5. The Undertaker
WWE Tenure: 23+ years Remember when WWE hyped Undertaker's decade of destruction? That was well over 10 years ago. And in 2014, The Deadman is really starting to seem immortal. Undertaker debuted years before guys like The Rock and Steve Austin did. He's outlasted many of the company's big names, and helped bridge the past couple eras. It was on Nov. 19, 1990, that Mark Calaway slapped on a trenchcoat, put on a stetson hat and became an integral part of WWE history. No wrestler who has ever been employed by Vince McMahon has stuck with him so long, and remained so popular. When you think of Undertaker, you think of the WWE. Yes, he competed in WCW briefly, but it was Vince who gave him a new home, and his first real opportunity. Taker has always remained loyal to him, and never jumped to WCW for a huge payday like so many of his co-workers did. Taker is the most respected wrestler in business, and at the age of 48, still shows up from time-to-time delivering great matches that put men half his age to shame. It's tough to say how much Taker will keep going, but it's safe to say that he can as long as he wants to.