In Bob We Trust: New York’s Newest Reigning Drag Queen Snatches America’s Wig

In Bob We Trust: New York’s Newest Reigning Drag Queen Snatches America’s Wig
Photography by ioulex

His majesty, Bob The Drag Queen, has requested an audience at the 110th Street Chipotle, and nowhere else will do. The people who represent Bob had explained to me that Bob wanted to meet "somewhere near Bob" — a riddle, surely, as at any given moment the recently crowned winner of the reality TV cult hit RuPaul's Drag Race could be just about anywhere in the country. The week before, his coronation tour had stopped in San Jose; by week's end he'd be in Sacramento, and then it's on to Boston, Washington, Chicago, Denver, Portland, and Pensacola before headlining the Pride Rally in New York on June 24.

But on this sunny Tuesday afternoon in late May, Bob happens to be home, on the Upper West Side, and at exactly 1:15 p.m. he arrives at Chipotle fresh — fresh-ish — from a slumber party with Drag Race judge Michelle Visage and RuPaul himself. Tall and bald, wearing track pants and a tank top, Bob more or less blends in with the crowd of bleary-eyed Columbia students hanging around. And then he walks up to the counter to order: He'll have a chicken burrito. With vinaigrette on top. The line cook looks at him hesitantly. Bob doesn't blink. His septum ring sways hypnotically. The line cook pours vinaigrette on a burrito.

We settle into a corner high-top where Bob plans to hold court for the day — he'll be having other meetings here after this one — and I ask him who he's seeing next. "I thought this was a date?!" he laughs. "Get your hand off my leg!" From there, he launches immediately into the presidential election: "Trump is racist, and the reason why he's popular right now is because he lets a lot of people act racist without saying the word racist," Bob says, putting down his burrito. "He's a racist, and his supporters are racist, and they get to be racist without saying they're racist. I said racist, right?" He leans in to the recorder and yells, "RA-CIST." He picks his burrito back up and mutters, "Racist." He takes a bite.

"Racist."

For reasons I leave it to posterity to decipher, I decide to ask Bob what he thinks about Beyoncé. Bob says he hasn't seen Lemonade — "Under no circumstances am I going to download Tidal" — but he did see her Black Pantherish Super Bowl show. What did he think of it? Something settles; the giggling stops. "Every black person goes through a phase during which all they can think about, all they can talk about, all they can do," he says, "is being black." When I ask if that phase is over for Bob, his laugh catapults avocado at me.

"No."

In Bob We Trust: New York’s Newest Reigning Drag Queen Snatches America’s Wig
Photography by ioulex

There's no place for wallflowers on Drag Race, a reality TV Thunderdome — with nearly as many lace-fronts — in which a dozen drag queens compete in challenges that include snap dressmaking and drag-ifying characters from The Wizard of Oz, all while being judged on details as minute as the heaviness of their eyeshadow and how completely they've tucked away their penises. The personalities are huge, and Bob eclipsed them all. In his first on-screen one-on-one with RuPaul, Bob announced that his name stood for "Big Ol' Bottom" and explained his life philosophy: "There really is no reason to pretend to be modest."

It was bravado, sure, but Bob had the goods to back it up. In the fifth-episode challenge he sent his castmates into panic spirals with his exquisite, back-to-back-to-back impressions of Whoopi Goldberg's lounge singer turned nun from Sister Act, Uzo Aduba's Crazy Eyes, and Carol Channing, of Hello, Dolly! fame, in what was undoubtedly the most effective use of wigs in the history of psychological warfare. He won, though not without being reprimanded by Visage for "showboating." (Bob got his revenge during the season finale lip-sync battle, when, dressed like a backup dancer from a Nineties-era Missy Elliott video, he performed an original song titled "I Don't Like to Show Off." The joke was that Bob likes to show off.)

Even as Bob was striking fear in the hearts of his castmates, he was also emerging as the show's most politically attuned player, unafraid to delve into sticky issues like race and gender, always up for a quick civics lesson. "Politicians make very real, important decisions for you," he explained to a fellow competitor named Naomi Smalls in one episode, during a lecture on the importance of voting. "Oh, you can de-fi-nite-ly do something about it" ("it" meaning just about whatever problem might need something done about it). In one of his talking-head interviews, he proudly described the time he was arrested for obstructing traffic while marching for equality near Bryant Park: "They fucking threw my ass in jail. In full drag, girl!" Cut to a candid snapshot from the arrest, showing Bob in full makeup, a vest, tie, and a massive red Afro.

In person, he's no different. Sitting in Chipotle, Bob reads the whole of American politics like a menu: In addition to the Trump analysis, I learn that Bernie Sanders is the Naomi Smalls of the election ("You love him, but he's probably not going to win") and why people only take women seriously if they're really butch ("Can you imagine if Hillary was in a sundress? 'Hey, boo. Vote for me.' ") He dares me to name a single woman politician who dresses femininely, then immediately supplies his own answer: Stephanie Rawlings-Blake, the mayor of Baltimore, who made national headlines last year when she advocated for the prosecution of the cops in whose custody Freddie Gray was killed. He jumps into an off-the-cuff impersonation of Rawlings-Blake warning city residents to stay home during a snowstorm: "If you don't have a job, stay at home. Why y'all out on the street? Watch some Netflix and let us do our jobs.'" He pauses.

"I love her," he says. "She reminds me of my mom."

In Bob We Trust: New York’s Newest Reigning Drag Queen Snatches America’s Wig
Photography by ioulex

Bob is a Manhattan Queen. The 30-year-old moved to New York eight years ago, and it was here that he made his first attempt at drag, at Pride. ("There are two breeds of queen," Bob informed Derrick Barry, a Britney Spears impersonator, in one episode of Drag Race. "There's Halloween queens, and there's Pride queens. I was a Pride queen, wearing a fucking potato sack and a wig from who knows where.")

But before Bob was Bob, he was Christopher Caldwell, raised in Georgia by his mother, Martha Caldwell, a computer network engineer. Growing up, Bob was a theater kid, appearing in Grease, Jesus Christ Superstar, and Annie, and a step-dance star who took his high school team to nationals. He'd help his mother on various volunteer projects in their community, like at the YMCA where, on the days she was out, he taught her computer class step-dance choreography. After graduation he studied theater at Columbus State University and gradually became a working performer and comedian, booking shows on the slam poetry circuits in Atlanta and New York.

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Soon stand-up and slam gigs were taking him away from Columbus so frequently that one day a friend told him that if Bob was willing to drop out and make a real go of it in New York, he'd buy the ticket. So Bob did. He moved to the city and began gigging regularly at the New York Comedy Club and Carolines, where he noticed that club bookers paid closer attention when he was in a wig. Before long he was performing at clubs up and down Manhattan, building up a cult following thanks to the same impersonations that would eventually help him win the crown on Drag Race and becoming known for his full-throttle LGBTQ-equality activism, which included staging weekly drag queen weddings in Times Square to protest for marriage equality. Then Drag Race came along.

In a way, Bob's win was inevitable from the second RuPaul plucked his audition tape from the pile. "Every challenge they gave him, every last bit of it, he'd already done in his life," says Martha, his mother. "From making purses to making the dresses" — in fact, he used to make dresses for Bebe Zahara Benet, Drag Race's season-one winner — "to the musicals."

Bob's life experience has also informed his act, and his success, in subtler ways. Spend any time with Bob, or just watch him on the show, and you begin to realize just how much his mother has shaped who he is. "If you ask anyone which of their parents is the strongest, everyone will say their mothers," Bob says. "Most of the men in my family don't even hold a candle to the women."

His respect for black womanhood comes out in his act and is part of what makes it so good. At the very beginning of the season, he made a point of announcing his preference for unbraided or relaxed natural-hair wigs. And his impersonations avoid cartoonishness in favor of dead-on accuracy: His Crazy Eyes is successful because he fully realizes her craziness; his Annalise Keating (from How to Get Away With Murder) is as fish-eyed and paranoid as Viola Davis's rendition; his Sister Mary Clarence slaps knee as well as the real McCoy.

Bob's nuanced approach to race and gender taps into a criticism that has often been made of drag, the modern form of which emerged from the black and brown ball culture of the Seventies and Eighties: that it purloined everything — the humor, the language, the mannerisms — from black women, and sanitized it for mass consumption. That's how you get things like Tyler Perry's Madea, The Nutty Professor, and Big Momma's House — films in which caricatures of angry black women are played for laughs.

It's a charge that Drag Race itself hasn't escaped, despite the fact that its host and creator is black and that six of the eight season winners have been people of color. In one episode last season, Visage complimented one of Bob's looks for not being his typical "ratchet drag." And the show has more than once been criticized for retrograde representations of blackness, such as a challenge in the most recent season in which the contestants spoofed the Fox series Empire, which features a nearly all-black cast. RuPaul's advice to a Korean contestant named Kim Chi was to "pop her tongue" to make her character more authentic, and in Ru's own performance of Lucius, the Empire family patriarch, he demanded, "Which one of you bitches is gonna get my empire?" When it was his turn, Bob exposed the minstrel undertones of the challenge by leaning into them. During rehearsals he coyly inquired, "Which hand should I use to slap a 'ho?" In another challenge he appeared in full whiteface, declaring himself, with a straight face, "someone to finally stand up for white people."

In Bob We Trust: New York’s Newest Reigning Drag Queen Snatches America’s Wig
Photography by ioulex

Before sitting down with Bob I was firmly reminded by Bob's retinue that my time with him would be limited to thirty minutes. Thirty minutes pass, then forty-five, and Bob is still going, pondering aloud whether he should move to Canada in the event of a Trump win, talking about a Florida nonprofit for queer youth to which he donated a portion of his prize money, and explaining what's next for him. In the immediate future, there's a Drag Race reunion tour, and Pride, of course, and the documentary Bob is making about himself, funded through a Seed&Spark campaign that raised $20,000. (The working title is Bob's slogan for himself: Queen for the People.) Beyond that, who knows (well, maybe Canada).

As we wait for his next petitioner to arrive, I ask whether Bob's days as a community activist are behind him now that celebrity has arrived. He's busier now, after all, and it wouldn't be the first time someone started toning down their rhetoric once they entered the public eye. He doesn't hesitate: "I've always said that I will be where I'm needed most," he replies. "There was a time when I was needed on the front line, yelling, getting arrested. I feel like now, now I'm needed more advocating from this side of the jail cell. But if there ever comes a time where I need to be on the front line, that's where I'll be."


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