1997: Triple H
Defeating Mankind in the finals, Hunter Hearst Helmsley would capture his first WWF title two years later and would become a 14-time WWE World Champion.
Though The Game still wrestles sporadically, he now spends most of his time backstage, helping to run NXT.
1998: Ken Shamrock
The World's Most Dangerous Man defeated The Rock in the finals to become King of the Ring but would leave the company the following year.
Not seen since in WWE, Shamrock announced his fighting promotion, Valor, last month, and was recently announced for some future Impact Wrestling tapings.
1999: Billy Gunn
The One Billy Gunn was able to topple his DX partner, X-Pac, in the 1999 finals and would engage in a feud with The Rock shortly after.
Inducted into the WWE Hall of Fame as part of DX earlier this year, Gunn was recently announced as a trainer for All Elite Wrestling
2000: Kurt Angle
The Olympic Gold Medalist continued his incredible rookie year in the WWF by defeating Rikishi in the finals of 2000.
Winning the WWF title that October, Angle would return to WWE in 2017 to be inducted into the Hall of Fame, and recently appeared at Raw Reunion.