10 Greatest Musician Cameos On The Simpsons

Perhaps the most surprising casting success of the bunch, Jackson’s appearance on The Simpsons was shrouded in secrecy. Due to contractual issues, the King Of Pop was credited under a pseudonym, and was forbidden from singing on the show (despite his pre-existing relationship with The Simpsons, having co-written “Do The Bartman”).

The producers leaned into this issue, though, having Jackson portray a mental hospital patient who befriends Homer. The hulking Leon Kompowsky looks imposing but believes himself to be Jackson, something he manages to convince Homer of by way of a vocal performance (performed by a soundalike - it’s all very confusing).

Jackson was never the most natural of actors, but he brings his otherworldly superstardom to the role, and clearly enjoyed being part of the production. He even chipped in with another Jackson original, co-writing “Happy Birthday Lisa”, an impossibly catchy throwaway.

While his presence in just about anything is controversial these days, Jackson’s willingness to give his time, make fun of himself, and investigate the plight of the mega-megastar is rare in comedy, and he provides a quality no one else could.