When fan favorite Jimbo first competed on the inaugural season of Canada's Drag Race, the comic clown/queen/genius pulled off one of the most unhinged and iconic exits in the Drag Race franchise’s herstory — no doubt speaking for all of North America, on both sides of the border, as he dramatically collapsed on the runway and unleashed a pained, birds-scattering “WHYYYYYYY?????” wail. RuPaul, who got his own start in an '80s punk band called Wee Wee Pole, later cited the exaggeratedly breastplated British Columbian’s disruptive style as proof that “punk’s not dead” (a slogan that, of course, is now emblazoned on various Jimbo merch).
“I was so happy when Ru said that to me as an artist,” Jimbo — whose first memory of being aware of professional drag was “growing up with RuPaul on TV” — marvels. “It was such an honor for Ru to pick up on those bits of my history and what make me a drag performer and performance artist. There is that punk aesthetic in drag, just because it's all about non-conforming and pushing boundaries. It's all about being an artist and an individual and saying ‘f--- you’ to a system.”
Three years later, on his third Drag Race try, Jimbo had the last laugh — or the final “f--- you” — when he pushed those boundaries all the way to the finale of All Stars 8. There, he avenged his previous two shocking defeats (he also controversially stalled in seventh place on 2022’s RuPaul's Drag Race: U.K. vs. the World) and, after lip-synching for his legacy to tracks by new wave/punk legends Cyndi Lauper and Joan Jett, the clown claimed his crown.
But back in 2020, when he was “still kind of feeling a little bit some kind of way about how it all went” on Canada’s Drag Race Season 1 (“I really left the show going, ‘What the f---?’”), Jimbo made a surprising post-punk artistic statement. He enlisted his upstairs neighbors, Canadian production company Studio 549, and paid tribute to another ‘80s artist, with a faithful, shot-by-shot remake of the Buggles’ scrappy, low-budget “Video Killed the Radio Star.”
“I love the idea that that was the first video put out on MTV, and that was one of my first videos that I was putting out to show myself,” Jimbo, now 41, explains. “And I love that D.I.Y. aesthetic. I live on an island of artists, Vancouver Island off the west coast of Canada, and we're kind of known for having to make our own fun, make our own vibe, create fun for ourselves and for each other. And that video definitely has that aesthetic of a bunch of artists getting together and using their strength to create an elevated performance.”
While Jimbo is known as one of the Drag Race ’s greatest comedy queens, as is the case with most many great queens — and clowns — his art is rooted in trauma. “Trauma is all about how you deal with it and how you pick yourself up and how you move on,” he shrugs. “I've had a lot of pain and sadness in my life, but I've had so much joy and opportunity and awesomeness, and I am so grateful and lucky to be able to laugh at my hardships in life and to try my best to learn from them and weave them into my story — so that other people can learn and benefit from whatever I've been through and how I process that. I think there's all kinds of things in life that happen to us that you can be crushed by and devastated by, or you can learn to accept them and weave them into your art.”
As an MTV-raised queer kid watching RuPaul, To Wong Foo, and another big influence, the “emotionally available and spontaneous” Pee-wee Herman, Jimbo was “always curious about drag and beautiful things, shiny things, all those girly things that as a boy in the ‘80s I was told [not to like]. I had to like the color blue and G.I. Joes, and I had to play with boys. But I wanted Barbies! I wanted to be with the girls and all those things," he recalls. "I used to do drag with my brother. We'd steal my mom and my grandma's clothes and my mom's makeup. We'd hide in my basement in a room that was called the Dungeon. It was this kind of forgotten room filled with family s---. And we would hide down there and get our life and live our fantasy and just have fun twirling in clothes and doing something that was ‘bad’ and a secret. We'd have to hide from my dad, who was terrified that he had two gay sons, because my brother’s also gay.
“And so, I used to hide and do my makeup, and all those things as I became a teenager became horrifying,” Jimbo continues. “If my mom ever brought up to my high school friends that I loved dressing in my mom's clothing, that was mortifying. I would just absolutely die. It wasn't until after high school, when I was in university and in an artist crowd and started performing and being a clown, that I allowed myself to start performing in drag and letting that side of myself back in, giving myself permission to do all that. And that took a long time. My first performance in drag was me performing as my evil stepmother. I performed this character called Karen, and it was a bouffant, twisted version of my evil ex-stepmother who had tortured me. It was very cathartic and very fun and wild and twisted, and the people at the show were like, ‘That was so f---ed-up and amazing!’ And that was my first kind of taste of it.”
Jimbo, whose full name is James Insell, actually got his “Jimbo” nickname from his father, with whom he had a fraught relationship. Both of his parents were alcoholics and eventually got sober, but his dad died in 2018 and never got to see Jimbo the Drag Clown in all his grand, grotesque glory. But Jimbo’s mother was always his biggest fan. Recalling his “first taste of feeling flowy,” Jimbo says fondly, “My mom put makeup on my face and I was maybe about 5 or something. I remember just looking in the mirror saying, ‘Oh my God, Mommy, I'm beautiful!’ And she said, ‘Yes, you are, baby.’ And ever since I had sort of a fascination around beauty, and then being a little rebel and being who I am. When you're told that's ‘not for you’ or ‘no, you shouldn't like that,’ it kind of makes it extra-exciting.”
It's that extra-exciting element of the twisted and the forbidden that is the throughline of Jimbo’s underground art, whether it’s his freakish silhouette proportions (“Bodies are bodies and people are people, and there are all kinds of ideas of feminine and masculine”) or his obsession with scary clowns (“I love things that are meant to be beautiful or happy, but through the process of painting or whatever it is, they become creepy”). And then there was his Whatever Happened to Baby Jane?-inspired Snatch Game impersonation of pants-pooping “faded starlet” Shirley Temple (“There's something so tragic and intriguing about a child star that never outgrows their childhood fame”), which made the usually unflappable Kandy Muse break character and probably clinched Jimbo’s All Stars 8 win.
Jimbo explains that “clowning is all about being really present, and it's all about throwing away your expectations of what you're going to do and being open to the possibilities of what could happen. … It’s all about showing up, allowing yourself to be seen, and going with your ‘worst’ idea in the moment,” and he reveals that he didn’t put much planning into his now-legendary Temple impression. “I didn't even know I was going to tap-dance. … I strapped those on my feet and I just made it all up on the spot,” he chuckles.
Jimbo presumably put a bit more rehearsal and thought into his current Jimbo’s Drag Circus tour, which runs through June. The tour resurrects Shirley as a hip-hop comeback star rebranded as “Sweet T,” along with five other characters, including Jimbo's other iconic Snatch Game impersonation, Joan Rivers, in a “fallen angel number” complete with backup dancers.
There's no “Video Star” number in the revue, sadly, but Jimbo and his collaborator Andrew Fields have composed a full score for the show and are writing new music while on the road, so perhaps the Buggles’ super-producer Trevor Horn, who is aware of Jimbo’s "Video Star" homage, will work with Jimbo one day on original material.
“Oh my God, pull some strings!” the punk clown laughs, when the idea of a Horn collab is brought up. “I'm a storyteller and I love singing, and it kind of makes sense that those kind of go hand-in-hand. And so yeah, I really would love to put out more music and make more music videos.”
In the meantime, tickets for Jimbo’s Drag Circus tour are available here, and his full interview with Music Times can be viewed below.
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