Songfacts®:

• Rickie Lee Jones was reared on beat poetry and developed a bohemian look and style in the process. "Coolsville," is probably her best example of this poetry put to music. The song tells a vague tale of a conflicted relationship, using card games as a metaphor:
  
  I jumped all his jokers
  But he trumped all my tricks
• Jones gave off a saucy swagger in this song that played up her image as the coolest chick in town. It was included on her debut album, which showed her wearing her beatnik beret and smoking a skinny cigarette. The album was wildly successful, earning Jones a Grammy Award for Best New Artist. In one of the first national stories on Jones, Time magazine called her "The Duchess of Coolsville" in praising her work. Jones carried that moniker throughout her career, even using it as the title of her 2005 anthology album.
• In a 2011 interview with Mojo, Jones explained that the character in this song represents one side of her personality. "The persona that you're creating is made up of you - but it's the best you think you are, the coolest you think you are," she said.
• Jones performed this song (and her big hit "Chuck E.'s In Love" when she was the musical guest on Saturday Night Live, April 7, 1979. She started the song smoking a cigarette, presumably a Winston to go with the line, "In the Winston lips of September."