More tippy toppy questions

Good topic! To carry it on, when do you think these guys became tippy toppy guys

 
Bret Hart
Shawn Michaels
Undertaker
Sting
Any member of the Shield
Ric Flair
 
Bret:  The Yokozuna win at WMX.  Really cemented him as the guy who they go to when they don't have a guy.  I mean that in the nicest way.
Shawn:  In his initial run, Royal Rumble 96, where he dominated the match and won a foregone conclusion.  By that point everyone knew where he was ending up and there was nothing to do that would stop him.  In his second run, it took until shortly after the WM20 three-way, I'd say, at which point we knew he would sticking around for good.  
Undertaker:  I'd say this one was FAST.  He was doing main events against Warrior before he even turned babyface for the first time, and people were more than happy to buy him in that role.  I'd say Survivor Series 91 at the outside, but really he was almost there from the moment he debuted.
Sting:  The Flair match.  Made him a star for life, no fuss no muss.
Shield:  Dunno if any of them are what I'd call bulletproof main eventers yet.  
Flair:  Certainly by the time of the 82 feud with Race he was there.  

Tippy top status


Hey Scott

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
Bryan
Punk
Brock
Orton
Rock
Austin
Foley
Batista
Kurt

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!