10 Greatest Musician Cameos On The Simpsons

8. Sting

The Simpsons Bette Midler

Guest starring in a cartoon world of unlimited possibilities can have a funny way of bringing out the egomaniac in people. Johnny Carson requested to be depicted in a positive light in his guest spot, and José Canseco famously rejected the writers’ approach in “Homer At The Bat”, necessitating a heroic re-write.

It’s unclear whether Sting made any similar demands in “Radio Bart”, but his cameo certainly depicts him in a great light. He’s charitable, proactive, and a commendable digger. The season three episode sees Bart trapped down a well after a prank gone awry, and Sting heads up a drive to release a charity single which will somehow get him out.

It’s a terrific and still relevant satire of performative caring, and Sting, a notable charity activist, plays his part excellently. Indeed he’s so convincing in his natural, dry performance that it’s not entirely clear whether he’s actively sending up his image or if he’s been left out of the joke.


Yorkshire-based writer of screenplays, essays, and fiction. Big fan of having a laugh. Read more of my stuff @ www.twotownsover.com (if you want!)