How this veteran Canadian rocker and ‘Mayor of Kingstown’ TV star is keeping the music savage
Dec 06, 2025
The Toronto Star here
There might be no such thing as a Fountain of Youth, but if there’s a Fountain of Perpetual Bile out there, the Headstones appear to have tapped into it.
Three-and-a-half decades on from the band’s formation in Kingston in 1989, there’s been absolutely no lessening of their powers — nor their general punk-rock surliness — onstage and in the studio, which isn’t bad for an outfit whose founding members now hover around the age of 60.
The rock ’n’ roll law of diminishing returns simply doesn’t apply to the Headstones. Since reforming in 2011, after an eight-year hiatus brought on by the usual excesses and egos, they’ve cranked out a half-dozen albums that easily stand shoulder to shoulder with the rippin’ Cancon radio staples that made them a household name at the peak of the alt-rock era: 1993’s “Picture of Health,” 1995’s “Teeth & Tissue” and 1997’s “Smile & Wave.”
The last Headstones record, 2022’s “Flight Risk,” was the most savage thing they’ve ever done, backed up by shows so fierce, you’d swear a pack of hungry young hardcore kids in their 20s was prowling the stage.
And now we have “Burn All the Ships,” which was issued via venerable Toronto indie imprint Dine Alone Records in September and plays exactly like the ambitious, nuanced Big Rock Record everyone dreamed the Headstones would make as a capper to that masterful mid-’90s run, complete with cool-kid guest appearances from Metric’s Emily Haines and Dallas Green of Alexisonfire and City and Colour.
They’re bucking the trend, you might say. But when have the Headstones ever really paid attention to trends?
“I’ve always come at the band and the music as a fan,” offered vocalist Hugh Dillon, a youthful and long-sober 62, speaking to the Star from Los Angeles a few weeks ago. “From the beginning, we wrote our asses off, we played everywhere, we rehearsed all the f—kin’ time and even amidst all the chaotic drunkenness, there was that work ethic. Even in our worst shape, we could still deliver and transcend the chaos.
“The truth of the matter is, with most bands the records don’t get better. And I always wonder ‘Why is that?’ You would think that if you learn your craft and work and work and work — in any other aspect of life, the idea is that practice makes perfect. But sometimes bands just lose their way, or the individuals involved don’t have the same interests.”
In the case of the Headstones, the members have remained close friends and retained a real work ethic. “On some level, it isn’t work,” Dillon said. “It’s a way to communicate with people you trust. We don’t play f—kin’ golf, so this is a way for us to further that relationship. We genuinely like what we do. It’s very simple.”
The fact that Dillon — who may be better known these days as the star of Bruce McDonald’s nihilistic 1996 cult classic “Hard Core Logo” and a fixture on such TV series as “Flashpoint,” “Durham County” and “Yellowstone” than as the lead singer of a ferocious rock band — still makes time for the Headstones amid an insanely busy schedule as an actor, writer and producer in Hollywood speaks to the band members’ deep friendships and shared enthusiasm.
When we last spoke, Dillon was mired in post-production for Season 4 of “Mayor of Kingstown,” the gritty Paramount Plus prison drama he’s conjured with “Yellowstone” creator Taylor Sheridan and ace actor Jeremy Renner. It was clear, however, that Headstones occupy a position of equal importance in his life.
The opportunity to get back on the road with childhood friends and band co-founders Trent Carr and Tim White, keyboardist Steve Carr and relatively youthful newish drummer Jesse Labovitz this fall just brings the promise of … fun. A lot of laughs and fun. Dillon wouldn’t be doing any of this stuff if it wasn’t fun.
“It’s all just s—t that you’re interested in and sometimes you get lucky,” he said with a shrug, conceding that a certain amount of rigorous scheduling is involved to make everything happen all at once. “The opportunities are just so exceptional that you’d be a fool not to rise to the challenge.
“You just like the artists you’re working with. It’s not work, in that sense. And that’s why you can do it. With the touring, I really love playing Ontario and B.C. and Alberta and Quebec. And I love the bands we’re playing with and the fans coming to see us after we haven’t played in awhile.”
For Dillon, it’s all just exciting. “It’s that excitement that’s always drawn me to this kind of world and this kind of life. I’ve always had a low boredom threshold. My mind was always a ‘bad neighbourhood,’ I’ve been told. So it’s good for me just to keep busy. It’s creative and it’s your own creation, so you’re driven to make it great. This is me. This is what I do. This is who I am. So I don’t wanna f—kin’ phone in any dumb s—t.”
The Headstones return to the Toronto stage on Friday, at the Great Canadian Casino Resort with the Tea Party and Finger Eleven. It’s the live shows, above and beyond the recordings, that keep the band going.
They’ve had some radio bangers along the way, but they were lucky enough not to go stratospheric and have their own “Smells Like Teen Spirit” hung around their necks like an albatross. The Headstones fans are fans of the Headstones, not of one monster single. They’re coming out to hear the catalogue. It’s the right level of infamy, according to Dillon.
“We’ve had records that do well and records that don’t do well, but at the end of the day, the two entities that like them are the people in the Headstones and the fans of the Headstones. And that’s kind of it,” he said.
“It’s like the Replacements or Social Distortion for us here in Canada. We just have a core following who grew up with us and who knew us because, at the end of many shows, we would drink with our fans or go to our fans’ houses — which is a different beast from being separate from your fans, where you’re so big that you’re escorted in and out. Then you’re in it for other reasons. We’ve always felt very lucky that this is what we do. So after the records, it’s important to give it 110 per cent live. Because if people don’t come to see you live, then it really doesn’t matter. Then it’s all smoke and mirrors.”
And what of the appearance of Canadian indie-rock leading lights Haines and Green on “Burn All the Ships”? For a pack of miscreants who’ve never been, as bassist White recently put it to me, “darlings of the media,” it must be nice to know that some of the heirs to the Headstones’ DIY-and-damn-the-torpedoes throne were listening all along.
Haines wobbled into the studio on a broken foot to contribute what she calls “one hell of a duet” with Dillon on the straight-up ripper “An Effort to Forget,” while Green — as Dillon puts it — “effortlessly and gentlemanly” wandered into Dine Alone’s east-end offices from the studio across the street to suggest adding some harmonies and musical colours to the anthemic “Navigate.” The band members weren’t planning on bringing any outside star power to the proceedings, but they were chuffed that the label made it happen.
“It’s just exceptional when people bring that kind of brain power to a project,” said Dillon. “It’s such perfect chemistry, and who would have thought that? But there’s a like-mindedness with Emily and Dallas. Their bands have done the same thing (as ours). They’ve carved their own paths, they’ve kept their heads down and they just do their own thing. And they’re unique in that way. So when you get to work with these folks, you find these similarities, and it makes it profoundly gratifying when you get to the end and you listen to the album and you’re excited to hear their contributions. They elevated everything. We didn’t see it coming.”
For Dillon, that kind of luck and timing is all part of the work ethic.
“We stay at it and stay at it and we don’t expect anything from anybody,” he said, “so when we do get a break or somebody gives you a leg up or helps you out or encourages you, it’s really neat.”