Stern was born in Sainte-Agathe-des-Monts, Quebec, Canada, and is Jewish. He played for 3 years in the QMJHL with the Longueuil Chevaliers, establishing himself as an enforcer with a scoring touch. His strong play led him to be drafted by the Vancouver Canucks in the 4th round, 70th overall, in the 1986 NHL Entry Draft.
After being drafted by the Canucks, Stern returned to the Chevaliers for one final year before turning pro for the 1987–88 season. That year he played the majority of the season with the Flint Spirits of the IHL, appearing in 55 games and registering 294 Penalty Minutes. He also made his debut with the Canucks, playing in 15 games. The next three years saw Stern bounce between the Canucks and their minor league affiliate Milwaukee Admirals.
At the trade deadline near the end of the 1990–1991 season Stern was traded from the Canucks to the Calgary Flames in a deal for Dana Murzyn. In Calgary, Stern established himself as a full-time NHLer, and earned a reputation as a feared fighter amongst fellow NHL heavyweights at six feet and more than 200 pounds. Stern played the majority of his NHL career with the Flames, spending 6 years with the team and enjoying his best success in the NHL. He set career highs with 13 goals in the 1991–92 campaign, and with 29 points in 1993–94.

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