don’t know he does comedy. In 2016, he was winner of RuPaul’s Drag Race Season 8. The title propelled him to fame.
For Bob, his drag, like his comedy, is built not on a persona but on his experience.
“People have a hard time realizing that I’m being myself — I’m just wearing different clothes,” Bob says. “When I started doing drag, I built a persona, but I was only able to keep up with it for like two weeks. It was too exhausting living in this character nonstop.”
Onstage, Bob often wears elaborate hats or updos paired with dresses ranging from the elegant to the avant-garde. In his recent comedy special This Is Wild, he wore an ombre multicolored gown and turban overlaid with sequined black animal prints designed by Joshuan Aponte. Underneath it all, Bob performed with his usual commanding stage presence — outspoken, with plenty of opinions to dish out on Shrek, Tyra Banks, and the Sims.
Earlier this year, Bob returned to his first love: acting. He made his Broadway debut as Harold Zidler in Moulin Rouge! The Musical in January and in November is set to star as King Herod in West End’s Jesus Christ Superstar, one of his dream roles. He was offered the role without auditioning.
Bob the Drag Queen will perform at Provincetown Town Hall on Aug. 22. (Photo by Albert Sanchez and Pedro Zalba)
“It’s kind of crazy that I get to actually be in this show,” Bob says. “But I also think that my desire to be onstage and my inability to get cast in things has kind of forced me into not seeing myself onstage anymore, which is why I’m writing roles for myself instead.”
Bob is working on a stage adaptation of his recent New York Times best-selling book Harriet Tubman: Live in Concert, which he also plans to star in. In the novel, Harriet Tubman comes back from the dead to write a hip-hop album and a show that documents her life.
Bob has also starred in several TV shows including A Black Lady Sketch Show, and he earned a Peabody award for the HBO docuseries We’re Here.
When Bob isn’t onstage himself, he enjoys serving as a mentor to other comedians and drag queens. He’s built close relationships with people he’s worked with, including Monét X Change, who co-hosts the podcast Sibling Rivalry with Bob.
His mentorship skills are perhaps a trait left over from his teaching days. He studied theater education at Columbus State University but dropped out after three years and moved to New York. For a time, he also worked in children’s theater at Climb Theatre in Minnesota.
“I actually thought that was going to be my career for a long time,” he says, “and then I started telling dirty jokes.”
Bob still loves teaching. “I love to be able to cultivate people’s talent and help them get onstage,” he says. “I know how much theater and performance has done for me, and I love to be able to see that genesis in someone else.”
For the future drag queens, Bob has a message.
“Years ago, a drag queen named Hedda Lettuce told me, ‘You want to be legendary in drag, you don’t got to be good. You don’t got to be decent. All you got to do is just stick around and refuse to leave, and you will become a legend.’ ”
A Life in Character
The event: Bob the Drag Queen Live
The time: Saturday, Aug. 22, 7 p.m.
The place: Provincetown Town Hall, 260 Commercial St.
The cost: $45.75-$94.50 at payomet.org