Hugh Dillon, actor and musician, is having a banner year on both fronts. Mayor of Kingstown, the show Dillon co-created and stars in, returns for a new season. At the same time, his band Headstones — an iconic part of Canada’s alt-rock scene — dropped a new album, and they’re heading out on tour this month.
Dillon calls this moment “a super creative year.” The artist who once balanced acting auditions and rock gigs is now leading two major creative forces.“The show’s out, the tour’s coming — it’s funny that both things are coming out at the same time,” he says, a hint of bashfulness creeping up. “I’m just super proud.”
With Mayor of Kingstown, Dillon is taking stock of just how far the series and his creative journey have come. The gritty crime drama starring Jeremy Renner and which Dillon built alongside Yellowstone creator Taylor Sheridan, is set in a fictional Michigan town where prisons dominate the economy. It has cemented itself as one of television’s most unflinching looks at power, corruption and incarceration. And for Dillon, those themes are deeply personal.
A Kingston boy, Dillon has first-hand experience growing up in a “prison town,” thanks to the looming Kingston Penitentiary. It’s what led him to pitch the show to Sheridan, who loved it, with much of it taking inspiration from Dillon’s memories.
“Growing up, I was a latchkey kid,” he says, in his signature soft and steely voice. “You’d read about serial killer Clifford Olson, for example, who did horrific things. Then realize, ‘Oh, he’s five blocks away in the penitentiary.’ When I was a kid, my dad drove me to hockey practice at 5:30 in the morning at Harold Harvey Arena. We’d pass these penitentiaries that are beautifully lit, this old architecture. And the curiosity for me — what is that place, who are these people? —just never left.”
That early fascination continues to guide the arc of the series. This season, Dillon says, pushes further into “the intricacies of human emotion, how people exist under traumatic circumstances.” He and Sheridan wanted to explore not just violence or corruption, but the fragile humanity within systems that perpetuate them. “What makes people tick? What makes people keep their darkest impulses in check?” hey says. “That’s always been the through line. Taylor taught me to leave everything on the field, work with velocity and don’t let anybody see what’s coming. So, there is a quality in this particular season that has transcended each of the other seasons in terms of unpredictability.”
Authenticity, for Dillon, isn’t a challenge, but a necessity. “I still have a lot of connections with people,” he says. “There’s a consultant that I use from the penitentiary. I’ve had friends who’ve had experiences, both as corrections officers and inmates. I have had my own experiences with being a heroin addict up until 20 years ago.” That lived truth, he adds, is protected by the people he collaborates with. “Taylor has got a great bullshit detector. So does Jeremy. I have great people to work with to construct, in my world, a cinematic masterpiece.”
His creative partnership with Sheridan spans decades. Dillon first met him while struggling to break into Hollywood — via the advice of friend and actor Vera Farmiga — after getting sober. “I met Taylor, and he’s like, ‘It’s easy, use all the stuff you used in your band,’” Dillon says. Sheridan became a mentor, coaching him through roles on Durham County, Flashpoint and The Killing.
“Taylor was a great teacher and a great coach,” he says. “I was one of those students that stuck with him year after year, and we developed this rapport.” Over time, that mentor-student dynamic became a collaboration built on mutual respect. Dillon began writing his own stories, inspired by the specificity of his Canadian roots. “I create characters and worlds within my songs, and I wanted to explore where I’m from and things that happened to me that are super specific. Taylor got it. He had similar experiences growing up in Texas, so we just jelled. He trusts me, and I trust him.”
That led to a role in Sheridan’s hit series Yellowstone for Dillon, who also plays detective Ian Ferguson alongside Renner’s titular Mike McLusky in Mayor of Kingstown.
When the gritty series was finally greenlit, Dillon brought the production home. “We shot that first season in Canada,” he says proudly. “I got to go back to my hometown, and my mom and dad were still alive. It was important to me for them to see it all. It was during COVID, so people had jobs and were able to make consistent money. We used the penitentiary. And there’s Taylor walking down the streets of Kingston. Jeremy was looking at this prison going, ‘I just can’t believe this exists.’”
The experience, Dillon says, has been “profoundly satisfying, professionally and personally.”
As the show takes off again, so does Dillon’s other great passion: music. His band’s new album, BURN ALL THE SHIPS, dropped earlier this fall, and they’re heading out on tour this November, including a show in Toronto on Dec. 5 at Great Canadian Casino Resort.
“It’s all therapy,” Dillon says. “The band’s always been that way. It’s very therapeutic…and can inspire so many things.” The album features collaborations with Dallas Green and Metric’s Emily Haines.
Like his television work, his music is driven by collaboration and trust. “You find people who see something more in you than you may see in yourself sometimes,” he says. “They can help you fight through any kind of insecurity or questioning. That’s the through line between both things.”
