Vince McMahon (September 16, 1999 - September 20, 1999)
Vincent Kennedy McMahon's father, Vincent James McMahon, had forbiden his son from becoming a professional wrestler. However, the ounger McMahon had always held ambitions of becoming an in-ring superstar and champion.
He finally got his chance with his first ever match at the 1999 Royal Rumble (in which he was victorious, incidentally) and at the St. Valentines Day Massacre PPV, a month later, opposite Stone Cold Steve Austin inside a steel cage.
McMahon's in-ring career continued with a WWE Championship victory on the September 16, 1999 episode of SmackDown in which he defeated Triple H, with assistance from Stone Cold, who was feuding with "The Game" at the time.
Shane McMahon acted as the special referee, yet again. The story here was that Triple H would name his opponent in a title match; instead of choosing a worthy opponent such as Austin, Rock or Undertaker, he selected The Chairman.
McMahon eventually complied. However, Triple H's decision came back to haunt him when Stone Cold interfered, battered "The Game" and draped McMahon on top for the win and the title.
Vince McMahon was champion. However, he would vacate the title days later and put it up for grabs in a six pack challenge at Unforgiven 1999.