Born and raised in Canada, James Insell created the drag persona of Jimbo and began working in the world of entertainment from an early age. He competed on the first season of RuPaul Charles’ extended franchise, Canada’s Drag Race, where he won Snatch Game thanks to his Joan Rivers impersonation. Jimbo came in fourth place before the end, then made a brief appearance on Canada’s Drag Race’s second and third seasons.
RuPaul’s Drag Race: UK vs. the World came next in 2022 for its inaugural season, and Jimbo was eliminated on the third episode.
The eighth season of RuPaul’s Drag Race All Stars, the following year, proved fruitful as Jimbo was crowned the winner and took home a total of $220,000 in prize money.
These valuable experiences have led the talented performer to a regular spot on the judging panel of Canada’s Drag Race All Stars, with a series premiere later in 2026.
Heading to the Heath Mainstage at The Den Theatre on April 7, Jimbo the Drag Clown is set to balance music, madness and mayhem for an unforgettable highwire act this spring.
Windy City Times: You are looking fabulous on this virtual call.
Jimbo: Thank you. It’s me, Joan Rivers and I am back from the dead. I am coming to Chicago with my all-new comedy show. “Can we talk?” This is my unofficial and unapproved parody tour. I have to say that for legal reasons. I don’t want Melissa Rivers to get any more of my money than she already has, okay?
WCT: The time I interviewed Melissa, she talked so much that Joan could barely get in a word.
Jimbo: That sounds just like Melissa, me, me, me.
WCT: What are your plans for The Den Theatre appearance?
Jimbo: It is a new show and runs about 45 minutes. It is based on my love of Joan Rivers. It’s an all-original set and a tribute to Joan. We cover all of my favorite things with the gays, the “theys” and the lesbians. We talk about current events and celebrities.
I read the audience down for their outfit like the Fashion Police used to do. I have been working with Tony Tripoli, who is an amazing comedian and he was a friend of Joan Rivers. He is giving me the inside scoop on Joan herself, so that is helpful.
WCT: The last time I saw Tony was many years ago on Joan’s tour. Is he coming with you?
Jimbo: He opened for me in Phoenix and it was incredible because he brought Joan Rivers’ ashes to the show. I almost kicked the container full of her ashes over because I fell out of my chair by accident. It was funny, but also an honor to have Joan with us in that way.
I am actually wearing Joan’s earrings right now. I bought them from the Rivers estate, so they were her personal earrings.
WCT: One thing Joan Rivers said was if you like the shoes, then buy the shoes. She was saying not to second-guess yourself and live for the moment.
Jimbo: I like to consider myself a buy-sexual, as in buy me something and then I will get sexual. You don’t have to tell me twice to buy the shoes and the earrings. I love shopping!
WCT: What pronouns do you use?
Jimbo: Check out these gorgeous tits here, so it’s she/her right now, but it depends on the moment when I am he/him.
WCT: What is the biggest size cup that you own?
Jimbo: I have so many sizes, but one of the biggest is my size Z cup. I also have a jumbo pair that is too big to even fit in a suitcase. I have an inflatable pair that is eight feet wide.
WCT: Is bigger better?
Jimbo: When in doubt, go big or go home.
WCT: When did you first start performing drag?
Jimbo: I was interested in drag ever since I was a little boy, when I would play in my mother’s clothes.
I was fascinated with Joan Rivers when I was young and I would watch her on TV. I thought my lunch lady was Joan and there was a mishap when I confronted her. I said, “I know you are Joan Rivers,” and she replied, “No, honey, I am not.”
It wasn’t until later that I started being a clown and I woke up my drag persona again. I started doing impersonations and characters. That is when I discovered my impersonation of Joan Rivers. Professionally, I have been doing drag for about 10 years now.
WCT: Did you ever meet Joan or see one of her stand-up shows before she died?
Jimbo: No. I never met Joan or had the pleasure of seeing her in real life. This is all made up.
WCT: Joan gave me a nice compliment one time by saying, “If you write about me, then I know the gay community will come see my show and I don’t have to worry about low attendance.”
Jimbo: I have that in common with her. I love gay men so much that there’s a gay man inside me right now.
WCT: Aren’t you married to a gay man?
Jimbo: Yes. I am surrounded by them. They are everywhere…
WCT: Not only do you have a gig at The Den, but you are a judge on Canada’s Drag Race All Stars later this year.
Jimbo: That’s right and it was a full circle moment. I made it to the judging panel after two previous guest judge spots. One was on Drag Race Philippines and the other was Canada’s Drag Race a few seasons back.
This is my first full season judging six episodes. It was difficult to judge these queens while being kind and supportive, but also read them as a sister should.
WCT: How was working with your fellow judges, Priyanka and Brooke Lynn Hytes?
Jimbo: We had so much fun tearing each other apart and there was a great dynamic between us. We have a sisterhood that felt fresh because it was the first time in Drag Race history that there was a full drag judging panel.
WCT: Are you in a movie this year?
Jimbo: Yes, The Snake is my first movie and I didn’t make it to Texas for the premiere at South by Southwest. I haven’t seen my performance yet, but apparently it was great. I heard the audience loved it and it has gotten good reviews.
I was sorry to have missed it. I was down in Mexico sunning these buns!
WCT: Do you enjoy the traveling part of your job?
Jimbo: Oh, yeah. I love to travel and meet people. I like to stay in hotels and fly around.
WCT: Is there one item you require in your dressing room?
Jimbo: Prostitutes. I like to have a taste of the local penis. No, I am kidding. The only thing I like to have in my dressing room is some fresh fruit, both literally and figuratively.
Sometimes I like a little soda water and some Colombian cocaine. I’m a simple lady and I don’t need much.
WCT: With these late-night gigs, I am sure it helps you stay awake.
Jimbo: I do what I can to stay up all night.
WCT: Was Pee-Wee Herman a big influence on your House of Jimbo show?
Jimbo: Huge. You can get a sense of my crazy place with the camera.
WCT: Your house looks like a boutique retail store.
Jimbo: My house is filled with puppets, mannequins, costumes and set pieces. People always compare my house to Pee-Wee’s Playhouse.
WCT: How was meeting electronic singer Peaches?
Jimbo: Peaches is like Pee-Wee in the way she has also inspired me for a long time. I saw her 20 years ago and she was a badass performer who would jerk off with a microphone. Her shows were always irreverent, sexy and nasty all at the same time.
The things I love about drag Peaches performs as a punk musician. There are many crossovers between our aesthetic and our style. Making a music video for her song “Hanging Titties” and performing with her at The Bellwether in Los Angeles was a dream come true. She is so fierce and unapologetic. She lets it all hang out.
WCT: Are you releasing music soon?
Jimbo: I worked on the music with Roxxxy Andrews for Jimbo’s Drag Circus, a one-hour special which featured my different drag characters and I hope to release a full album of that music this year. I am also putting out a documentary to go with the show as well.
WCT: What is your all-time favorite musical?
Jimbo: I would have to say my favorite musical is The Rocky Horror Picture Show. I have done the show several times here in Victoria, Canada, with the theater group Atomic Vaudeville. I came up performing with Atomic Vaudeville as a clown, so Rocky Horror will always have a special place in my heart.
I love Little Shop of Horrors and Hedwig and the Angry Inch. I am a big John Cameron Mitchell fan and have watched Hedwig a million times.
WCT: Is there anything more you would like to say about the upcoming Den Theatre show?
Jimbo: It will be amazing and it is about to sell out. It is edgy and I will make people laugh their asses off. Now more than ever, we need humor after all that is happening in the world or we wl just sit and cry because it is all just too much. I hope all of the LGBTQ+ community and our allies will come out for it. I can hardly wait to come back to Chicago and see everyone.
Jump over to The Den Theatre Chicago, 1331 N. Milwaukee Ave., for the joyful Jimbo on April 17 starting at 7:15 p.m. For tickets, visit thedentheatre.com or call 773-697-3830 and plan for a two-item minimum with no clowning around.