Bob the Drag Queen has been “purse first” his entire life.
The 29-year-old drag performer, real name Christopher Caldwell, was crowned the winner of Season Eight of RuPaul’s Drag Race Monday night, the same day that the music video for his new single, “Purse First,” debuted on YouTube.
It’s an homage to the catch phrase the season-long frontrunner coined on the popular Logo reality competition. In the first episode, he made his outfit so quickly that he used his extra time to make a purse and decided to showcase it on his runway walk, strutting purse first. But it’s also, it turns out, a bit of a lifelong obsession.
“When I was younger I used to make wallets and purses out of newspaper and I would give them out to people,” Caldwell says, speaking to The Daily Beast the morning after winning $100,000 and the title of America’s next drag superstar. He laughs: “My whole life I’ve been purse first.”
As any Drag Race-obsessed fan will tell you—and with Drag Race, there is no other kind of fan—Bob the Drag Queen’s eventual victory was foretold from the first day of competition, where he emerged early and clearly as the frontrunner and never faltered. Even at New York City’s finale party, where the winner was crowned and the top six Season Eight queens performed, Caldwell’s competition admitted that even they knew it was always going to Bob.
“We were backstage being like, ‘Bitch, we already know what’s going to happen,’” Naomi Smalls, one of the two runner-ups, joked to the crowd. “We all knew Bob was gonna win,” Kim Chi, the other runner-up, said.
The fact of the matter is that even Bob the Drag Queen knew that Bob the Drag Queen was going to win. “When I got the phone call that I was going to be on Drag Race I thought I was going to win,” he says. “I thought I was going to win Drag Race before I was even cast.” After I laugh, he interrupts: “I’m not even being funny. I’m being serious.”
That confidence was both the greatest asset and, at least according to the judges, the only weakness of Caldwell’s, with judge Michelle Visage warning him against “showboating” during one challenge where his level of performance was stilettos above the competition.
“That was interesting because on Drag Race they ask you to bring your best drag. They always say it’s ‘the Olympics of drag, bring your A-game every time,’ and then I brought my A-game and they were like, ‘This is too much,’” Caldwell says.
And Caldwell knows his Drag Race history. He’s watched every single episode, and has said that watching the first season is part of what inspired him to start doing drag.
Now that he’s the Season Eight winner—in addition to the prize money, an AXE “Find Your Magic” commercial that celebrates all different kinds of masculinity will feature his winning moment—we chatted with Bob the Drag Queen about his victory, where he gets his confidence, his first experiences doing drag, and what it’s like to have even RuPaul himself going “purse first.”
What was that coronation moment like last night?
It felt right to me. It didn’t feel odd. It didn’t feel out of place, because that was my goal coming in. From the moment I walked in, my goal was to win. So it didn’t feel foreign.
I love that you said it felt right. So many people feign humility when this happens. But the whole narrative of the season was that you deserved this. It must be an interesting moment, to have a moment that you felt like you deserved.
I am quite humbled by this process. But I don’t understand this whole concept of you having to act like you don’t deserve things to deserve things. You can also be proud of yourself and be humble. I don’t know where this concept came from where you have to act like you don’t deserve nice things. It’s odd to me and it’s something that I never subscribed to. I feel like you have to believe in yourself and treat yourself like a winner. If you’re not going to treat yourself like a winner, how do you expect anyone else to? If you act like you don’t deserve nice things, they’re going to treat you like you don’t deserve nice things. You know what I mean?
What it did feel like in the mix, competing on the show, when everyone thought you were going to win?
It’s a lot of things. It feels interesting because a lot of people attack you for that. I got a lot of backlash for believing in myself, which is interesting because I grew up in the generation that was all about self-esteem and believing in yourself. If you’re 28 to 33, self-esteem was the word of the week every week growing up. Self-esteem and arrogance are not the same thing. I know a lot of people read it as arrogance. But I never did anything that I thought was rude or arrogant, per se. I just believed in myself, which seemed to really bother people. It really irked people.
On the idea of confidence vs. arrogance, the critique that kept being replayed this season was when Michelle Visage clocked you for showboating.
That was interesting because on Drag Race they ask you to bring your best drag. They always say it’s “the Olympics of drag, bring you’re A-game every time,” and then I brought my A-game and they were “this is too much.” Michelle was like, “This is way too much.” So I just said I was going to do what I came there to do, which is my best.
Did you think you were going to win, the way that everyone else assumed you were going to?
I’m not kidding around: When I got the phone call that I was going to be on Drag Race I thought I was going to win. I thought I was going to win Drag Race before I was even cast. I’m not even being funny. I’m being serious. Before I was even cast on Drag Race I was like I’m going to win Drag Race. I remember watching Bianca Del Rio win Drag Race and thinking, “That is going to me.”
People have called this one of the strongest seasons ever, with the best Top Three. As a student of the show, do you agree with that?
It’s hard to step back. I’m too close to it. I’m in it, you know what I mean? But if I was watching the show I think I would have been going crazy screaming the whole time. I really do. If I wasn’t on it and was watching it, I think I would love it.
What did it mean to have RuPaul go purse first at the finale?
That was crazy! What they didn’t show is that he actually got up and walked off the stage purse first. I literally just stood there pointing with my mouth open. It was all I could do.
What did it feel like to have Ru, of all people, paying homage to your signature?
Considering how many times I’ve yelled “sissy that walk” and “you better werk,” it’s surreal. That is not something that I envisioned coming in, that RuPaul would be quoting me and having fun with that.
Well, every girl last night was walking around purse first at the finale.
Isn’t that crazy?
That you, a student of the show, are now the winner signals a new wave in the drag movement. What is the impact of Drag Race on the next generation of drag?
We’re in the drag queen renaissance right now. The past two rebirths of drag have both been at the hands of RuPaul: when she released “Supermodel” and when she launched RuPaul’s Drag Race. I’m part of that second generation from her. I think it will show people that you can dream things and you can achieve them. Dreams really do come true, which sounds so cheesy but it’s really true.
Do you remember the very first time you did drag?
I didn’t even perform. I bought a wig. I was at gay pride. I wanted to prance around. I was with my lesbian friends. We went to a pier dance. It was an all-lesbian party. I wore a skirt as a dress. I had the skirt pulled all up over my boobs. I had some hooker boots up to the knee and a flat wig with bangs. I got so many compliments, despite how I looked. It was a really amazing thing, even though my feet hurt so bad I couldn’t walk. I was literally on my hands and knees crawling at the end of the night to get home. But I remember that it felt magical. Maybe this is how some of the greats felt when they realized what they’re good for. When Beethoven discovered the piano or when Picasso discovered the paintbrush. When I did drag, I felt like oh wow, this is my thing. This is what I’m supposed to be good at.
What about the first time that you performed in drag? Do you remember what that was like?
I do. I started doing drag as stand-up comedy. I didn’t even start lipsynching until a couple of months into my drag. Actually my first drag performance is on the Internet under the title “Funny Drag Queen Part One.” I did a stand-up comedy set. All my friends at the restaurant I worked at came out to see me. It was probably one of the most magical nights of my life.
Where does your confidence come from?
You know, it comes from learning to love small things about yourself before you can love your whole body. We all have things we don’t like about ourselves. My quote-unquote “arrogance” is just me not focusing on things I don’t like about myself. It is really funny to me that I got heat for believing in myself. That’s what you should want to do. You should want to believe in yourself. And the fact that I got chastised for believing in myself so much I think is a negative message for people who need to believe in themselves more. It comes from not focusing on what you don’t like about yourself. Focus on what you love about yourself! Then everything else will fall in place. You know that line “free your mind and the rest will follow?” Love one thing about yourself and the rest will follow.
Your brother and your mom both spoke lovingly about you on the finale. What is it like for you to hear that?
It was great to have my mother there. I wish my mom could have come but she can’t fly because of medical stuff I don’t even understand. My mom has been my biggest cheerleader since the day I was born. She means the world to me.
People tend to be surprised when a parent is supportive of their child’s drag. What has your relationship with her been like as a drag performer? How has she felt about it?
When I was young, my mom used to own a drag queen bar so it wasn’t a big stretch. I firmly believe that parenting your kids regardless of anything should be exalted. But it’s more than that. It shouldn’t be just praising someone for loving their kid. That’s the bare minimum for having a child. You should love your child. You know what I mean? That shouldn’t be the exception. That should be the standard. Everyone is shocked when someone loves their child. I don’t understand why everyone is so amazed that a mother could love her child.
Your mom owned a drag bar—this really was destiny for you.
I know, right? On a side note, my mom was telling me last night that my whole life led up to this point. When I was younger I used to make wallets and purses out of newspaper and I would give them out to people. She says the dance classes, acting classes, and stand-up comedy, the purses I used to make, creating things around the house, that it all seemed to lead up to this.
You’ve been purse first your entire life.
My whole life I’ve been purse first.