8. John Prine - 'Sam Stone'
Injured war vets and heroin addicts are both great subjects for sad songs. John Prine managed a rare feat in 1971 when he combined them both in his hit song "Sam Stone." It's about a Vietnam War veteran returning home with a taste for smack. He's eventually reduced to robbery to feed his habit. The chorus is one of the saddest in pop history: "There's a hole in daddy's arm/ Where all the money goes/ Jesus Christ died for nothing/ I suppose." He dies at the end after "popping his last balloon" in a "room that smells just like death."