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#8 Triple H on The Drew Carey Show
In the heat of the Attitude Era, Drew Carey made an infamous appearance in the Royal Rumble match. He quickly seemed to realize he was in over his head as he tried to pay off Kane not to hurt him, before eliminating himself to avoid getting mauled in the ring.
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It tends to be forgotten that media crossover worked both ways. Not only was Carey a part of WWE programming, but WWE Superstar Triple H appeared on The Drew Carey Show.
The episode saw him get into a relationship with Kate, played by Christa Miller, with a particularly salacious hint at the two’s bedroom activities as she claimed to have pinned him for his title.
While far from momentous in broader pop culture history. Triple H nonetheless performed nicely for himself in the context, broadening his name value to non-wrestling fans and representing WWE nicely on the much-watched sitcom.
