#1 The Undertaker
Back in 2003, the world of pro wrestling was high on Brock Lesnar, and Vince McMahon was no different. The Beast had helped Mr. McMahon win back the 100% ownership of WWE against Ric Flair and at No Mercy 2003, the WWE head honcho decided to return the favor.
The Undertaker faced Brock Lesnar in a Biker Chain match for the WWE Championship where a chain was hung above the ring. If retrieved, it could be used as a weapon. Vince would interfere and prevent The Undertaker from getting his hands on the object. Brock capitalized, hit 'Taker with the chain, and retained his title.
In the following episode of SmackDown, The Undertaker won a handicap match against Lesnar and Big Show which allowed him to pick an opponent for Survivor Series. He picked Vince McMahon and the stipulation was a Buried Alive match.
As expected, The Undertaker dominated the majority of the match and dragged Vince McMahon to the burial site. However, after a bit of retaliation and interference from Kane, the WWE Chairman was able to pick up the victory.