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Sting had a heel turn in 1999 that always stood out in my mind as being really terrible. He was headed towards a title match at Fall Brawl 1999 against Hogan who had himself recently turned face and gone back to his red and yellow, trunk-wearing ways after the nWo died out.
So Sting and Hogan finally had mutual respect from one another after years of being rivals. That didn't sit well with Luger, who tried to drive a wedge between them. Luger kept telling Sting that Hogan was untrustworthy, and reminding Sting of all of the times he'd been double crossed in the past.
Ultimately, Sting was the one to turn and he sided with Luger. It just didn't work at all. The crowd had zero interest in booing Sting, the one guy they'd reliably been able to cheer from the beginning of the company. He kept getting cheered and the whole thing bombed.
Sting was back to being face by November, at which point Luger turned on him. Because of course he did.
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