Songfacts®:

• This story song is the centerpiece of John Mellencamp's debut album, Chestnut Street Incident, written when he was 25 and just getting his feet wet as a songwriter. The song finds him struggling to get by in a small town, biding his time until he can achieve his dreams.
  
  Mellencamp got a lot better as a lyricist. Check out this passage from this track:
  
  The young girls fall back and say
  There goes that sleek young silhouette
  He don't drive no Corvette
  But he stings just like a Sting Ray
• Chestnut Street is a real street that runs through downtown in Mellencamp's hometown of Seymour, Indiana. The title never shows up in the lyric.
  
  Like Bob Seger, who was a big influence on him, Mellencamp's songs were often based on people and places he knew well. Before getting his record deal, he was working a minimum-wage job at the phone company, so he could certainly relate to the character he created.
  
  Note that while he seems embittered in this song ("I'm just a small-town boy bein' used like a toy"), he's not trying to escape Chestnut Street, just make a better life for himself there. Pride in his small town - warts and all - is a common theme in his songs.
• At the time, Mellencamp was known as "Johnny Cougar," a name his record company insisted he use, much to his dismay. They also positioned him as heartland sex symbol, showing him on the album cover in full James Dean mode. For the notoriously hard-headed Mellencamp, this was tough to swallow, but he methodically worked the system until he could call his own shots. The Chestnut Street Incident was a failure, but Mellencamp learned to write songs with more pop appeal and managed a minor hit on his next album: "I Need A Lover." After landing huge hits with "Jack & Diane" and "Hurts So Good" from his 1982 album American Fool, he was emancipated, using his real name from that point forward.