We start with a guy who was inducted into the WWE Hall of Fame in 2014, but he makes it into that illustrious club without ever claiming a major championship with the company. With such a unique gimmick, Jake Roberts became a hugely popular guy in the eyes of WWE fans. Unfortunately - like several other stars on this list - he wrestled at a time when the industry was being dominated by guys like Ric Flair, Hulk Hogan and Randy Savage. That meant he never really got a shot at the big time. Amazingly, Roberts never won a championship of any kind whilst wrestling for the WWE. For a man who garnered as much popularity as he did, that is a pretty astonishing feat.