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#2 Grandmaster Sexay: 2004
WWE Hall of Famer Jim Ross was the Vice President of Talent Relations for almost a decade in WWE. When he stepped down in 2004, he signed one more superstar to a contract as his final duty, and that would be the returning Brian 'Grandmaster Sexay' Lawler, as a favor to his friend and Brian's father, Jerry Lawler.
Grandmaster had a wildly popular tag team with Scotty 2 Hotty as Too Cool during the Attitude Era, but WWE clearly had no plans for him when he returned in 2004. Grandmaster returned to RAW in April 2004, immediately being squashed by Kane. The following week he lost a quick match to Christian on RAW, then picked up a win over an enhancement talent on an episode of Heat, before losing to Lance Cade on Heat the following week. Grandmaster would be fired a few days later, having his return last just one month. Grandmaster was fired after he showed up very late to a live event, as well as being suspected of being under the influence of something.
Ironically at the time of Lawler's return to WWE, his former Too Cool teammates Scotty 2 Hotty and Rikishi were the WWE Tag Team Champions on Smackdown, and 2 weeks into his return, they lost the titles and Rikishi got injured. It would have made complete sense to send him over to Smackdown to reunite with Scotty, but for whatever reason, that didn't happen. Grandmaster has since made appearances and wrestled on WWE TV in 2011 and 2014.
