McKay was born in Saskatoon, Saskatchewan, Canada, and was raised in North Vancouver, British Columbia, Canada. He attended Handsworth Secondary School.[citation needed]
Along with close colleague, Danny Way, McKay was a member of the original Plan B skateboarding team, formed in 1991. Following the departure of Rick Howard, Mike Carroll, and Sean Sheffey, and the death of founder, Mike Ternasky, McKay and Way became the leaders of the brand.
Following the eventual dissolution of the original incarnation of Plan B, McKay subsequently joined the Girl skateboard team in 1995. McKay explained to Canadian skateboard magazine SBC, in 2011, "it just so happened that a lot of those guys on Girl were my friends; guys I've been around through my existence in skateboarding. I had just gotten on Girl around '98, when I was about 21. It was cool to be a part of one of the Girl/Chocolate videos ... To me, those videos are a big part of skateboarding, and it would've been rad to be around and take part in the skits and stuff that they do." McKay appeared in the Chocolate video, The Chocolate Tour, shortly after his arrival on the team and pre-existing footage was used for the part.

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