Holy shit - we're talking about hypothetical matches which don't even exist. Well, hypothetical matches don't exist by their very nature, but you get my point. We've (and by that, I mean "you've") finally gone off the deep end.
But again, we're talking about speculation. Undertaker winning ONE ladder match means nothing, especially going up against a man that has one numerous of them.
I appreciate your point, to a degree, but the example is a poor one. Rey Mysterio isn't particularly experienced in ladder matches. According to Online World of Wrestling anyway. He's had exactly one singles ladder match in his career; against Eddie Guerrero. His son was on the line and everything.
Now, enough about fucking Rey Mystero in a ladder match with The Undertaker. I'm not talking any more about hypothetical matches unless I absolutely have to.
Speaking of which, who would win in a match between Bret Hart and CM Punk? Better yet, what if it was an object on a pole match? Shit, I can top that - what if it was in WCW? That'd be pretty crazy. "What would happen if CM Punk and Bret Hart had a metal object on a pole match in WCW?" - one of life's great questions.
I've not read most of this thread, but I'm going to blindly assume that it consisted of both sets of fans calling the other fans' wrestler overrated. CM Punk is an internet darling and people only love him because he came through the indies and got politicked out of a title by The Undertaker, but Bret Hart is an overachieving midcarder who was fortunate to be in the spot he was in and got jostled out as soon as the actually worthy came in, etc. etc. Why let a wacky gimmick get in the way of such fun?
Me, I've never been a fan of rose-tinted goggles. I can, however, say that I've watched Bret Hart matches on DVD, and say that he was pretty good. Shit, he was pretty great. I changed the adjective after consideration - that's how passionate I am about this. As good as WWE marketing with their video packages and best of collections would have me believe? Well, how am I to know that?
At the end of the day, Hart was vulnerable. He had great matches, but he lost. Could he have conceivably lost to a CM Punk in his prime, one who's not lost to anyone clean? Sure. And I think it would be a watershed moment if he actually does that.
By the way, Punk would fucking clean up in a ladder match. Just saying.