The son of former NHL coach and player Jim Playfair, Dylan grew up traveling around Canada and the U.S. for hockey. He played Junior A hockey 2010–11 with the Merritt Centennials (BCHL). As left-winger, he scored no goals, had one assist and spent “a lot of time in the penalty box” (56 PIMs over 42 games) (Vancouver Sun).
A graduate of Vancouver Acting School, he began his acting career around 2012. He played Marty Howe in the TV movie Mr. Hockey: The Gordie Howe Story, which also featured Andrew Herr ("Jonesy") as Mark Howe. He had a recurring role as Owen in Haters Back Off! and as Knox in Some Assembly Required, for which he has earned Leo nominations and Joey awards.
He produced and appeared in The Drop: Why Young People Don’t Vote, a documentary on political apathy, for which he won the best producer award at the 16th annual Beverly Hills Film Festival.
In January 2019 he announced his engagement to actress and fellow British Columbian Jen Araki.