#8 Sycho Sid
Although Razor Ramon garnered support as a villain soon after his 1992 debut, Sycho Sid - then known as Sid Justice - experienced a taste of things to come earlier that year. Teasing a heel turn by eliminating Hulk Hogan at the 1992 Royal Rumble, Sid was noticeably more popular than WWE's mega-babyface in their post-Rumble pull-apart.
So much so, WWE even dubbed over the crowd's reaction and re-recorded Bobby Heenan and Gorilla Monsoon's commentary track to position Sid as the unquestioned heel.
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Several years later in Madison Square Garden, Sid once again generated massive fan support as the villain in Survivor Series '96's main event. Like the Knickerbocker Arena audience at Royal Rumble '92, the raucous MSG crowd loudly supported Sid's efforts over a white-meat babyface: a visibly shaken Shawn Michaels.
The swapping of roles for this one night led many fans to consider this as the unofficial starting point for the Attitude Era.