For three of the five years that the Winterruption art and music festival has been running in Edmonton, Top 40 Under 40 alumnus Brent Oliver has been trying to book a specific artist. Kool Keith, Oliver says, is a legend in the alternative music scene, and Oliver just really wanted to see his name on the long list of over 100 unique, alternative music, comedy and drag artists to perform on over 10 stages around Edmonton from January 22-25.
But each time he was asked, the American rap artist simply said, he didn’t have a passport. This year was different.
“Out of the blue, I think it was in April, I got an email from Kool Keith saying: ‘Hey man, here’s a scan of my new passport.’ And I was like, ah, I guess we’re booking Kool Keith!” says Oliver.
Oliver works with a board of 11 others — including a school teacher and government employee — to book the artists, coordinate hotel bookings, organize transportation for the artists, ensure alcohol is delivered to the venues and all the jobs in between. And it’s all on a volunteer basis.
“When I was younger, I think putting on shows was like: Hey, I’m hosting a party. Or, it’s almost like that friend who’s like: Hey, you’ve got to hear this. That’s turned more into doing it for the community,” says Oliver.
Winterruption happens in many other cities and Oliver says it’s a great way to bring people together during the winter — and it works well as most artists are available in January when they have breaks from touring.
The show aims to be as inclusive and diverse as possible. “Nothing drives me more crazy than seeing a festival lineup replete with white guys with guitars. It would be really easy to phone this in. But that’s not what 2025 should be or requires, so it’s super important to me,” says Oliver.
The lineup is full of unique bands — Winona Forever has a retro and catchy pop feel; Iron Tusk is an Indigenous punk metal band from Calgary; Badge Epoque Ensemble is a Toronto jazz/funk collective; one of the headliners, Cheekface, plays indie pop songs that Oliver says “will get stuck in your head for days.”
Cedar T, an Edmonton Indigenous drag queen will also perform at the festival as well as Celeste Lampa, a first generation Filipino-Canadian mom, wife and comedian.
And this is just a small sample of the lineup. “I ask agents: who’s your hot, up-and-coming acts? They pitch to me, then I go back to my teenage kids, the board, and just people younger and hipper than me and we discuss it,” says Oliver. “One of the great things about booking these days — I’ve been doing it so long, I used to have to get sales numbers of their cassettes and CDs from Sam the Record Man on Whyte Avenue in the ’90s. Now, you can just see how many social followers they have, how many Spotify followers and just get data that way.”
He also consults with organizations like the Fruit Loop Society of Alberta, which provide special initiatives for Alberta’s 2SLGBTQ+ community along with other BIPOC 2SLGBTQ+ promoters. With over 100 acts in the festival, it’s quite the process to secure the lineup each year, but Oliver enjoys it.
And it’s really important to him and the board to make the festival as financially accessible as possible. The price of tickets is lower than most festivals, which means it relies on sponsorships and grants to operate as a 100 per cent volunteer-run initiative. Even so, Oliver wants to be sure everyone can share in the unique experience. “I make sure every year we not only have all ages shows, but also we have a number of free events happening throughout the weekend,” he says. “So if you can’t afford a show or a wrist band, go to a free show.”
Occasionally, Oliver gets people complaining they don’t want to pay to see a bunch of unfamiliar bands. But he argues that should be part of the appeal — people can go and discover all kinds of amazing talent they did not even know existed right at one festival.
Hear something new that appeals to you at this year’s Winterruption.
