JAKE “THE SNAKE” ROBERTS—$500K

Jake “The Snake” Roberts, whose real name was—wait for it—Aurelian Smith Jr., was an extremely popular character in entertainment wrestling during the late ‘80s and early ‘90s. The man often brought an actual python in the ring, after all. Clearly, it’s why he was named Jake “The Snake” Roberts.

He was, to some degree, one of the first wrestlers who pushed the boundaries of the kinds of gimmicks wrestlers can do to keep audiences interested. He was also a key subject of the documentary Beyond the Mat, which chronicled his attempts to sober up after a life of addiction.