7. Triple H
WWE Tenure: 18+ Years Debuting a mere two months before Kane, Hunter Hearst Helmsley made his televised WWF debut on April 30, 1995. From his humble beginnings of playing the character of a rich snob, he eventually worked hard, rose his way up the ranks, married the bosses' daughter and became a rich snob in real life. He lived the American dream, and took up more WWE TV time this past 18 years than anyone else. It was clear from the start that HHH would have a lengthy career. Shortly after his jump from WCW, The Kliq quickly accepted him as one of their own. Even better for him, he didn't have the personal vices that they did, and for the most part (the Curtain Call incident aside) kept out of trouble. Even though his buddies soon left for the big money contracts that Eric Bischoff was offering up, he remained with the WWF. You can imagine that Vince appreciated his loyalty. Hunter is a student of the business, which has helped him earn the trust of his father-in-law, and kept him at the top of the card since the late 90s. Right now, he's one of the last remaining talents of the Attitude Era to still compete on WWE TV. He's even been employed full-time longer than his wife has in the company. And since it's looking increasingly likely that he'll inherit the WWE along with Stephanie, he should be around for decades. The Game has just begun.