So many jump on the bandwagons with this kind of topic... I am not gonna say people are "wrong" but generally people judge stuff the wrong way.
Shawn, Taker and Flair get the accolade from a lot of people, but why? Is it cos they think they are amazing workers/performers or cos we are conditioned to think they are by the way WWE (or the NWA/WCW for Flair) portrayed them as such.
Shawn's early singles career was barely HOF worthy, littered with vacated titles, suspensions and mediocre performances...the stuff with Bret got him the heat he hadn't been able to generate although it is only really his 2nd career that gets him the plaudits, and again most of that is based more on how he was called "Icon, Showstopper, Mr. Wrestlemania" etc than him actually being the best. He could have awesome matches, or he could do what he did with Hogan...
Taker had an early boost from 3 big names and then spent the next 10 years beating far inferior people at Mania despite being clearly able to do far better in the ring, we got the standard Taker v Monster. It was telling he didn't get the title back for such a long time and when he did it was from Sid and it took Kane to really ignite him as a character AND worker. In the years since the quality of opponent has gone up but ultimately the match quality, while longer and more violent still revolves around his opponent rather than what Taker does, why else would he wrestle 3 (older) guys in 5 years?.
Flair has more claim as many considered him the best ever even before the NWA went to Turner and became WCW. In the plus column is also the recovery from the plane crash. Many forget that Flair was basically done in 1974, being told he'd never walk. That he turned it round to be considered in a poll of who the best ever would be is pretty inspirational. Sadly some of the tricks Flair learned to cope with that are also the reason why opinion on him is so divided. Some in the biz rate him the best, others think he was a shill who wrestled the same match for 25 years.
What all have is longevity and in Taker's case a carefully constructed mystique with the streak. The matches he and Shawn had were good, maybe near great but artificial, the closest Taker has to a 5 star match in my eyes is HIAC with Foley and I am sorry but one year between matches is not because "he is so good he doesn't have to" it's because he can't do more. Flair had his sheer number of titles but was hampered by his own foibles and to an extent the Mania moment with Hogan not happening. Had it done so, his career would have ended sooner, but with no doubt Flair was the best ever.
All 3 have stayed on too long, Shawn should really have retired rather than go through the Hogan debacle, Flair should have retired far earlier and Taker is now at the point where it's more "should he wrestle this year" rather than "will he", if the streak goes any longer with him so beat up, ending it would be worthless to whoever gets it.
So I am ruling those 3 out...
Bret, close but no - he was pretty bad on the mic for all his ring excellence and even then you can say he was a 5 move man same as Cena... he could do more, but rarely did unless it was with one of his pals like Davey. For all the innovation he did like the ringpost figure fours, a Bret Hart match was so formulaic that it became hard to watch by the end. Hogan, same thing, for a time in the 80's he could have been the best ever... but he hung on far too long and ruined his legacy by continuing to "hulk up" and put on the same damn match for 25 years.
Austin? Closer than any of them, but the neck injury robbed he and us of the Stone Cold we could have had (however successful he was) who was not only a hellraiser and icon but could work better than anyone on the roster. It left us a guy who again could do limited matches physically, what he did with what he had was amazing but it could have been so much better... same reads for Angle and Pillman.
So who do I count in?
Ricky Steamboat - Has to be top 3 if not the winner, for his whole career the man put on stellar performances all the time against literally every opponent. If there is a bad Steamboat match out there I am very surprised. Savage was closest to him but ultimately didn't have the variety of abilities that Steamboat had. Ricky had the best dropkick ever, his armdrags looked the best and he could even make a simple cross body look like the best top rope move ever.
Close to him is.... Chris Jericho
Yep, I am really putting Y2J above all those guys... blasphemy? Not really. look closely. You have a man who travelled the world to learn and hone his craft arguably the last "big star" who did. Calgary to Knoxville to Mexico to Japan to Philly and finally to the big time.
Jericho learned from everywhere he went and when he got to WCW there was a reason he was the main non NWO guy to be featured and was hanging with guys like Malenko who were considered genius. Once he got to the WWF/E he had the full package and the odd botch of the Lionsault aside was able to build his aura and abilities. He worked with guys like Eddie and he learned, he worked with Taker, Rock, Trips and still learned. He worked later with Cena, Christian, Orton and STILL learned. Even this last run where he lost constantly, he was still learning while also helping D-Bry, Punk and Ziggler become the talents they could be. That Vince wanted to make him the first Undisputed Champ has kinda been borne out by his contribution since, sure he comes and goes... but he regularly comes back and when he does he contributes, is never rusty and enhances the abilities of whoever he is in the ring with.
BUT... he ain't my winner...
My winner is -
Tom Billington AKA The Dynamite Kid
This is the man who truly revolutionized wrestling in the 80's, not Hogan, not Flair... Dynamite showed that not only can a smaller man hang with the monsters, but that he could become a marquee name that had the best match of the night...every night. Without Dynamite, there is no Bret Hart, no Shawn Michaels, No Chris Benoit, No Jericho, Rey, Eddie, Punk, Edge, Christian, Jeff Hardy, RVD and so on... All those guys got World titles and became main eventers cos Dynamite Kid paved the way, changed the world he was in and never got the glory himself. The only "bad" matches he had were when he was physically wrecked, prior to that back injury - he was simply untouchable and no one has measured up to him in impact or ability since. Over time a CM Punk might, if he has another gear. But Kid never had to "change up" or grow, he was the best from day 1 and that so many guys basically state they owe their careers to him to me, makes him the winner!