From the moment he stormed the workroom (and the worktable) Bob the Drag Queen made himself a force to be reckoned with on Season Eight of “RuPaul’s Drag Race”. With razor sharp wit and runway presence to match, Bob let us all know that you don’t need to take yourself so incredibly serious to take the crown. He walked the runway “purse first,” all the while staying true to exactly who he was. We sat down and chatted with Bob about what it’s like to be the second winner from New York City, his thoughts on some of his favorite queens, and what advice he just may give the Bob the Drag Queen that walked into the workroom on that first day.


Congratulations on bringing back the “RuPaul’s Drag Race” crown back to New York City! Was season six winner Bianca Del Rio, your fellow New York City sister, happy when you won?

Are you talking about Bianca Del Rio? NO! Actually, Bianca is a lot sweeter than you would think.


You were one of the most popular queens working in New York City and worked all over town. What made you want to try out for the show now?

You know, “RuPaul’s Drag Race” is a game changer. Right now, RuPaul has made herself the Jesus of drag; the only way to get that kind of fame through drag is actually through RuPaul. I wanted to be a part of that amazing legacy; and I am girl!


So many of us have known you and seen you live, and you were totally “Bob” from your first appearance in the workroom. At what point in the competition did you maybe say to yourself “Wow, I actually could snatch the crown?”

When they called me to be on “RuPaul’s Drag Race” I felt that way. I always say, you shouldn’t compete on “Drag Race” unless you’re competing to win.


Were there any of your competitors that you thought could really give you a true run for your money?

All of those girls were really great. Except for Naysha Lopez. (LOL). Honestly, Naysha Lopez is a former Miss Continental. That is a very big deal and something I could never do. We’re all great at something. You have everything from classically trained violinists to standup comedians to brilliant makeup artists, and that’s just Season Eight!


Now that the season is finished and you have a full year ahead of you as “America’s Next Drag Superstar,” what do you think your favorite part of the whole experience was?

You know, the first episode was so much fun and it was such a great experience. Filming the first episode is like the first day of school and filming the last episode is like the last day of school, and filming the reunion is like our high school reunion. It’s jammed into one year as opposed to over twelve years. I’m really proud of my graduating class.


Does winning and actually having the crown really feel the way you thought it would?

The short answer is no. I was very popular in New York City. I have a plaque that says I am the “Undisputed Queen of New York City” and that was before I was on “RuPaul’s Drag Race.” After being on “Drag Race,” I knew that there would be haters though. I kind of like haters though, I mean, I would never stop them from hating, because you know, haters are gonna hate. I would never take away the one thing that makes them happy, I mean who am I to take away their joy? That was kind of a new thing for me to have like, haters. With “Drag Race” fans, and fans today in general, to like one person it means you have to hate someone else.


Remember when liking Lady Gaga meant you had to hate Beyonce? You can’t hate Madonna and like Lady Gaga! It’s the same thing; you can’t like Kim Chi and Bob the Drag Queen, you have to like one or the other. Well, we like each other!


You have worked with almost every queen out there; I am going to give you a list of queens that are in New York City that you have worked with or know; just give me the first thing that pops into your mind;


Marti Gould Cummings:

Marti Gould Cummings is one of the funniest people I’ve ever met in my life. Certified lunatic.


Judy Darling:

Judy Darling is so clever, so creative and so fucking skinny!


Tina Burner:

Tina Burner right now is one of the most prolific drag queens in New York City. She has changed drag in this town so much.


Pissi Myles

Pissi Myles is so fucking smart, talented and funny and is truly one of the most humble people I have ever met in my life.


“Purse First” is your single and arguably one of the best singles to come out of any of the “Drag Race” girls. What made you want to do such a “Paris Is Burning” inspired track?

Every black person goes through a phase where you are just as black as you can be. Beyonce is in hers right now. She doesn’t want to talk about “Single Ladies’; she wants to talk about “Becky with the good hair” and mixing that “negro with that creole.” Making music that white people don’t always feel comfortable singing. I think I’m in my phase right now. Somewhere around thirty, I said I was going to celebrate my queerness and my blackness. I mean with that “ak ak ak boom” it’s really unapologetic and gay. And it’s not trying to make any qualms or excuses. People asked me about it “crossing over” and I said I just wanted to do a song with me making up the words and that was what I did.


That purse is going to be in Smithsonian at this point.

Do you know I sold that damn purse for $800.00 for charity? I could've held onto it for even more. I think the guy did the AIDS Life Cycle or something and put it in a Ziploc bag on the front of his bike.


What would Bob the Drag Queen, now “America’s Next Drag Superstar,” tell Bob the Drag Queen who walked into the workroom on the first day?

I would just sit back and watch, I wouldn’t tell her anything. I wouldn’t do anything differently, I would just sit back. I think that’s the same advice Bob would give young Caldwell; I wouldn’t give him any advice because I wouldn’t have become the person I became today, you know?


What’s next for Bob the Drag Queen?

Wow, well I am filming a documentary, I am filming a standup comedy special, and I am traveling the world. It’s amazing that I can travel the world and do my bits and try to make the world more aware of the things I find important.