20. Eddie Guerrero, $509,553 In 1999
One of the best wrestlers of his generation, Eddie Guerrero was making an impressive half a million dollars in 1999. He was important to the latino audience, and a go-to guy for putting on exciting matches. However, he missed a lot of 1999 due to the serious car accident he suffered on New Year's Day that year. It is a little surprising that he still managed to earn so much money when he was absent January to June. Half a million certainly wasn't bad and he was earning more than his friend Chris Benoit. Still, he ended up jumping ship to the WWF with Benoit at the start of 2000.