My personalized radio station on Launch just played a Graham Parker song I haven't heard before: "I'll Never Play Jacksonville Again."
Since the city is 45 minutes to the north, I was amused to hear one of my favorite singers vowing never to come back. The St. Petersburg Times has written about the song, which has a much sadder origin than I anticipated.
You may also want to look for the song Jacksonville by Matt Keating. It's (slightly) less gloomy.
I can't find the song, but some local artists got airplay here a few years ago for "Chill in the 'Ville," which mentioned Regency Mall and other local things. There's also the infamous "Uh Oh," the Jacksonville Jaguars 1999 Super Bowl song recorded by Keenan McCardell and a few other players, much to the enjoyment of the Tennesee Titans after they clobbered the Jags in the AFC Championship game.