Before making the NHL, Playfair played for the Fort Saskatchewan Traders located just north of Edmonton. He played for the Edmonton Oilers and Chicago Blackhawks over the course of his career. His older brother Larry Playfair shares a lot of the same characteristics - both were drafted in the first round of the NHL Entry Draft (Larry in 1978 and Jim in 1982), and both played junior hockey for the Portland Winter Hawks of the Western Hockey League. However, Larry played in 688 career NHL games; Jim for 21.