The Red Wings 97/98 Cup teams were a huge part of my childhood, and I have some personal favorites from back then I figured I'd share:
1997 Cup run - I was 10, and at that point hockey was never a big thing in my house. I'm assuming my Dad was drawn in by the sensationalism of the potential WCF with the Avs, because the first game I ever watched and ever witnessed my Dad watch was during the 2nd round against the Ducks. I watched Sergei Fedorov, with his crazy Nike skates and gloves and weird mullety hair that wasn't even remotely damp, make a rush down the ice and I was HOOKED. I made a point to watch every game for the rest of the playoffs and my life became Red Wings everything after that. One thing I'll never forget was the fanfare during the Finals. Like every kid that grew up in Troy during the 90's, I played organized youth soccer. That year, the end of the season "tournament" was held the same day as game 4 of the Finals in the morning and afternoon. The amount of cars in the parking lot adorned with Red Wings flags, and minivans with brooms sticking up out of their 3rd row windows was INCREDIBLE.
My first game at the Joe - 2/25/98 vs. the Kings. Sat probably less than ten rows from the very back wall behind the Wings goal in the 1st period and watched Osgood let in a softy from Josef Stumpel something like 13 seconds into the game... Then missed Brent Gilchrist tie it up while in the bathroom to start the 3rd... The 1-1 game was pretty boring for me as a kid. At the time, Sergei Fedorov was my favorite player. Being 10 and less than a year into my Red Wings fandom, I didn't really know or understand the details of his absence that season. I just remember going on my Dads computer before leaving for the game and making a sign that said something about wanting Fedorov to come back. Needless to say, I felt pretty awesome the next day when I heard on the WJR Mitch Albom show that my Mom listened to EVERY evening that Fedorov was coming back.
One of my worst from back then:
Uwe Krupp - Hindsight's 20/20, but that signing not working out was hugely disappointing to me as a kid. At that time, I didn't have unlimited access to the web, so my initial Red Wings/hockey news/info came from watching their games, looking at stats on my PC versions of NHL96 or NHL Powerplay 98, overhearing my Mom's radio playing the Mitch Albom show, or my Mom relaying what she heard from Mitch Albom to me. I would then usually hunt down that days Oakland Press to confirm. Anyway, I remember her telling me to come listen to the radio one day, because they were interviewing some "huge guy named OOVEE the Red Wings signed". I was always diligent in adding the newest (and existing within the game) Red Wings to the team on NHL PP 98 and then playing a whole bunch of games (usually on "easy" lol) to see how the team looked winning games by double digit margins with the newest player(s). Then, my Dad got me the PC version of NHL99, which gave me a huge (no pun intended) appreciation for Krupp. For those unfamiliar, NHL99's graphics or whatever greatly exaggerated height and weight, to the point where a 6'6" 235lb Krupp looked like a giant Michelin Man wearing a Red Wings jersey. In fact, he appeared almost as big as my created player version of myself, which I made the max 6'10" 250lb and with the biggest beard available. In that game, open ice checks made an extremely over exaggerated crashing noise and caused opposing players to do a backflip, which would trigger a recording of Jim Hughson saying "A TRUCK HIT HIM". They looked pretty cool to an 11 year old me delivering them with my massive created player and Uwe Krupp. Unfortunately, the games I saw that year with Krupp didn't seem to feature those kind of hits, and other than being tall, he certainly wasn't as inflated looking as he was in the game. I was bummed when he got hurt and then suspended from the team, but I sure had a lot of fun on NHL99 when Holland went out and got Chelios, Samuelsson, Clark and Ranford later that year.
Past childhood, I'd say my favorite was the entire 2008 season. It was entertaining from day one. The Igor Grigorenko saga in camp, Aaron Downey making the team and providing some fisticuffs and pounding LaPerriere after he put a dirty hit on Lidstrom, watching peak Zetterberg and Datsyuk surrounded by a whole bunch of young guys quickly improving and settling into their roles, McCarty's return, Dallas Drake throwing around his body in the playoffs like he had absolutely zero regard for his physical well being, watching the often maligned Osgood help lead them to a Cup, and then attending the Cup parade and hearing boo's for Kwame Kilpatrick loud enough to drown out horns from passing boats on the Detroit River. Priceless.