This period always gives me dissonance. It's my childhood preteen/early teen era, I started really playing and thus getting into everything hockey the very years the Wings started to win all those cups. So I have mostly an idyllic view of it, the quality of many games was good because the Wings were so good, but later on going back, getting into the old games collecting scene, the early and mid nineties was just better all up as far as I'm concerned looking at it now (don't get me wrong dead puck era is still way better than the powderpuff new NHL).
2003 Giguere's pads behind the trap in the playoffs was probably the first time I really looked at the product and thought, yeah this is absolute garbage lol
We didn't have cable for much of the time but the games were usually on both channel 50 and CBC which we picked up in Detroit (just needed to tweak that antenna a bit). I was pissed as more and more games went on Fox Sports Detroit in the early 2000s. Strader was leaving and Ken Daniels was starting, Mickey was a constant and it will absolutely suck when he retires. The voice of the Wings for me. Would also listen on the radio, loved Ken Kal's high pitched "SCORES" call. Paul Woods did color and had the funny Canadian hockey player way of talking which I enjoyed. National broadcast games obviously had Thorne/Clement and Cole/Neale which were awesome.
I remember pouring over the boxscore pages of the newspaper in the late nineties, where they also showed league leaders. Stats were a lot harder to get back then, and it was frustrating and got me into stats a lot at the time, but now with the easy availability of stats and our modern data centric zeitgeist, there's just way too much stats and most everyone always just points to stats talking hockey which I find annoying now.
Later when the internet came to our house (a bit late in 1999), I'd kill a bunch of time on the NHL website. It had some charm, and what I remember and miss the most from that is that after the games you could vote for three stars online. The ESPN website was really nicely done as one of the early Web 2.0 websites in the early 2000s, and I used that a lot. HF was apparently around but I didn't know about it until post lockout.
No HFBoards at that time meant that I and everyone I knew actually liked all the players on the team. I was somewhat shocked going on HF later and seeing the fans rip into so many of the players of their own team, like I wasn't exposed to this sort of stuff before. Sports radio and the beat writers of the Wings at the time I got into it were handling the team with baby gloves, I missed the really juicy part of the mid nineties I guess. There was a bit of drama with Fedorov of course, but I really didn't care about the business aspect of it so much, I just loved having him come back to the team late during the 1997-1998 season and was bummed when he left after 2002-2003. I first understood free agency with regards to Mike Vernon, when I asked a friend if he was traded and he responded "he traded himself".
I remember Lemieux's comeback and I didn't like him much then. I knew who he was from the hockey cards and a bit from his retirement season but he seemed to rack up so many points despite not really playing at an impressive level commensurate with the stats. Now having watched real prime Lemieux from the early nineties, I think he's probably the best player I've seen, definitely best player in terms of finesse skills.
When the Wings started retooling and making splashes in free agency, I was always excited. We'd always look forward to a marquee name joining the Wings in the spring or after the playoffs. Murphy, Chelios, Verbeek, Clark, Hasek, Hull, Robitaille, Joseph, Hatcher, and so on. The most interesting one was after the 2002 cup, when the Avs got Kariya and Selanne, and so the Wings loaded up with Hatcher. Of course, there wasn't another meeting in the playoffs, and the new additions didn't make nearly as much of a splash as their names would indicate. None of this cap garbage back then, but it seems that a subset of fans really geek out on this stuff now so that's another way to get engagement.
After the Wings, I mostly followed the Avs, then the Stars as the obvious big threats. The Blues were getting kinda good too in the division. Joe Thornton on Boston was like the first player beyond that that I tried to really follow for a while until the lockout.
I got into the drafts in the early 2000s (even though I had stopped playing, I was still buds with and had played with guys who continued on into the NAHL, including one who made it to major juniors with Plymouth (another eventually played NCAA for UConn), and they were really into that stuff). The anecdote that sums up that period the best is my bud mocking the scouting mantra of the time "you can't teach size" (poor guy maxed out at 5'11" lol).
Eric Staal was the first junior player I remember being really interested in, and then as the lockout loomed I started to hear about Crosby for the first time. I have no idea if this story is true or not, just a friend of a friend narration, so take it for what it's worth, but I heard that Crosby's work ethic was so high, that girls would come up to him offering themselves to him, and he'd be like "mmm... after practice" lol (my friend would say this in an extremely dorky voice lol)
Easton was big in the stick/skates thing (I'm talking even pre Synergy), I always wanted an Easton stick from that period but never got my hands on one. Lots more brands at that time, I rocked a Koho for a bit, and the last stick I had before quitting playing (things were starting to get real expensive in the early 2000s) was a Nike aluminium which I thought was the coolest thing ever.
Roller/street hockey was everywhere back then. I actually enjoyed it more than ice. Started off with those cheap $20 buck blades from like Kmart but eventually picked up a pair of Missions which were the shit back then if you remember. Us neighborhood kids would always talk about bearings and stuff that we didn't really know about. We'd play as Wings vs Avs of course, and it would suck when your group was the Avs, I remember when I first started playing, one game, I was told I was Forsberg and I was like "who the hell is this guy? I wanna be Yzerman or Fedorov" and they were like "no he's really good" lol
Since I was getting into the whole hockey thing I also got into hockey cards, and since there was a glut of the early nineties produced cards, I had a lot of them years later, and I'd try to figure out the anachronisms of the high point totals and projections from back then into the current game. That along with the contempraneous complaints about the quality of hockey at the time made it so I never thought I was actually in the golden age of hockey at the moment, more like it had just passed, which is interesting. I was also incredibly psyched for the new NHL as it entered, but almost instantly turned off by the penalty fest and wussification that I saw happening. It's never been softer now as far back as I can remember... sigh
Late into the nineties the NHL started tweaking crap to increase scoring and there was a lot of media discussion around the lower point totals of the stars and why that was. I even did an article for my school paper in journalism class on this topic. It was my first real "research" into the evolution of hockey, unlike a lot of my other crap I wrote for the paper in that class, I really gave an effort for this assignment.
Yzerman was climbing up the all time scoring leaderboards at the time, which somewhat got me into the history of hockey, wondering who are all these players are. Same with Roy passing Sawchuk's win record which was a huge deal. Also the appearances of guys like Howe and Lindsay from Detroit's original six era during the late nineties success.
I remember Marty Turco (I think) was the first goalie in like forever/since it was tracked, to post a sub 2.00 GAA and it was a big deal. Barry Melrose was always talking about how save percentage was the best goalie stat, because back then, people seemed more into wins and GAA.
If you asked me back then who the best player was, it was obviously Gretzky, because of his "greatness" popular acclaim, even though the player that seemed the "best" on the ice watching would obviously be Lindros, and Gretzky honestly wouldn't register as close to the best at that time.
Smallworld online fantasy hockey was big late in the early 2000s, and that was my first exposure to it (never did the degenerate gambling pools pre internet thankfully... the amount of gambling promotion nowadays is yet another nail in the coffin of NHL hockey today). I remember I made a team called the "Nutty Canucks" where I spent most my budget on Naslund and Bertuzzi and Niclas Havelid did good for me as a league minimum defenseman lol
In terms of video games NHL 2000 was the thing man (also had NHL 99 which had the best intro even though its successor leapfrogged it). Never saw too much need to get the later releases. I still really like the way that you could see the entire roster 4 lines/3 D pairings on one screen. I did try some of the later games like 2009/2012/2013 and it was just like bleh with the user interface among other things.
Despite hockey's zenith moment probably happening earlier in the nineties, the media culture was still very strong around the late nineties, so many choices for hockey magazines and cards and equipment brands and all that. It seems far more constricted today even with the proliferation of the internet, because even if there are far more voices, the big ones have all seemed to consolidate.