6. Jerry Lawler
WWE Tenure: 21+ Years Who would have guessed that one of Vince McMahon's biggest competitors would become one of his most tenured employees? Besides quitting the WWE for 10 months in 2001 when his girlfriend The Kat was fired, Jerry Lawler has been a part of the WWE family since 1992. He ended up joining the company after years of success in various territories, and even booking a few of his own. While he was a wrestling legend upon his debut, the WWF didn't often rely on him for in-ring duty. Sure, he had a feud with Bret Hart, and competed in the King of the Ring tournament, but after that, he transitioned into a full-time role of announcer which he's held onto to this day. Part of his longevity must be attributed to his success in transitioning from a cartoonish character in the New Generation era, to a perverted older man in the Attitude Era to Uncle Jerry for today's fans. He may have also gained Vince's respect when the two shared the announce table for a a few years. Perhaps only Jim Ross' voice has been heard more on WWE TV the past 20 years than The King's, which made his on-air heart attack in 2012 all the more shocking. Thankfully, he appears to have fully recovered, and you can imagine that he'll be involved in the WWE in some form for the rest of his life.