11. Triple H (1576 Days)
Before racking up 14 world titles, Triple H's career was relatively humble.
He made his TV debut as Hunter Hearst Helmsley on the 30 April 1995 showing of WWF Wrestling Challenge, but his early days hardly set the world alight. Arguably the most memorable moment of his first year was being squashed by the Ultimate Warrior at WrestleMania XII.
Then in 1996, the MSG Curtain Call incident didn’t do him any favours, allegedly resulting in a King of the Ring push being scrapped, and so it wasn’t until the formation of D-Generation X in ‘97 that his career really started to take off. Even then, though, he found himself firmly in the shadow of his partner in crime, Shawn Michaels.
That meant that Triple H had to wait until his buddy’s departure in ‘98 before he'd finally get his own moment in the sun. Emerging as the faction’s new leader, Triple H went on to establish himself as one of the top heels in the company, and on the 23 August 1999 showing of Raw—the next night after SummerSlam—he beat Mankind for the WWF Championship: the pay-off to a 1576-day wait for his maiden world title victory.