King of the Ring Back in 2000
Why not to start with Shane’s next opponent? Back in 2000, The Undertaker was running his American Badass character, which was...hit-or-miss. However, this six-man tag match (The Rock, Kane, and Undertaker vs. The McMahons and Triple H, for Haitch’s WWF Championship) definitely delivered, with a bunch of convoluted violence that led to the climactic flying chokeslam, from the top rope all the way down to the announcer’s tables.
This was one of the first times where Shane was seen not just as an entitled rich kid, but someone willing to take the bumps to keep up (and surpass at times) the boys in the back. Looking back at it, the flying chokeslam seems almost same with what Shane would eventually do; at the time, however, it was certifiably nuts that the heir to a billion dollar company would let one of its employees demolish him like this. We were so young and foolish then.