Metro Weekly

Bob The Drag Queen: I knew I would win Drag Race

The season eight champion, Bob the Drag Queen, owes his career to RuPaul's Drag Race

Bob the Drag Queen -- Photo:  MoDd
Bob the Drag Queen — Photo: MoDd

“I watched RuPaul’s Drag Race Season 1 and thought, ‘Man, that looks like a lot of fun. I think I could be good at that.’ So I gave it a shot.”

That Christopher Caldwell hadn’t tried drag before Drag Race is surprising — not least because his mother owned a drag bar in Georgia. “I did cross-dressing in high school,” he says, “but I would barely consider that drag.”

It wasn’t until several years into an acting and standup comedy career in New York that Caldwell started performing in drag, initially as Kittin Whitawhip, a play on the 1964 film starring Ann-Margret. But it was Bob The Drag Queen that would enter the eighth season of Drag Race — and ultimately bring the 30-year-old his crown and the title of “America’s Next Drag Superstar.”

“The show has changed my life more than I could even quantify with words,” he says. “I don’t personally have the vernacular to do justice to what it means to even be on RuPaul’s Drag Race, let alone win it.

“Winning was a culmination of everything I’ve done up until that point,” he continues. “I always thought I was going to win even before I made it to the studio.”

Bob the Drag Queen
Bob the Drag Queen

Two months after appearing on the Capital Pride Mainstage and at Town Danceboutique, Caldwell returns to the area as part of a tour with four other finalists from Drag Race‘s eighth season: Kim Chi, Naomi Small, Thorgy Thor and Chi Chi DeVayne. The show is hosted by Katya, the breakout star of Season 7, who will appear in RuPaul’s All Stars Drag Race Season 2.

“I don’t know what they’re gonna do,” Bob The Drag Queen says about the other queens, “but I am going to be hilarious.” — Doug Rule

Season 8: The Queens Live Across America is Monday, Aug. 15, at 8 p.m., at the Fillmore Silver Spring, 8656 Colesville Road in Silver Spring. Tickets are $37, or $77 to $252 for VIP/Ultimate Fan options. Call 301-960-9999 or visit Also Tuesday, Aug. 16, at 8 p.m., at the Hippodrome Theatre, 12 North Eutaw St. in Baltimore. Tickets are $69 to $72. Call 800-982-2787 or visit

Leave a Comment:

Support Metro Weekly’s Journalism

These are challenging times for news organizations. And yet it’s crucial we stay active and provide vital resources and information to both our local readers and the world. So won’t you please take a moment and consider supporting Metro Weekly with a membership? For as little as $5 a month, you can help ensure Metro Weekly magazine and remain free, viable resources as we provide the best, most diverse, culturally-resonant LGBTQ coverage in both the D.C. region and around the world. Memberships come with exclusive perks and discounts, your own personal digital delivery of each week’s magazine (and an archive), access to our Member's Lounge when it launches this fall, and exclusive members-only items like Metro Weekly Membership Mugs and Tote Bags! Check out all our membership levels here and please join us today!