10. Gypsy Joe (77 years 36 days)
Gypsy Joe wrestled in and won championships in Canada, Puerto Rico, and the United States. He used a brawling style that helped him become one of the forefathers of hardcore wrestling. Though his encounter with New Jack might be his most infamous moment, Joe’s career in wrestling spanned 7 decades with his last match taking place on January 7, 2011, at the Gypsy Joe retirement show in Tullahoma, Tennessee.
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