Vince McMahon spent the better part of the 90s behind the announce desk as a babyface commentator. It all changed in 1997 when Bret Hart pushed him and kicked off a verbal tirade against WWE on an episode of RAW.
Many believe that this was the moment the Mr. McMahon character was born. He quickly began inserting himself into WWE's top storylines and surprisingly turned out to be a believable heel.
Vince McMahon's rivalry with Stone Cold Steve Austin was instrumental in WWE defeating WCW in the Monday Night Wars. He ultimately bought off the competition in March 2001. The past two decades or so have seen McMahon engage in a long string of rivalries.
Being a hated villain, he booked himself to lose most of these feuds, but there have been a few instances where Vince McMahon emerged victorious when all was said and done.
#5 The Undertaker
Back in late 2003, Vince McMahon was doing everything he could to make sure that the WWE title stayed on the shoulder of Brock Lesnar. He helped Lesnar defeat The Undertaker in a Biker Chain match for the WWE Championship at No Mercy 2003.
Thus, a feud started between the two, with The Undertaker challenging Vince McMahon in a Buried Alive match at Survivor Series 2003.
At the event, it didn't take long for Vince McMahon to get busted open. For the next few minutes, The Undertaker destroyed the boss as the crowd cheered for The Deadman in unison. During the closing moments of the match, as The Undertaker was preparing to bury him alive, Kane suddenly appeared out of nowhere and attacked his kayfabe brother.
He dropped The Undertaker into the grave, aiding Vince McMahon in defeating him. The rivalry ended with Vince coming out on top and The Undertaker would come back months later at WrestleMania 20 to exact revenge on Kane.