Especially since he isn't a main performer when he does compete Shane seems to sneak in a CMOA each match. It arguably began when he dropped an elbow from the top rope to the announce table on Test in his match at Summerslam 99. He'd then up the ante and in 2000 drop the elbow from the stage, then do a diving elbow from the top of the titantron.
The death of WCW. His father Vince has the Raw and Nitro telecast at the same time where he is about to announce his buyout of the company. Cue Shane appearing on Nitro.
"The deal is finalized, and the name on the contract does say McMahon..." (Crowd roars as Vince's eyes bug out at the upcoming swerve) "However, it reads ShaneMcMahon.I now own WCW!"
His match against his father at WrestleMania XVII. After special referee Mick Foley beats down Vince in the corner Shane places a garbage can in front of him, then leaps up the other side of the ring. No, no way, he can't do it, he doesn't have the leg strength. Shane says his prayers and uses his hand to make the cross. He's not gonna...coast to coast missile dropkick into Vince.
Every time you think you've seen every HSQ moment there is to see in WWE, along comes Shane O'Mac to remind you that even the boss's son can be a total badass. Case in point: the Street Fight against Kurt Angle at King of the Ring '01. Thirty minutes of Shane going toe-to-toe with an Olympic gold medalist and more than holding his own. This is the match that gave birth to "That Spot with the Glass", a truly frightening moment when Shane was thrown into plate glass five times, going through it twice and landing on his head the other three times.
It gets more badass when you listen to Angle and Shane's interviews about the match. Turns out every time Angle suplexed Shane into the glass and it didn't break, Angle told Shane they should skip the glass spot move to the next spot in the match but Shane kept telling him to throw him again.
Put it this way: that spot was so infamously hardcore that Vince McMahon was reportedly furious that his son would be so foolish as to go through with something like that. When you can get the boss to draw a line in the proverbial sand, you are pretty hardcore.
He and Angle also got a standing ovation from the guys in the locker room afterwards.
His two matches against Kane in 2003, first in a Last Man Standing match at "Unforgiven", then in an "Ambulance Match" at Survivor Series.
The Ambulance Match, keeping the HSQ in check, included not only Shane backing up an SUV hard enough to send Kane flying backwards into a toll booth, but also delivering a coast to coast missile dropkick to Kane with the help of steel steps. Did this troper forget to mention he did it from the top of the ambulance?