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Bob the Drag Queen – An Education in Labels, Terms, and Ideas

WRITTEN BY |  AUGUST 4, 2020

I had wanted to spill the tea with Bob the Drag Queen about backstage shenanigans during RuPaul’s Drag Race, how heavy the winning crown is, how big his closet is, who the biggest diva on “We’re Here” is, and who is his celebrity crush.  We didn’t even get there, and I am so grateful.  With all the glitter and snappy one liners in the drag world and Drag Race memes being as popular as Black Lives Matter ones, we can easily be distracted and forget that rallying against the tornado that is our current social and political climate is not just on a given day or given holiday, it is a constant battle.  Bob the Drag Queen knows, and he has a lot to say and has the personal experience to say it.  With pop culture entertainment personalities running for President, why not Bob the Drag Queen?  Hearing him talk about our current situation is a breath of fresh air.  He makes sense, he’s got the receipts, and he’s got my vote.

Before Bob the Drag Queen was a drag queen, he was Caldwell Tidicue the Activist.  He moved to New York with two suitcases and $200 to follow his dreams to be a stand-up comedian and actor.

How did you get involved in activism?

I first got involved with activism, like in activism the way that people call it activism, in New York City with a group called Queer Rising. They’re this group, a little bit like Act Up, but obviously much later in time, and we would do different demonstrations to cause a scene somewhere and bring awareness to something, get arrested, block traffic, pull basically public stunts in an attempt to bring awareness to different issues in the queer community.

His first drag name, Kittin Withawhip, was based on a 1964 crime drama featuring Ann-Margret as juvenile delinquent with a sexy side.  No one really said the name right, so Caldwell decided to keep it easy, three letters, B O B – and Bob the Drag Queen was born.  You can still search early performances of Kittin Withawhip on YouTube, and I highly recommend that you do. Kittin had a certain irreverence to drag culture but also a respect for it as well.

Bob’s mom owned a drag bar and he would often accompany her when the babysitter didn’t show up.  He bought his first makeup kit shortly after watching Season 1 of RuPaul’s Drag Race.  And now, from New York drag scene performer to winner of Season 8 of RuPaul’s Drag Race to producing and co-starring in HBO’s critical and audience hit “We’re Here,” his brand has expanded to include podcasting, music, and spokesperson for the Queer Black Movement.

How has drag changed Bob the most?

My very first day in drag I was 22 years old, I had been living in New York City for a little less than a year. I’ve learned a lot about myself since then – as a black person, as a queer person, as a non-binary person, as a New Yorker, as a son, as a mentor.  I’ve certainly learned about the impact that I can have. I’ve always thought that I had a great potential, but I’ve seen that maybe I could have even more of an impact on people then I thought I would, and I’ve started to choose my words and my actions a lot more wisely than I used to.

At the end of June, Bob the Drag Queen and Drag Race personality Peppermint, led the first ever Black Queer Town Hall with GLAAD and New York Pride.  The three-day digital event featured Todrick Hall, Pose’s MJ Rodriguez, Laverne Cox, Alex Newell, Angelica Ross, Monet X Change, and many more. “I have noticed that there is a certain reverence being given to black queers right now. And to be frank, it feels new. And I think that we in the black community are still adjusting to this. I was watching the Chicago Drag Council on our Town Hall and seeing how uncomfortable some of the white people looked to see black people in power. They were shook, they were shook to have it happen. It felt odd. It’s interesting that the closer you get to equality, the ones who are in power start to feel oppressed. And, it is true they say there is no equality without loss of power. I believe that with every fiber of my being.”

Talking to Bob was an education in labels, terms and ideas that are not quite as explored in my West Hollywood bubble.  This current social environment has been a big education as to how people want to be identified and labeled.

Can labels be limiting and overall harmful to the LGBT and other minority communities?

I don’t think that labels are new to our community. Like, yeah, I’ll admit there were less labels, or less labels being acknowledged. There’s also an idea that all this language is brand new, and that’s not completely true. People would have you believe that terms like cisgender or pansexual, or, you know, non-binary, are words that just popped up in the last two years, but that’s not a true statement. And are they harmful to the community? I certainly don’t think so. I think they can be used to harm people if you’re intentionally misgendering or intentionally trying to identify someone in a way they don’t identify. But I feel like the idea notion of labels, ideas and pronouns are helping people communicate better and helps people feel safe. And that’s why I always tell people to put your pronouns in your Twitter bio. Even if you are a cisgender person who uses the pronouns of the gender you were assigned at birth. It also signals to people who may be crossing your path that you are a safe person they can talk to.

How do you feel about being part of the RuPaul’s Drag Race family that automatically inducts you in the firestorm that social media can become?  Even RuPaul himself is often questioned as to his social media presence or lack thereof in acknowledging Black Lives Matter and Trans Black Lives Matter.

There are a lot people out there who really seem to have problems with social media activism, and honestly, it really doesn’t bother me. It just doesn’t.  I’m also not one of those folks with a vendetta against the cell phone. You know some people were like, ‘We gotta get off our phones!’ I don’t necessarily see it that way.  How I see the phone is like you’re holding this device in your hand that has the answer to every question in the world.  It’s a powerful tool. Good and bad is subjective. So, whether you can say which ways are good or bad, it is up to each person individually. I wouldn’t say it is an influencers duty to become politically involved, but I do know that as I became more aware of myself in my community, I felt it was MY duty. So, I can’t obviously decide what other people’s duty is. But I know how I wanted to use my platform as it grew larger and larger. And should we be calling people out who don’t use social media to make a statement? You’re allowed, like I believe, in freedom of speech. You have the freedom to not say anything. I have the freedom to mention that you have not said anything regarding my struggle. So, if you’re going to exercise your freedom, I’m going to exercise mine too.

Comedy is a big part of Bob’s personality and portfolio.  His comedy style, while hilarious and effective, has a bite to it.  Fans are as likely to pay attention to his comedy as much as his current drag look.  To date, he has produced two one-person shows, Bob the Drag Queen: Suspiciously Large Woman for LOGO and Bob the Drag Queen: Crazy Black Lady for OutTV.

Do you feel the pressure to be politically correct, especially now?

I don’t believe in policing people’s art and telling comedians what to do with their platform. But then again, that goes the same in my direction. My art is comedy and I have realms of expression in oration outside of comedy as well. So, if part of my expression of art is mentioning how your art is problematic, then you’re going to have to accept that too. I know it sounds like a Catch 22, but if your comedy transgresses a community and that community mentions it, I find it so odd that people would be mad that someone got mad about something they did. The oddness of being offended that you offended someone and that they mentioned it is backwards to me.

His hit show on HBO, We’re Here, was renewed for Season Two.  The original six-episode season was released for Pride Season and features Bob alongside other Drag Race alum Shangela and Eureka O’Hara travelling to small towns across America, inspiring local residents to share their stories and express themselves through a performance of uncensored drag.

The series was very well received and explored the world of drag in an extremely, and sometimes devastatingly, intimate way.  What does “We’re Here” mean to Bob?

I think “We’re Here” is as a double entendre. I mean, when Eureka, Shangela, and I show up in town with these humongous vehicles, like we’re literally here, but also, it’s an indication that we, the queer community are already in these spaces. Some people may not think of Gettysburg, Pennsylvania and the queer community that exists there or Twin Falls, Idaho, but there’s also a thriving drag scene in Twin Falls, Idaho, and maybe people don’t know about it. So, we’re here to uplift those voices and to amplify those voices.

How is the show different from other drag shows currently saturating TV screens?

Well, “We’re Here” is different for a lot of reasons. One, I’m one of the faces of the show and have a producer credit, so we have a lot of say in the creative aspect of the shows and HBO and IFC really let us take the lead on the creative direction of the drag, everything from the look, to the performances, to the staff that makes our garments and hair. And I think you can see that in the show, which is why our drag is so authentic.

What do you want most from Season Two?

In Season Two, I want our inclusivity to go further. I’m so proud of the fact that we were able to include indigenous voices, black voices, Latinx voices, Asian voices, trans voices, ally voices. I was so happy that we were able to do that, but let’s go further. Let’s reach more people. I would love to go international at some point.

I do realize how deep my conversation with Bob got, but I still had to know who the biggest diva on “We’re Here” is.

In all honesty, I think that I’m probably the biggest diva, and that’s not a pageant answer.  If you watch the show, I’m usually the one who’s not smiling. I’m the grumpiest. Definitely the grumpiest out of the group. If we were The Golden Girls, but only three – I’m Dorothy. Like, DEFINITELY Dorothy.

You can hear more of my chat with Bob through our podcast, Metrosource Minis, available on Apple Podcasts, Spotify, iHeartRadio, YouTube and Metrosource.com. (Photos courtesy Bob the Drag Queen.)