>>5263309Since there wasn't as much TV back in the Hulkamania Era, that's easy to just breeze through. Just watch Manias, SummerSlams, and Rumbles from 1987-1991.
1992 is a fun watch for all 4 PPVs there.
New Generation Era is pretty skippable. Just look for isolated matches there and watch WrestleMania 10.
As we get into the Monday Night Wars, it's tough to tell you what to watch. Summer of '96 WCW and up until Starrcade '96 is all fun.
1997 is a lot of stalling until Starrcade '97, but 1997 WWF is really fun. So is '98 and a lot of 1999.
Beyond that, you're on your own because once Vince goes public and HHH and Stephanie act like the future owners of WWE, wrestling begins to stagnate. Manias are still fun overall until you get to current era, though.