He guest starred on The Simpsons in “Stark Raving Dad," as the speaking voice of Leon Kompowsky under the pseudo-John Jay Smith. Jackson was a fan of the show. He called Matt Groening one night and offered to do a guest spot. The idea for the episode was presented by James L. Brooks, and Al Jean and Mike Reiss wrote the script. Jackson's favorite character was Bart.
Michael Jackson wrote much of the song, "Do the Bartman," even though he did not receive credit for it. He also wrote the song, "Happy Birthday Lisa," which was later included in the album, "Songs in the key of Springfield." One of the conditions for guest starring was that he voiced himself, but a sound-alike would receive credit. While he recorded the voice work for his character, his singing was performed by Kipp Lennon, because Jackson wanted to play a funny joke on his brothers and fool them into thinking the impersonator was him.