Spotlight: Jessie James
THIS is DRAG - SPOTLIGHT 024 / SEPTEMBER 2025
Jessie James
Curated by Kevin Blondin
Photos by Taylor Long, Quinton Cruickshanks, Holly Clausius, Ashlyn Daisy, and Andrea Hunter
For September’s Spotlight on THISisDRAG.com, we meet Jessie James, the Hamilton-based drag artist who proves drag can be punk, femme, and fearless all at once. With seven years in the game, Jessie’s aesthetic is DIY at its core—frankensteined thrift finds, patches, studs, fishnets, and PVC stitched into genderf*ck silhouettes with a punk heart. They’re just as likely to belt Alanis live on stage as they are to turn a mullet moment, blending performance, costuming, and grit into one unforgettable package.
Sex, Femme, Punk
Who is Jessie James?
A drag name inspired by Pokémon’s iconic Team Rocket duo, Jessie James is all about campy rebellion with queer power at its core. “They’re one of the gayest cartoon duos IMO,” Jessie laughs, and the name stuck. At 27, with seven years of drag under their belt, Jessie has built a persona that’s punk, femme, and undeniably sexy.
Aesthetic & Inspirations
“My aesthetic is very genderf*ck, punk, grunge, ass almost always out (when appropriate of course),” Jessie explains. Their drag leans on thrifted and reimagined looks: “I will sooner thrift a few things and Frankenstein them together as opposed to buying a new costume online.” Their wardrobe is heavy on patches, chains, studs, fishnets, leather, and PVC—classic punk staples infused with queer glamour. And a lot of mullets, mullets, and more mullets.
Biggest inspirations? Lady Gaga and Sam Smith, whose artistry and unapologetic self-expression echo through Jessie’s own drag.
The Work Behind the Glam
Drag for Jessie is more than performance—it’s the joy of blending multiple art forms. “It’s performance, it’s costuming, it’s makeup, wigstyling, etc. I love getting to combine so many of my hobbies into one thing and also being in charge of everything really. I’m the director of Jessie James which is awesome.”
Their toolkit essentials include Mehron clown white (“I use it so much, aha”) and NYX Epic Ink liquid liner.
Queer History, Community & Besties
Deeply connected to drag’s place in queer history, Jessie looks to icons like Sasha Velour and Gottmik: “I respect Sasha a lot for her artistry, and also her willingness to uplift all kinds of drag artists through Nightgowns.” History, to Jessie, is not just important—it’s survival: “It often gets forgotten or erased.”
Community is vital too. Their drag bestie and drag kid, Ricky Mania, is a creative partner. “The way he looks at drag and the art he creates… is always soooo cool to me. I love having someone to bounce ideas off of, especially my zanier ones.”
“My drag is sex, femme, punk—and sometimes my ass is almost always out.”
Best Memories & Achievements
When asked about favorite memories, Jessie recalls the first time they sang live in drag—opening for Kylie Sonique Love. “It was packed, hot, and sweaty. I forgot half the words but it didn’t matter because it was Alanis Morissette and everyone else knew them. Something about it was magical.”
Their biggest achievement so far? Graduating from a demanding music theatre program during the peak of COVID. “I had to talk myself out of dropping out a lot, so I’m very proud of myself for finishing.”
Staying Punk, Staying Visible
If there’s one message Jessie wants their drag to communicate, it’s this: “Stay punk, stay sexy, stay queer, stay visible.” Visibility matters, especially for those who can’t always be open. Jessie embraces drag as both a spotlight and a shield.
Looking ahead, they see themselves touring more, developing drag-lesque performances, and pitching acts to festivals across Canada. “Travelling more, doing more music-related stuff, maybe another theatre show or two.”
Always Performing
Jessie is always on stage in Hamilton, Toronto, and beyond. With House of Adam and Steve, they co-host a monthly themed drag brunch at Bernie’s in Hamilton alongside Karma Kameleon. “It’s the first Saturday of the month, every month is a different theme, and during the warm months we get to use their patio!!”
HELLMOUTH - THE BUFFY DRAG BRUNCH
Saturday, September 13, 2025
At Bernie’s Tavern - 1103 Cannon St E, Hamilton, ON
TICKETS
Whether belting Alanis live, strutting in a DIY punk look, or serving monthly brunch realness in Hamilton, Jessie James is drag at its most raw and rebellious. Fierce, femme, punk—and always visible—Jessie proves that drag isn’t just art, it’s resistance. Stay cool. Stay weird.