#2 Bret Hart on The Simpsons
By 1996, Bret Hart was not only a WWE veteran but a multiple time WWE Champion, entrenched as one of the company’s definitive top stars. So, it made sense enough that when The Simpsons looked to collaborate and bring in a WWE star to voice a part and be animated, they’d select The Hitman.
Ironically, Hart reported later in interviews that the show’s makers wanted him to play a more generic wrestling character and put on a different voice, and only changed their minds to capture Hart more true to life after they realized how big of a star he was.
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Hart appeared on the show as a potential buyer for the Mr Burns character’s mansion, underscoring that with his wrestling success he had become a wealthy man who could afford such a property. It was an oddball spot for the straight-laced Hart, in a sense.
However, the guest spot also fit Hart’s well-documented passion for cartooning himself, as he was finally rendered into one of the most famous cartoons of his generation himself.