[Lists like this--and there are a lot of them online--almost invariably include Johnny Cash's "Folsom Prison Blues." Far be it from me to diss the Man in Black, but I picked 5 different songs.]
54-46 Was My Number by Toots & the Maytals
An autobiographical song about the consequences of Toots' tokes.
Neko Case: Prison Girls
I love your long shadows and your gunpower eyes.
Sam Cooke: Chain Gang
Never before has hard labor sounded so good.
Dum Dum Girls: Jail La La
When it's time for Dee Dee's phone call, she finds she can't remember anyone's number.
Zombies: Care of Cell 44
"Good morning to you. I hope you're feeling better baby," sings Colin Blunstone, and at first you think you're listening to your typical love song--albeit one with fantastic Beach Boys harmonies. Then comes the kicker: "We'll get to know each other for a second time. And then you can tell me 'bout your prison stay."