#5 Terry Funk
Despite being best known as a "Hardcore wrestler" and a member of the famous Funk wrestling family, Terry Funk was a former NWA Heavyweight Champion in the 1970s and worked a program in WCW at the top of the card against Ric Flair. Funk held the title for over a year before he lost it to another NWA legend in Harley Race.
After wrestling for WCW, Funk wrestled for ECW. Funk won the ECW World Heavyweight title in 1997, 20 years after he won the NWA Heavyweight title. Funk defeated Raven for the title and hold it for almost 4 months before losing it to Sabu.
In WWE, Funk was used as a hardcore wrestler more than a serious main event talent. While his first run with the promotion saw him challenge Hulk Hogan for the WWF World Title, he never won the belt. When Funk returned to WWE in the late 90s as Chainsaw Charlie.
During this time he won his first, and only, WWE title when he teamed with Cactus Jack to win the Tag Team titles.