For many, this is probably a really hard question to answer. Depending on how long you've followed this team, there could be 10-20 moments that you could choose from. There's Steve Yzerman's double OT goal against the St. Louis Blues. You could pick Darren McCarty's amazing Cup winning goal in the 1997 Final. Who can forget the moment Yzerman handed the Stanley Cup to Vladdy in 1998? If you're Tyler, you'd pick Nicklas Lidstrom's goal from center ice during the first round against the Canucks in 2002. There's just so many awesome highlights to choose from.
I'm sticking with the 2002 season, but to me the conference finals might be the greatest highlight. After Patrick Roy pulled the Statue of Liberty move in Game 6 and gave the Wings a win, it all came down to Game 7. The two best teams of the late 90's/early 2000s were set to settle their rivalry in a winner-take-all battle to reach the Final (and we all know whomever won Game 7 was going to beat the Hurricanes).
I've never been more nervous and excited for a game than I was for Game 7 of the 2002 Western Conference Finals. The team I love the most against the team I hated the most. Good versus Evil. The Red Wings were built as a power house that season and it was Stanley Cup or failure. It was all on the line and the Red Wings showed the world that they play second fiddle to no one. They promptly scored on Patrick Roy only two minutes into the game...and then they scored again...and again...and again...and again...and again...and again. It was the perfect ending to the rivalry between these two teams. The Wings went on to win the Cup that year and officially won the war against Colorado in the history books.
Let's Go Red Wings.