Can't come up with an accurate HHH top 5. There's a lot of stuff I'd have to re-watch. Say what you want about the guy but he's had more classics (or borderline classics) than most guys from his generation.
Basically. Except Shawn Michaels, I can't think of anybody from that generation.
Why did HHH go over Austin before his WM 17 match with The Rock?
Clique added his perspective, which is true.
The booking reason was, simply, WWE wanted to do the Hunter/Austin feud all over again during the summer, with Triple H as a face and Steve Austin as a heel. Triple H would be the "leader" of WWF/E, while Austin would lead the Alliance and the fact that Triple H had already beaten Austin before would work in Hunter's favor when the Power Trip would eventually implode.
The seeds had already been planted, with Austin retaining the WWE Title with the help of Triple H at Judgment Day 2001, while Hunter lost the IC Title due to a mistake by Austin. The next night during the infamous tag team match against Benoit/Jericho, Hunter's mistake cost their team the match and the psychology of Austin taking the fall was to advance the story line of Austin not being the "Stone Cold" of before. The scheduled matches for them at King of the Ring 2001 was Austin/Jericho and Hunter/Benoit in singles matches. Austin would retain the title thanks to Hunter, but Triple H would end up losing to Benoit due to Austin's interference. Both would eventually implode in the next PPV, with Triple H eventually turning face and wrestling Austin for the title at SummerSlam.
Of course, it never happened, so WWE went ahead with the Triple Threat match at King of the Ring. The entire Alliance program was in a mess because there was nobody big enough to wrestle Austin as the leader of WWE since WWE couldn't capture most of the genuine wCw stars. That left WWE with Rock and Austin only, and they didn't want to do Austin/Rock again so soon after 'Mania X-Seven.