10 Superstars from WWE in 2000 who’ll enter at least their third decade with the company in 2020

#3 Triple H (1990s, 2000s, 2010s, 2020s)

Triple H has proven to be one of the most gifted entertainers in the industry

Triple H signed a contract with World Championship Wrestling (WCW) in 1994. He was let go from that contract and quickly signed with WWE in 1995. He became known as the Connecticut Blue Blood Hunter Hearst Helmsley and made his in-ring debut at SummerSlam that year, where he defeated Bob Holly.

That marked the beginning of a remarkable career that has spanned almost two and a half decades. Almost every gimmick Triple H touched turned to gold in WWE, and his factions D-Generation X and Evolution are known as two of the best factions in the company’s history.

Over the span of 25 years, Triple H has won 14 World Championships, and several other championships to become one of the most decorated stars in the industry.

In recent years, Triple H has been working as an executive in the company and after the passing of Dusty Rhodes, began to dedicate a significant amount of time to NXT, which has developed into another great wrestling brand for the company.

Since putting on the suit, Triple H has featured in far fewer matches than he used to during his early days. His most recent match was at this past year's WrestleMania 35, defeating Batista in the latter's retirement match. The Game has always returned to the ring to reignite some great angles, and we’re sure he won’t hang up his boots without having a retirement match of his own.