Before becoming an actor, Playfair played hockey as a forward for the Merritt Centennials of the BCHL.
Beginning in 2014, he played Knox in the YTV series Some Assembly Required for all three seasons until the show was cancelled in 2016.
Playfair has often acted in roles involving hockey, due in part to his skating skills.
In 2016, Playfair started work on the hit Canadian show Letterkenny, as Reilly, one of the town's jocks.
This 'typecasting' has continued, as he joined the cast of The Mighty Ducks: Game Changers as Coach T.[4]