Jake is rightly recognised as one of the biggest underachievers in professional wrestling, and one of the greatest never to win a world championship. He had it all: a unique gimmick, bags of in-ring talent, and a dark charisma. Struggles with alcohol consumed him and brought his career to a sadly early end, but some of his work in the late 80s and early 90s would easily be worthy of a WrestleMania main event. Roberts would have provided a true taste of something different, a quietly terrifying heel in an era of musclebound giants and loudmouth managers. Most Likely Opponent: Randy Savage. One of the most iconic moments of wrestling's golden era was the sight of Damien, Jake's pet snake, slowly strangling the life out of the Macho Man in a horrifying post-match assault. Similar antics on the grandest stage of them all would have got the crowd behind Savage like never before.