It's hard to say because nothing he did in his career touched his mid 97-98 run mic wise. I hate the word swag but during that run HBK's swag was another level. Work wise it was always there but I might have to give the edge in ring to the 2000's just because IMO he consistently faced better quality wrestlers, especially the first half of the 2000's.
It's really hard to say but I may have to give a slight edge to the 90's just based off the strength of his 97-98 run. But at the end of the day we were all blessed and made better men being able to watch the GOAT wrestle.
If you're talking strictly matches, then I'd go with the 2000 run. He was there for 8 years and got to work with much better talent than he had in the 90s.
But from a character POV, Shawn from the 90s was better. He was a better athlete as well, but he didn't have the luxury of working with as many good workers then as he did in the 2000 run.
Personality wise, definitely 90s.... with the Hogan feud showing a brief resurrection of Heel Shawn.
Ring work...eh, toss up. I'd lean towards 2000s, not because he was any more talented but because he had better opponents.
Angle, HHH, Undertaker, Jericho
Taker and him were great in the 90s too. Bret and him had potential, but their two matches are overrated I think. His back was shot w/ Austin. The rest were meh at best, Kama, Davey Boy, Sid, Diesel etc etc..
but i prefer his 90s run..dude was in prime ringwise and carried average workers to near classics..only he can actually make me rewatch a match with jeff jarrett and be like ..97-98 dude was a walking heat machine
the 2000s he was still competent in the ring but the personality part was missing..he was dull (except against hogan)
His character in the Late 90's was better overall, but He had the best matches in the 2000's. From 2003 on he was delivering at least 3-4 different classics or near-classics each year until he retired.
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