Nearly every major rock star has appeared on The Simpsons, including three Beatles, Tom Petty, Mick Jagger, and the Ramones. Bruce Springsteen is probably the most famous rocker to not make a tour stop in Springfield. It's not for a lack of trying on the part of The Simpsons' staff, however. The Boss was asked to appear several times, and he always said no.

For example, the 1991 episode "One Fish, Two Fish, Blowfish, Blue Fish" finds Homer convinced he's about to die after eating poisonous fugu at a sushi place, and he takes solace in a book-on-tape version of the Bible narrated by Larry King. The show's staff had wanted Springsteen to be Homer's pre-recorded voice of comfort. And in the 1992 episode "Radio Bart," Sting (playing himself) heroically digs Bart out of the abandoned well into which he's fallen, but that role was also made for Springsteen. And in the 1998 episode "When You Dish Upon a Star," Homer drives Alec Baldwin and Kim Basinger to near madness, but the Boss was an early possibility to be the central celebrity ... except that he said no.

In his book Springfield Confidential, Simpsons writer and producer Mike Reiss said the show resorted to nontraditional methods to book Springsteen. As Reiss put it, "We sent him a Simpsons jacket as a bribe, which didn't work. We even had his sax player, Clarence Clemons, on the show, hoping he'd tell Bruce how much fun it was. That didn't work, either."