2. Ric Flair
WWE.comRic Flair was the biggest name in NWA/WCW history along with Sting. They were the unquestioned leaders of that organization. Sting never left there while Flair did. It was a huge deal at the time because Flair was considered the best wrestler of the 1980s and he was still a very valuable performer throughout the 1990s. His longevity is unparalleled. Flair's initial WWE run lasted a little over one year. He showed up in late 1991, was pushed heavily in 1992 as a two time WWE Champion mostly feuding with Randy Savage and was gone in early 1993. It just didn't work out for him. He felt more comfortable in WCW, so he went back there. We didn't know if he would ever return to WWE. Once the dust settled in the Monday Night War and WWE bought out WCW, it was time for Flair to go back to WWE. They had a great role for him as a co-owner of the company. At least it was a great role in theory. It put him in a position of power. It's not like Flair could realistically afford the company, but this is wrestling after all. His time in WWE was awesome in the 2000s. There was no better going away party in wrestling history than what he got during WrestleMania 24 weekend in 2008. The man was in his mid-50s and still performing at a really high level. It's good to know he'll be back on WWE TV regularly in the near future watching along as his daughter Charlotte becomes a force in the divas division.