Hugh Dillon Discusses How ‘Mayor of Kingstown’ Made It To Season 2

The actor and co-creator of the show sits down with FilmSpeak to talk about the inspiration for the show, and how he went from a college-town to working with Taylor Sheridan.

In all fairness, there are plenty of modern day celebrities that are looking for that next hyphen. They want to be a singer/actor, or a writer/director. Long gone are the days where most celebrities were content with merely being a well established performer, and there’s nothing wrong with that at all, yet in some cases, you can’t but question that extra title. Are they really an Executive Producer on that show in all capacities, or was that merely the result of an excellent agent to gain a little more pull on their show.

Then there are those who simply evolve. Those who earn it. Those whose natural uncanny artistic ability cannot simply be contained or defined by one title. Those like Hugh Dillon. 

For years Dillon was the frontman for the Kingston, Ontario born alt-rock band, Headstones. For a suburban teenager growing up in the Toronto area, Dillon was the frontman of their late high school life as they burgeoned into adulthood - a great reminder that Canada is a great place for some good natured angst, edge and artistic expression. 

As Dillon reveals, growing up in Kingston was all the reminder he needed in regards to artistic expression. He can recall a time growing up where some of Canada’s greatest rock stars all grew up together. “I go right back to the high school. It's me, Gord Downie and Dave Usher. We had great teachers, and it was just a great time to be at school in the early 80s.” Dillon recalls. Dave Usher was another Kingston Collegiate and Vocational Institute alum who went on to major musical success in the 90s with Moist, and his eventual solo career, and Gord Downie was the lead singer for arguably the greatest rock band to ever come out of Canada, The Tragically Hip. Gord was a close personal friend of Hugh’s from a very early age, through their years of musical success, up until the time Downie lost his battle to cancer. 

“He is responsible for me being here. If it wasn't for him, I wouldn't have gotten a record deal. He went to bat for me.” Dillon, humbly admits he owes so much to Downie, but it goes further than merely his success within the music business. “All we talked about back then was stories, and characters, and songs, and artists. We were dreamers and uncompromising in those dreams. It was just an amazing time to be inundated with art music.”

Many artists share the same dream it would seem, that of not being confined within one art. All those aforementioned hyphens come into play eventually for most professional artists, and when Dillon made the switch to acting, he met another kindred dreamer. “When I met Taylor Sheridan years later, it was the same thing,” Dillon adds. Apparently television’s newest golden god, Taylor Sheridan, the man behind the juggernaut Yellowstone, Mayor of Kingstown and Tulsa King fits the mould of an uncompromising dreamer as well. “I knew Taylor before he became ‘Taylor Sheridan’, he was my acting coach. 

That early working relationship with Sheridan led to the two ‘dreamers’ to meet professionally time and time again, but it was during the time Sheridan was coaching Dillon, as the actor was starring in the cop-drama Flashpoint, they came up with Kingstown. The two had extensive conversations about the world they wanted to build, and it eventually came full circle back to Dillon’s hometown. Kingston, aside from being a ‘college town’, is predominantly known as Canada’s prison town, housing as many as nine penitentiaries, and the country’s only federal institution. It was the perfect backdrop to a gritty crime-drama about gangs and prison life in a steel-town simply trying to hang on.  

It wasn’t an immediate jump from their early days as coach and acting student to mega successful creator and established actor, however. After Sheridan cut his teeth in the writing world, penning Sicario and the Oscar nominated Hell or High Water, he cast Dillon in his sophomore directorial effort, Wind River (coincidentally also starting Sheridan’s working relationship with Mayor of Kingstown star, Jeremy Renner). Eventually Dillon would have a featured role in the juggernaut Yellowstone as Sheridan solidified himself as television’s newest Midas. Dillon’s character was eventually killed off in order to free up some time for his role in Kingstown. While production was originally filmed in the real Kingston, they have now shifted to Pittsburgh for season two, however Dillon is ecstatic that he was able to bring the show to life in the very town that inspired him. “We were lucky to get to Kingston and be able to use that penitentiary and for me, it was profoundly satisfying to bring that story back to Kingston and bring those jobs in in the middle of a pandemic.”

Dillon, ever the humble Canadian-boy, recognizes that while he has certainly taken the next step in his career as co-creator of a Sheridan-piloted show, that a lot of it was perhaps simple good fortune. “Taylor hired me to be in Wind River [where] I met [Jeremy] Renner” Dillon recalls. When the trio were able to create that film, it clearly inspired all of them to work together again, Dillon admitting that Renner was always his first choice for the lead of Kingstown. Yet good luck will only take you so far, and when coupled with the two creator’s work ethic, it seemed as if Kingstown couldn’t really fail. Dillon seemingly always had faith in his friend and creative-partner, adding “Taylor is a world class creator. [I always knew] he can get us where we need to go, but we've been very lucky every step of the way. It's just been an incredible ride.”

Mayor of Kingstown’ season 2 is streaming now on Paramount+


Check out the full interview with Hugh Dillon, below: