#5 Stone Cold Steve Austin
Vince McMahon and Steve Austin feuded for the majority of the Attitude Era but the duo took their rivalry to a WWE ring only during the controversial angle involving the Ministry of Darkness.
Led by The Undertaker, the Ministry of Darkness kidnapped Stephanie McMahon twice. During the second instance, The Deadman tried to marry Stephanie but the latter was saved by Austin.
Vince McMahon was eventually revealed as the "Higher Power" controlling the merged The Corporation-Ministry of Darkness faction known as Corporate Ministry.
Vince's McMahon's wife Linda and Stephanie were so shocked that they transferred their 50% stake in WWE to Steve Austin. To gain back the control of the company, a handicap ladder match was set up with Vince and Shane McMahon going against Stone Cold Steve Austin at the 1999 King of the Ring PPV.
It was a brutal affair with Vince McMahon and Steve Austin going at each other. Eventually, while both men were down, Shane climbed the ladder to claim the briefcase and win the match for him and his father.