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for me its got to be HHH at mania 15. they set that up perfectly to have chyna turn face and than have them both turn heel
 

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I think the heel turn that shocked me that a lot of people won't bring up is when Kurt Angle joined the Alliance.... everyone at the time was like wtf? Didn't he spray WCW/ECW with the Milk Truck a couple weeks ago? It was shocking, but stupid
 

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Hogan at Bash of the Beach '96.

If we're doing WWE only, I'd probably go with Austin at Wrestlemania X-Seven.
 

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Austin's at WM 17 ...I took me about a week to understand why the fuck would they do this?
 
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