Nothing controversial at all. I'm a huge San Francisco Giants fan who was born in 1980 -- no matter what he does, there is a part of me that thinks "Pablo Sandoval is no Matt Williams!" Brandon Belt can have a breakout season, but he'll still be dog shit compared to Wil Clark (he might move up to being even with JT Snow if he's lucky). And when I was a kid, my dad used to always say that 'The Thrill' was no 'Baby Bull' or 'Stretch'. Previous experiences get in there deep and are hard to distance yourself from.
My two best buds are serious wrestling fans (they have been watching it every week from childhood into their early-mid 30s), but getting them to look at wrestling outside of what they grew up watching is next to impossible. Whether it was showing them American Dragon matches 6-7 years ago, or making them a 3-disc comp of my favorite Southern matches from the 80s (which neither can be bothered to even put into the DVD player!), they just aren't interested in anything outside of their comfort zone. For the Flair vs. Bret argument, they are familiar with both and would probably vote along their favorite promotion's lines, but they would both put Bret and Flair over someone like Lawler and laugh in your face for even bringing him up. Neither would go online and get into a screaming match because you dared to question the greatness of Kurt Angle, but judging by what I see at most boards, many fans don't have those reservations.
But I'd be guilty of the exact same reaction if you shift the form of entertainment being discussed. People can try and tell me that Bob Dylan is the greatest of all time, but from my perspective, he's just some tone-deaf old dude singing boring ass songs about hippie shit when compared to Wu-Tang or Mobb Deep. Hell, I'm not even willing to watch a movie made before the first Star Wars! And nothing anyone can say will ever change that, as Bone Thugs will always be the album playing the first time I saw snow falling, 2PAC will always be the first album I played when I got my first car, and Keith Sweat will always be the artist on the radio when I got my first handjob. Despite being a huge fan of wrestling, I can distance myself from those kinds of emotional connections when thinking about whether 80s WWF is the best ever, but I don't see why it would be weird to think that most people aren't able to.