The River, 1980
Talking about the ways in which rock & roll can capture joy as well as bleakness, Springsteen once said, "How could a happy song like 'Sherry Darling' coexist with 'Point Blank' . . . ?" Swept along by Roy Bittan's dramatic piano, this grand passion-play ballad was indeed one of Springsteen's gloomiest relationship songs. Although he's never discussed who inspired it, it's long assumed the woman in the song is an ex who dealt with drug problems.