Pirates: Around 1984. Rick Reuschel or however you spell it was one of their top starters. He looked as athletic as the Stay-Puft marshmallow guy and I thought it was funny that a quality MLB starter could look so out of shape.
Steelers: Also around 1984. The year the 49ers won the Super Bowl over Miami and only lost one game all season. To Pittsburgh by a 20-17 margin, at least I think that was the score. Too bad there wasn't a SB rematch, but the Steelers were like 9-7 that year and got STOMPED by Miami in the playoffs, so that wasn't in the cards.
Penguins: Probably when Lemieux and Jagr led the team to championships. Due to living in rural Ohio and mostly just having the basic-ass 4, 6, 10, 28 out of Columbus, about all my hockey know-how came from Sports Illustrated and Sporting News, so I didn't really get into it as a kid.