Over the 12 series of Letterkenny, Dylan Playfair played Reilly alongside Andrew Herr as Jonesy, with the TV show being nominated for and winning numerous awards including Best Ensemble Performance in a Comedy Series at the 2024 Canadian Screen Awards, and Dylan also toured across North America in the live production – Letterkenny Live!. Dylan played Larry Lampshade in Buddy Games: Spring Awakening, Cameron Betts in Dangerous Game: The Legacy Murders, and he played Dean Hunter in Odd Man Rush. Across both series of The Mighty Ducks: Game Changers, Dylan played Coach T, and amongst his further screen work, he played Gil in Disney’s Descendants 2 and 3 (for which he was directed by Kenny Ortega) and had his first regular role on TV playing Knox in teen sitcom Some Assembly Required. Alongside his acting career, Dylan is also a producer, most recently being the executive producer on short film Dragon Fruit. Future work for Dylan includes the upcoming thriller Influencers, comedy Above The Live and Mike & Nick & Nick & Alice. We spoke to Dylan about his time as Reilly in Letterkenny, playing Coach T in The Mighty Ducks: Game Changers and filming as Gil in Descendants 2 and 3.

Across all episodes of the comedy series Letterkenny, you played Reilly, how would you describe the character and what was it like developing the role over the 12 series?

Reilly became an extension of myself, when you have the opportunity to play a character that long, in a show that’s loved by so many the way Letterkenny is, it becomes a part of you. I was making a hilarious, intelligent, critically acclaimed show with my closest friends. What Letterkenny did was show me how it feels to capture lightning in a bottle. It’s given me a strong desire to do it again and create more things with the people involved in that series and make more series like it.

What are some of your favourite highlights from your time filming for Letterkenny and what do you miss most about being on set of the show?

The time spent with the people was always the highlight of filming Letterkenny. I remember beach days with the cast when we would film in the summer, and freezing our asses off in the middle of February shooting in the snow. Oftentimes we would be laughing so hard in rehearsals that we couldn’t breathe… That’s why we rehearsed, to get the giggles out. That cast was very tight and we had a lot of fun together. That’s what I remember and what I will miss.

What was it like working alongside the rest of the cast, which included Andrew Herr as Jonesy, and touring with your fellow cast members for the Letterkenny Live! productions?

Andrew and I have a chemistry that’s difficult to replicate. There’s almost a telekinetic communication happening when we rehearse, when we deliver dialogue and even when we hang out off set. He feels a lot more like a brother than a co-worker and he is one of my closest friends. As far as touring is concerned, we had the chance to live like rock stars, travelling all across North America, sharing Letterkenny live with fans from around the world, some came from very far away places to see us perform (what’s up, Australia!). It’s an experience that feels as if it went by in a flash and one I will never forget.

How was it seeing the fan response to Letterkenny and having the show be nominated for and win numerous awards, such as winning Best Ensemble Performance in a Comedy Series at the 2024 Canadian Screen Awards?

It’s been on my vision board for a long time (to win a CSA) so to finally have one in my home not just with my name on it but alongside the names of some of the greatest performers I know is a real treat. Letterkenny is very near and dear to my heart and it’s very rewarding to know fans and peers have responded well to it.

Can you tell us about filming as Larry Lampshade in Buddy Games: Spring Awakening and Cameron Betts in Dangerous Game: The Legacy Murders?

Larry Lampshade was a super fun character I got to play working alongside Josh Duhamel, Nick Swardson, Kevin Dillon, Dan Bakkedahl and several other very talented actors and filmmakers. It was lots of fun getting to cut loose with so many performers I look up to. That set had some real Letterkenny vibes in terms of all the fun we had.

Dangerous Game: The Legacy Murders was another opportunity to work with some really talented folks including Oscar winner Jon Voight and Canadian comic genius Will Sasso and the insanely talented Jonathan Rhys Meyers.

What was it like playing Coach T in The Mighty Ducks: Game Changers for Disney+, and reprising your role in Series 2?

Like so many kids in my generation, I grew up watching The Mighty Ducks films so when I had the opportunity to meet Steve Brill to discuss the role of Coach T it truly was a full circle moment. I had heard he was a fan of Letterkenny and he had heard I was a fan of The Mighty Ducks. We met and ended up talking hockey and film for several hours, he’s a great dude and the hockey world owes him a lot in terms of bringing so many new fans to the game as well as an NHL expansion team.

How was it being involved with the feature film Odd Man Rush as Dean Hunter, which was released on Hulu in 2020?

It was great, hockey is in my DNA and Bill Keenan, the writer also grew up as a big fan of The Mighty Ducks so we had a lot in common. Filming in New York and Colgate University was a really cool experience. Doug Dearth, our director, and his wife Beth are some of the kindest people on Earth and I’ve remained close to hockey and film royalty Howard and Karen Baldwin as well as Todd and Grant Slater. There was a lot of family on that set and it was very much felt on set.

You played Gil in Descendants 2 and 3, can you say about some of your stand-out memories from working on the films?

The preparation the cast put into all the Descendants films is something I will never forget. Five days a week for two months we rehearsed. We went through the dances, the songs, the choreography, the stunts, we trained and became a team with a shared goal. It was a process I will never forget. Cameron Boyce was one of the kindest, most talented people I’ve ever worked with and I remember him staying long after wrap with me so we could rehearse our sword fight sequences and dance numbers. He was a natural with such an inviting, generous and kind energy. It’s wild how close a cast becomes during the process of making a film and Descendants is no different, we became a family and shared in the creation of something very special.

What was Gil like to play and what was it like being directed by Kenny Ortega for a hugely-popular Disney musical film franchise?

Kenny Ortega is a legend for a reason, he creates magic wherever he goes and whatever project he brings to life is sure to become something memorable. There was always something inspiring and exciting coming out of Kenny. You wanted to bring your best to set every day because seeing him respond positively was a tried and tested mark of approval, not just for him but for the fans. He knows what works and trusting your director to ensure the best version of your performance is going to be showcased is an incredible feeling. Gil is fun, silly, big-hearted and a treat to embody. Every character is special, Gil’s impact on me has been profound. My love and appreciation for musical theatre has grown in ways I couldn’t have imagined before Descendants.

How did you find the experience playing Knox in the teen sitcom Some Assembly Required for your first regular role on TV?

Like Gil, the character was just so much fun to embody. Having a live studio audience in front of you, responding to the material is something that’s impossible to replicate. We had a working roller coaster on set, we were all early in our careers and we all came to work to make people laugh. It was a dream role to land early in my career and it shaped the way I look at how good sets are run. We had fun, we worked hard and we created something that people feel a deep connection to today. One of my favourite things about going to fan conventions is meeting folks who watched Some Assembly Required on YTV when they were in school and now they’re driving cars, going to college, etc. etc. when they come up and tell me how Some Assembly Required was a part of their childhood experience it really warms my heart.

Where does your love of acting come from and how did you get into it?

I’ve always loved watching movies and TV, ever since I was a little kid. In the summers, we would stay at our family cottage on the lake with no cable, no internet, just a TV and VHS player, we would rent movies and whole seasons of The Simpsons and watch them on repeat all summer long. I used to impersonate Steve Irwin – The Crocodile Hunter and many of Mike Myers’ characters from the Austin Powers films. I knew from a young age that was something I wanted to do.

We understand you also work as a producer, most recently executive producing the short film Dragon Fruit, can you tell us about this side of your work and what do you enjoy most about producing?

I think many actors turn to producing at some point in their career as a means of holding some agency over your career. As actors we are often waiting for an opportunity to come, as producers we are the ones creating that opportunity. That’s what I love about producing, creating the opportunities.

Do you have any favourite films and TV shows to watch?

Right now we’re watching Severance… the cliffhangers are driving me up the wall at this point but we’re hopelessly hooked on the show. Anything with Chris Farley is timeless. All of Pete Berg’s projects are incredible. The Trailer Park Boys are groundbreaking. I have a wide ‘taste’ in film and TV… I also love a good history documentary.

How do you like to spend your free time?

Luckily I love what I do so my work time, in some ways, feels like my free time… even though it can be hectic. When I’m not acting, producing, or preparing for a project, I love to play hockey, travel and spend time with my wife Jen and dog Teddy.

What are you hoping this year brings for your career, and do you have any projects coming up that you can talk about?

I want to continue working on projects with talented people who have a shared vision. Film and TV is about building a team and working together to achieve a goal. I’m very excited about a few projects that will be coming out in the next year or so. Influencers – a thriller we filmed in Bali last summer with my close friend and filmmaker Kurtis David Harder where I play a social media Influencer caught in the web of a serial killer. Mike & Nick & Nick & Alice with Vince Vaughn and James Marsden was filmed in the fall where I had the opportunity to work (act) with another group of genius filmmakers including BenDavid Grabinski and, of course, the aforementioned James and Vince… Marsden and Vaughn… So that was cool. Also look out for the release of Above The Line, a heist comedy by Jeffrey Scott Collins and Jono Matt with Cedric The Entertainer, Sophia Ali, Jackson Pace, Reno Wilson, and Jamie Lee to name a few of the very talented folks involved in that film. I’m always looking for the next project which keeps me excited and engaged. Thanks for taking the time to chat and I look forward to our next interview.

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