Bob the Drag Queen Spills on Madonna, Novel Writing, and a Controversial Oscar Party Moment

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Bob the Drag Queen, originally known as Christopher Delmar Caldwell, has left an impressive mark on his path ever since he emerged victorious in the eighth series of “RuPaul’s Drag Race.

He’s performed alongside Madonna, established himself as a credible figure in the demanding world of stand-up comedy, and also managed to make an appearance on the American adaptation of The Traitors – the reality show that dethroned RuPaul’s Drag Race from its Emmy reign.

Currently, the intellectually agile and renowned figure, aged 38, is venturing into more sophisticated realms with his inaugural published novel titled “Harriet Tubman: Live in Concert“, which is now available from Gallery Books.

A novel that reimagines history by bringing back a legendary figure who fought for freedom, alongside other revered personalities from the past, this time in modern times. In an unexpected turn of events, he’s tasked with creating a hip-hop album, and it has been highly acclaimed by critics.

This new achievement is simply another beautiful adornment on Bob’s versatile collection of accolades, whether it be a hat, wig, or handbag – take your pick, first! He had an engaging conversation with The Hollywood Reporter, discussing his fiction writing, collaboration with Madonna, and his consistent phone availability.

Hello there, Bob! It’s possible you might recall our previous encounter. We had a chance meeting at the Hollywood Reporter office and on that occasion, you were accompanied by Kim Chi.

Hey Bob! Do you remember our past encounter? You visited the Hollywood Reporter office with Kim Chi as your companion. Hope this jogs your memory!

Wow, it seems we’re revisiting an old moment, isn’t it? That time with Billy Bush, you, Kim Chi, and Naomi Smalls had him dress up in drag. I believe this happened prior to the Access Hollywood scandal breaking. A few years down the line, we found ourselves saying, “Look at that…,” didn’t we?

The scandal happened first, followed by Donald Trump’s initial victory. At that time, many people didn’t believe he would actually win. I recall asking for your advice if he did win. Your response was insightful. You suggested staying in the country and fighting instead of leaving it.

Absolutely, and despite understanding if others choose to depart, the urge to do so is immense. However, my forebears labored and even sacrificed their lives to establish this nation. Therefore, I have no intention of relinquishing my place here. I’m claiming my rightful share.

I believe it’s crucial that individuals such as yourself are out there, standing up, advocating, and performing your roles.

Thank you. That’s what it’s all about. I’m just a loud mouth who can’t shut up.

It’s been a little over eight years now. How far have you come since then, in your own estimation?

Over the past eight years, I’ve been quite busy. I starred in three seasons of a show called “We’re Here” on HBO, which was fortunate enough to receive a Peabody and three GLAAD awards. I’ve also filmed two comedy specials, with my third one currently in progress. I had the opportunity to tour with Madonna, as I hosted her world tour. Additionally, I filmed “The Traitors”.

I’ve experienced quite a bit too. Last year on Mother’s Day, I unfortunately lost my mother. Incredibly, that was the day. My nephew now resides with me. To add, there’s a straight male in my household as well. Furthermore, I’ve recently relocated to Los Angeles, California. Needless to say, much has transpired in these eight years for me.

Do you still enjoy doing drag?

I’m deeply fond of it. The dress I earned on RuPaul’s Drag Race is proudly showcased behind me. Drag holds a special place in my heart, and it’s one of the things I’m most passionate about. Besides drag, comedy, social and civil rights are other passions that ignite my spirit. Drag has played an instrumental role in shaping who I am today, essentially providing me with everything I have.

You brought up ‘The Traitors’, but I didn’t catch your previous season. I did catch the second one though, and I believe my decision not to return was partly influenced by how Peppermint was handled during that run.

To put it another way, while I wasn’t exactly in the same situation, I managed to stay a tad longer than Pep. My journey didn’t take me too far, stopping at just four episodes. However, my role was that of a villain, or rather, a Traitor. I do have a flair for the dramatic, so I gave them quite a challenge on that particular show.

Did you have a good time doing it?

It was a challenging period for me, as I had to attend my mother’s funeral just a week before going to Traitors. It was quite overwhelming with all the arrangements. If only I could have handled it at a less stressful time in my life, that would have been ideal. However, things don’t always go as planned, and I managed to do it when I had to.

Let’s talk about Harriet Tubman: Live in Concert. I really enjoyed it.

Appreciate your attention! My first novel is receiving fantastic feedback, which I’m truly grateful for. While I may not hold a PhD in literature, I’ve always viewed myself as a writer at heart. For the past 16 years, I’ve been crafting standup comedy routines, but transitioning to writing a book proved more challenging than anticipated. It took me a full four years to complete that novel.

First of all, the way it was packaged is incredibly enticing. It’s a great cover.

Those are indeed Harriet Tubman’s own hands that you see. She isn’t pretending to hold a microphone; instead, she is simply interlacing her fingers.

Well, you might find the topic intriguing, though it’s not your typical action-packed gaming read. Instead, it delves into the realms of history and music.

In addition to the topic of freedom, which is prominently explored in the book, I’ve been captivated by Harriet Tubman’s tale for quite some time now. The feats she accomplished seem almost unbelievable. Moreover, I’m a fan of hip-hop music and felt compelled to merge two things I adore into a single narrative. Consequently, I set out to create a book that embodies this fusion and appeals to my own reading tastes.

The theme of freedom is significant in the book. For years, I’ve been fascinated by Harriet Tubman’s life story. It’s amazing what she accomplished. I also enjoy hip-hop music a lot. So, I wanted to combine these two passions and write a book that brings them together. I wanted to write a book I would want to read myself.

To be frank, I found myself receiving proposals for a book deal even prior to having a concrete idea for the book. They approached me with the question, “Would you consider writing a memoir?” But honestly, I wouldn’t have been interested in reading such a book myself. I’ve only read a handful of memoirs throughout my life.

Did you read RuPaul’s memoir?

As a devoted fan and proud gamer, let me share my personal take on some captivating reads that have graced my bookshelf. I’ve had the incredible privilege to delve into RuPaul’s first memoir, “Letting It All Hang Out,” which is an outstanding book. I even own a signed copy of it, and before I stepped onto the Drag Race stage, I was fortunate enough to get her autograph on that very book.

Additionally, I’ve spent some quality time with Michelle Visage’s “The Diva Rules.” And now, I’m diving deep into RuPaul’s second memoir, “House of Hidden Meanings.” Although I’m still making my way through it, I can already tell that it’s going to be another enlightening journey.

Frankly speaking, my life isn’t exactly thrilling. I don’t indulge in alcohol, I shun parties, and dining out is not my cup of tea either. Instead, my days are filled with crafting jokes, sharing them, and then repeating the process all over again once I step off the stage.

Enjoying success involves visiting trendy spots, securing a great seat, and immersing in the atmosphere. Yet, it seems like this isn’t typically how you prefer to spend your time?

To be honest, I do enjoy attending house parties. However, it’s only once a year that I get to go to a big bash like that. And guess what? That annual event is the same one I’ve been going to for years.

Is it Madonna’s Oscar party?

Tonight’s event is Madonna’s Oscars party. Additionally, I may attend my friends’ game nights. I truly enjoy game nights.

Speaking of Madonna’s party, how was it this year?

At this year’s party, I had an absolute blast. Since there were no cellphones around, no photos or videos were taken, which was quite refreshing, despite my constant internet presence.

It caught everyone off guard when Karla Sofia Gascón expressed gratitude towards Madonna for showing kindness to her and extending an invitation to the party. By any chance, did you run into her at the gathering?

I did not. I didn’t watch Emilia Pérez. And also, wasn’t she racist on Twitter?

Something like that.

She’s like a monster on Twitter, so I was like, “Maybe I won’t meet her.”

In a stand-up performance I watched, someone asked about Madonna. You responded, and I’m putting it another way, “At times, she gives off an aura of being the most stylish and amazing individual who has ever lived. Other times, she seems like the ultimate representative of the baby boomer generation.

Just as one might feel starstruck speaking with a pop icon, such as the Queen, and then realizing they’re conversing with a mother of six – that’s the kind of contrast you’re referring to. It’s like moving from the extraordinary to the ordinary in an instant.

I did see you on that tour. It was amazing. You were more than just an emcee.

Apart from being involved in its creation, she placed a great deal of faith in me. Madonna herself stated that when she looks at me, it’s not just the drag queen from “Drag Race” she sees. Instead, she perceives me as an artist, a creative, and someone she trusts implicitly to assist her in crafting her 40-year retrospective exhibit.

How did she discover you?

Lola, her child, is an avid fan of Drag Race. For quite some time now, Lola’s Instagram profile picture has been that of Michelle Visage. I suspect that Lola might have introduced me to her, and vice versa. Then, Madonna delved into a rabbit hole, watching all my YouTube videos. She exclaimed, “Wow, this person is so amusing, clever, and inventive!

One day, unexpectedly, she phoned me out of the blue. I took the call and it was Madonna on the line. That’s how I ended up on “We’re Here”. I received an unsolicited call from the creators of “We’re Here”. I usually answer my phone because I am quite comfortable ending calls if I don’t wish to chat. If I don’t want to speak with someone, I will simply hang up. See you later! Click.

Is that good career advice would you say? “Always answer your phone.”

I consistently pick up the phone whenever it rings. However, it’s not my place to dictate how you should live your life if you’re feeling overwhelmed. I am always ready to take calls. Yet, I have no hesitation in ending conversations with someone at any time.

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2025-03-26 01:25