2. Eddie Guerrero (2005)
In 2004, Eddie Guerrero went on one of the most amazing babyface journeys in the history of WWE. After overcoming a drug addiction and a firing from World Wrestling Entertainment, Eddie had triumphantly returned to the company, and by 2004 had become one of their most popular wrestlers. In February of that year, after winning a battle royal to become the number one contender, Eddie Guerrero defeated one of the best big men in the history of the company, Brock Lesnar, to win his first and only WWE Championship. He followed that up with a classic match at Wrestlemania XX, where he outsmarted Kurt Angle to retain the gold. Eddie Guerrero had become the ultimate underdog story, and so fans were simply not receptive to someone who had overcome so much adversity being a heel. To add to the unsuccessful heel turn was the bizarre storyline Eddie became engaged in, feuding with long-time friend Rey Mysterio over custody of Rey's son Dominick (yes, you read that right). Tragically, Eddie passed away in November of 2005. As fate would have it, however, Eddie had turned face in his last few weeks on earth, and got to spend his final days doing what he loved best: entertaining the fans and basking in their cheers.