You mentioned in a previous answer that HHH didn't become a "tippy-top guy" until his third title reign in January 2000.
I know it's a bit arbitrary, but when would you say the following (if at all) reached tippy-top mount-of-perpetually-over status?
Cena: The HHH match at Wrestlemania.
Bryan: Probably the cage match with Bray Wyatt where he escaped the Wyatt Family.
Punk: The pipebomb would be the obvious choice, but the HHH feud really derailed him for a while. I'd say it wasn't until about 6 months into his title reign that he really solidified himself at that level.
Brock: Winning the UFC title from Randy Couture.
Orton: That whole feud with HHH with the kidnapping and stuff. Yeah, the blowoff sucked, but it really turned him into someone who was the hottest thing in wrestling for a while and he never fell below a certain level again after that, whereas in 2005 there were serious questions about where he would end up.
Rock: The ladder match with HHH at Summerslam 98.
Austin: Duh, the Bret match at Wrestlemania.
Foley: I would argue that he never reached that level. He absolutely managed to diminish his own stardom over the years. On a different level, you could say that Have a Nice Day going #1 opened the door for wrestling books and made him a literary star, but as a wrestler, not so much.
Batista: The HHH matches in 2005. Right out of the gate.
Angle: TAP OR I'LL BREAK YOUR FUCKING ANKLE, ROCK!