10 Best Simpsons Guest Stars (Who Played Themselves)
6. Simon Cowell
Simon Cowell actually appears twice in The Simpsons, though only once as himself. However, his first appearance in Season 15’s Smart & Smarter, he played preschool examiner Henry, a parody of himself so bad it hurt.
In fact, when Cowell returned in Season 21’s Judge Me Tender, they didn’t even change up the character model used. His return is in a Moe episode, something they usually have once a season now, and can be hit or miss. Eeny Teeny Maya Moe and King Leer were fantastic, while Moe Goes From Rags To Riches was one of the worst episodes ever.
Judge Me Tender is on the better side of average, largely down to Simon Cowell and Hank Azaria’s chemistry together. The plot involves Moe’s cynical personality seeing him become a popular judge, first of small time Springfield shows, then the big leagues as he joins American Idol.
At first Cowell takes him under his wing, but sabotages Moe the second he starts to upstage him. What makes a fairly standard premise so great is how willing Cowell is to mock himself, and how over the top he parodies his judging persona.