I'm through Rumble '97 and I was wondering when Raw went to 2 hours because this was very much in the Monday Night Wars era. Royal Rumble Raw at Skydome appears to be the first 2-hour episode of Raw. They follow up with a 2-hour show after 'In Your House'.
I've been debating over watching WWF, WCW and ECW chronologically and I think I'm where I want to start doing it.
I remember the Shawn "losing his smile" angle but forgot how and when it went down. On a Thursday Raw right before 'In Your House'. It made that Final Four match with Austin-Undertaker-Bret-Vader for the title.
That '97 Rumble was a strange match with Austin winning after being eliminated but it furthered the storyline with Austin and Bret and it lead to that 4-way match. It's long been a WWF/E move to have a goofy ending to a match but it's all to set up a bigger match down the road.
I can't say it enough when I tell people to not watch the old weekly shows.
I've been following along with Alvarez's show (with Vinny and Craig), watching shows from 19 years ago each week, and it really is terrible. And not terrible in a good way, terrible in a terrible way. Wrestling was big when it was big despite it's self.
At least 1997 WWF is really good, mostly the main event guys as the undercard is full of crap, but 1998 is really bad. Austin is great, but you're into the Russo era of trash. The bits with Austin are still great, but hardly anything else is worth watching. Watching Rock over these years is also great, as he really takes off from trash to Rock.
WCW is just a complete mess of a show, and never gets better. There are random good matches, but there is nothing to actually watch for outside that. You don't have an Austin or Rock to watch, you have a stale NWO to endure. Goldberg is around, but he isn't anything like Austin. He doesn't have 'must watch' segments, just a squash match. When he's actually on the show. Oh, and Nitro is three hours of trash each week that make current Raw a breeze
ECW I never watched as it was never my thing.
But If you really do want to go back to watch everything, I recommend skipping a lot of each show. Most of the show really. It's not worth the suffering.
I will, however, recommend watching late 80s WCW. That stuff is awesome.