The Simpsons’ Showrunner Al Jean gives the background of the 10 favorite Songs as picked by the writers of the perennial animated sitcom
10. “Capital City” from season two’s “Dancin’ Homer.” In this song by Jeff Martin, Tony Bennett extols the virtues of Springfield’s state capital, which includes the crosstown bridge, the Penny Loafer, and 4th Street and D. The song helped Tony Bennett reach a younger audience, but did nothing to help The Simpsons reach an older audience. [Co-creator] Sam Simon reached out to Bennett. There was an internal debate over whether or not to have a guest star playing himself. We hadn’t done that before. The real world won.
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