#1 Vince McMahon
Before the much-maligned Vince Russo made Hollywood actor, David Arquette and later himself WCW World Champion, Vince McMahon's ego ran wild to the point where he booked himself to become WWF World Champion in September 1999.
From a storyline perspective, the title change worked in context as it was effectively Stone Cold Steve Austin who beat then WWF World Champion, Triple H to further their feud when he placed a fallen McMahon on top of the "Game" to win the title.
Will John Cena beat Ric Flair's record? A former WCW Champion thinks so HERE
McMahon, unsurprisingly was and still is the oldest title holder in the belt's 55 year history and his reign was mercifully short when he vacated the belt and held it up in a six-way match at the next pay per view event, Unforgiven, where Triple H would regain the belt which very much made the whole exercise seem pointless.