Dylan Playfair was born in Fort St. James, British Columbia, the son of Roxanne, an entrepreneur and stay at home mother, and Jim Playfair, a former NHL player and coach. He has two younger brothers, Jackson and Austyn. All three boys grew up playing hockey and traveling around the United States and Canada as their father coached various minor league teams on his way to the NHL.

Playfair's diverse body of work includes the critically acclaimed comedy series Letterkenny, Disneys' Descendants 2, and Netflix's Haters Back Off and Travlers. Roles ranging from a young man dealing with extreme adversity in "Never Steady Never Still" to producing and staring in political documentaries centered on youth voter apathy (The Drop). Playfair began his career in film at the age of 19 after playing Jr. A Hockey in Canada. A graduate of Vancouver Acting school, he has also studied in Los Angeles during his career.