#3 Vince McMahon - Royal Rumble 1999
The WWE Chairman lasting for nearly an hour, amidst 29 other superstars, in a Royal Rumble match and actually winning it? Surely he had No Chance in Hell.
Turns out he did. In what is arguably one of the most underwhelming Rumble wins of all time, McMahon lasted 56 minutes and 38 seconds of the match by not really being in it. Being drawn #2, McMahon was quick to flee the ring through the bottom rope after taking a few punches from Stone Cold Steve Austin. He would later join the commentary team during the match, still not eliminated, as the match went on. Stone Cold would later bring McMahon back in the ring after being the only two superstars to stay alive in the match, and only a distraction from then WWF Champion The Rock led to Austin’s elimination, thus making McMahon a Royal Rumble winner.
McMahon would relinquish his title opportunity the following night on Raw, the only time a Royal Rumble winner did so.