Today my guest on this podcast is actor Dylan Playfair. Dylan is best known for his work on Letterkenny, Haters Back Off, and Some Assembly Required. He plays Gil, son of Gaston, in the upcoming Descendants 2, which is out this summer. He’s also a film producer, and produced a movie called The Drop, about why young people don’t vote.


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Dylan Playfair is Canadian, and didn’t begin acting until the age of 19. He began in the film industry as a Production Assistant, or PA. Learning about the industry through working in it, he made his way into acting school, and began auditioning, landing a gig before he even completed school.

There are a ton of great takeaways from this conversation, including that his hockey training helped him land several different roles (special skills can give you a genuine edge in casting!), and that what can feel like failure can actually pave the way for success: he in fact auditioned for the role of Chad Charming in the first Descendants, and then Harry Hook in Descendants 2, before landing the role of Gil.

There are so many great quotes from this episode, but these are some of my favorites:

  • “Failure is not an option– it’s just a matter of how long it’s going to take.”
  • “Learning how to NOT do it can be just as valuable as learning how to do it.”
  • “Every failure is an opportunity to learn.”
  • “At the end of the day, an O-1 (Visa) isn’t going to be a roadblock. If they really want you, they’ll make it work.”
  • “If you’re good enough, they’ll see you.”
  • “Failures are necessary for success.”
  • “Of course (casting directors) want you! They need to fill those roles!”
  • “To find the ones who you share values with, and to make projects with those people… that’s fulfilling.”
  • “If you don’t book the role, book the room.”
  • “If you know in your heart that acting makes you happy– do it.”


Follow Dylan Playfair HERE (both verified accounts)

Twitter: @DylanPlayfair

Instagram: @DylanPlayfair1


No one can promise success in this business, but you can certainly raise your odds while saving a lot of time and money. If you’re ready to get some coaching on how to break into acting for film or TV, or are already down the road but stuck, book a consultation with me on my consultation page. For not much more than the price of an hour with an acting coach, you can get peace of mind, and a detailed action plan.