Bob the Drag Queen On Winning RuPaul’s Drag Race, Self-Confidence, and Leading ‘Purse First’

Bob the Drag Queen walked onto to the dais at Stage 48 last night in a floor-length brown sequined dress. Violet Chachki, last year’s winner, pinned a crown to her wig, as he learned along with the rest of America that he’d won season eight of RuPaul’s Drag Race. Tears streamed down his cheeks as he thanked his friends and family, and reminded everyone to buy his new single on iTunes, “Purse First.” When Vulture spoke with Bob, whose given name is Christopher Caldwell, the morning after, he talked about why he knew he would win the competition, the origins of his phrase, “purse first,” and the political statement of drag.

You seemed really emotional onstage. How did it feel to win?
I pretty much immediately started crying as soon as I found out. It was emotional. It’s a combination of feelings all culminating into this one moment: There’s happiness, there’s joy, there’s intimidation. Then you’re also there with your friends who you’ve been with on this journey the entire way. There’s just so much going on in that moment, it’s hard to articulate all of the emotions.

I know they shoot each person winning. Is that a surreal moment?
It’s kind of another acting challenge on the show, but this one really counts, you know what I mean?

How did you come up with your name?
This is really interesting. Most drag queens don’t have an interesting story about how they got their drag name. The true story is my old drag name, no one could remember it, and everyone always says the wrong thing. It got kind of irritating. So I made my name as simple as possible, and I also thought it was really funny. And that’s how I ended up with the name Bob, Bob the Drag Queen. It is a little irreverent, and pokes fun while being original.

What was your old drag name?
Kittenwithawhip. [I had to explain] my name for three years, and I was like, I’ve had enough of this. I’m just going to become Bob the Drag Queen. When I changed my name to Bob the Drag Queen, everything changed for me. All of the sudden, it clicked. You don’t have to say it 19 times. Just say I’m Bob.

You said that you watched every episode. Were you influenced by the show itself?
The show inspired me to do drag. I didn’t do drag before RuPaul’s Drag Race. I moved to New York City to be a comedian and an actor, and one day I was flipping through Tivo and I saw RuPaul had a new show. I watched the first episode, and I started Tivoing every episode — this was back when Tivo was a thing. I became obsessed. I ordered a makeup kit off of Ben, TK-7 makeup kit, which is their darkest makeup kit, and I started doing drag from there.

Would you consider RuPaul your drag mother?
I don’t really have a drag mom, but whenever I write on social media about RuPaul, I always call him Dad. If there’s a picture of RuPaul wearing a bikini, I’m like, Dad, put some clothes on!

What was it like watching yourself on the show?
It felt right. This is where I saw myself being. In my mind, it was weird when I wasn’t doing it, like, why wasn’t I here before?

Were there any moments you regretted?
The only one was my leggings on the last episode. I wish I hadn’t worn leggings on the last episode. I did! Too late now.

There was a surprising amount of animosity, even at last night’s live finale, toward contestant Derrick Barry. Where do you think that comes from?
You know, people don’t know better. That’s one of the places it comes from. That people literally just don’t know better. It boils down to an old thing that originated in 1995, and the best way I can put it is this: Haters gonna hate. People who are haters who like to be mean to people, they don’t have any other choice. If that is your personality, that’s what you’re going to do. And there’s nothing me or RuPaul or anyone can do to make you not be a hater. People are mad at Derrick because of a couple of arguments on the show, but the people he argued with, we’re not mad at Derrick. We have come full circle with Derrick. If you are a hater, you have to take a step back look in the mirror and go, Well, I’m a hater. Can I accept that as my new personality? It kind of grosses me out to be honest, but I’ve grown to expect it from people.

Can you tell me about the origins of “purse first” (Bob’s phrase for when he walks into a room with his arm extended and purse sticking out)?
You see the entire life of purse first. It started on the show. I came up with it on the spur of the moment, because I had extra time after I made my dress and I made the purse. And then, the rest is history. I started really liking the purse. I carried it around everywhere I went on set, and then other girls started liking the purse and using the purse and it became a whole thing.

It feels like it became a metaphor.
You know, it’s really funny, my mom used to always say, Put first things first. So maybe it came from that subconsciously, but as I started doing it, it became a mantra to me.

You have a chest tattoo. What does it say?
My chest tattoo says, “I get up out of bed, I put on some clothes, ‘Cause I got bills to pay.” Which is my mom’s favorite song when I was younger, it’s called “Deeper Love.” It’s a mantra that says no matter what you do, you put first things first, basically. No matter if you’re tired or your anxious or you’re excited, or what, what you gotta do, is you get up and you go to work. You’ve got to work it.

What are you hoping to do with the $100,000?
I’m hoping to invest in my drag and to continue my mission. My mission is three things: Give back to the community, entertain the children, and make people laugh. I’m hoping to use that money to continue my mission.

You were the most politically activated of the contestants. Were there other political issues that are important to you or that you think are important to the queer community in general?
I just started a fundraising initiative called Charity for the People. My four areas that I work on are queer youth, elderly queer, HIV/AIDS and cancer, and battered women in women’s shelters. I’ll auction off memorabilia from the show. I’ll do certain shows and I’ll donate money to different causes. If I’m doing a show in Atlanta, then I’ll pick a charity in Atlanta.

Do you see drag as a political art form?
Well, drag is political in and of itself. Drag can’t be apolitical, just because it is a slap in the face of heteronormative behavior and not only that, but a smack in the face. It is counterculture. Drag is counterculture. Counterculture is in itself activism.

What does drag mean for you, especially when you started doing it?
For me, drag is the ultimate art form: You don’t need to get on a soapbox, because you’re already standing in high heels. Having people’s attention is having power. It’s the same thing. If you have everyone’s attention, then you have power. The question then becomes, “What are you going to do with this power? What are you going to do with this attention? What are you going to do now that people are looking at you?”

What are your inspirations for creating your character? Drag is so much about pulling from other cultural references.
It’s really funny. I don’t say that I have a character, because I am the same in and out of drag. I just happen to be wearing an outfit and a wig one way. I am loud, I am political, I am social. I am a butterfly. I am an artist in and out of drag. I had a lot of these traits before I started doing drag, drag just really helped me unlock my ferocity. Drag is magical and carries power. 

What was it like to lip sync for your life against Derrick?
When I got that phone call, I knew where I was going to end up. Even lip syncing against Derrick, was I a little nervous? Yeah. But I had the mindset that I was going to pull through and still end up America’s next drag superstar. Going home was never a thing in my head. I never envisioned myself going home, and I never envisioned myself not winning.

I love that confidence.
Well, thank you. After my performance last night, I said that a lot of people really come down on me for believing in myself, which is such an odd thing. I came from a generation where self-confidence was the word. It was all about believing in myself, and I spent a lot of time as a young person not believing in myself, and not thinking I was worthy of praise and adoration and good things. I just found out how to love small things about myself and celebrate that, instead of harping on what I didn’t like. And that kind of confidence can bother people because not everyone has that. Of course I have insecurities. Everyone has insecurities. But I’m choosing not to focus on that. And everyone thinks that somehow equates to me being arrogant. There’s nothing wrong with knowing what you’re good at and embracing that.

It’s surprising how people have said that. To me that’s why you won, because that self-belief is what you need to be the next drag superstar.
I’ve never considered myself arrogant. I’ve always just considered myself confident, but this was the first time when I’ve ever been anywhere where across the board, they’re like, you are so arrogant. Oh okay, I guess. I don’t know what to say to that.

Where do you see drag go next?
It’s so funny, people ask, what’s the next thing for drag? We’re at the dawning of the new age of drag. We’re still in this era. Drag is mainstream, and it’s not mainstream. Drag is smart. Drag is subversive. Drag is scary. Drag is comforting. Drag is assuring. Drag is accepting of anyone that wants to do it. Everyone’s like, What’s the next thing? Drag is perfect. I don’t want to see drag change. The thing is, drag is constantly changing, while maintaining its integrity as one of the most pure art forms I believe there is.

Talking With Bob, RuPaul’s Drag Race S8 Winner