#5 Sycho Sid
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Sycho Sid had the look, the size and the charisma of a main event superstar. However, he lacked the in-ring skills to properly wrestle headline length matches.
Therefore his two reigns as WWF Champion were extremely brief. His first title win came in a very good match against Shawn Michaels at Survivor Series 1996, where Sid, the villain was vociferously cheered against babyface Michaels, with the hardcore fans tiring of Michaels's goody-two-shoes character.
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Sid's victory existed solely for the purpose of Michaels regaining the belt at the 1997 Royal Rumble event which hailed from his hometown of San Antonio, Texas in the massive Alamodome which the WWF managed to pull over 60,000 fans into.
Sid surprisingly enjoyed a second transitional reign when he beat Bret "Hitman" Hart on Raw, just weeks prior to Wrestlemania 13. That event saw Sid drop the title for the final time to The Undertaker. Sid would soon leave the company and enjoy greater success as World Champion in WCW.