I was born in Montreal, Canada, back in 1973, and have fond, although faint, memories of watching the Montreal Canadiens (aka The Habs) win the Stanley Cup year after year in the late 70s. Well, my memories are really about being with my father’s friends and lots of yelling, cheering, and high-fiving, and some vague mental imagery of guys in red and white (and a little blue) skating around the ice.
My real transition into a bigtime hockey fan happened in 1993, while I was a student at Carnegie Mellon University, which is in Pittsburgh, PA. Back in the early 90s, the Pittsburgh Penguins dominated hockey, and everyone picked them to three-peat the Cup victory in 93. But they got eliminated in the second round by the Islanders, and I happened to watch Montreal beat Buffalo in four games straight (three in overtime).
By the third round, I got a little excited, and some of my classmates started watching with me, and we watched Les Canadiens dominate New York, although there were a couple of nail-biting overtime moments (2 more games went to overtime). But by now, despite hockey being fairly dead to the city, I was completely enthralled.