Gene Pitney - Town Without Pity. Don't judge Gene for his slightly creeper demeanor here. The town did this to him. The town without pity. Some of you will understand and I hope you got out of there, man.
Skeeter Davis - The End of the World. The ultimate anthem of the deeply depressed. The studio recording is haunting and will somehow make you feel better, bubby.
Dolly Parton - Jolene. It's a foregone conclusion that Jolene will be taking Dolly's man. But what a lovely plea. He wasn't worth it.
Peggy Lee - Black Coffee. The guy didn't call. You know the type. Is that all there is?
Nancy Sinatra - Bang Bang. No, Nancy--don't get involved with that gun nut! Too late. Damn.
The Temptations - Papa was a Rolling Stone. Disappointment in a parent--does it ever entirely go away? I need to start a blog completely dedicated to The Temptations. What a run they had.
Amy Winehouse - Will You Still Love Me Tomorrow? If you have to ask... *sigh*