11. Dolly Parton, “Down From Dover” (1970)
You pretty much don’t know sad until you’ve heard this Dolly Parton song about a pregnant young girl, abandoned by her family and baby daddy. The lyrics kill and Dolly’s mournful twang could melt even the coldest of hearts. The protagonist holds on hope that her only love will return, but he never ever does. As if that weren’t sad enough, what happens next? Her baby up and dies! At the end of the ballad, the poor thing has no one left to love at all. Penned by Miss Parton at the tender age of eighteen and banned from radio due to its controversial nature, “Down From Dover” is unfairly emotionally manipulative, yet undeniably brilliant. It’s the anti-Juno. Sofi Papamarko
12. Bob Dylan, “Don’t Think Twice, It’s All Right” (1963)
The real sadness of Bob Dylan’s “Don’t Think Twice, It’s All Right” comes not from the fact this guy and girl are totally done, but that this guy is so sure they’re done that he’s decided to phrase everything in negative constructions: “It ain’t no use,” indeed. But beneath the bravado, there’s hurt in him, too. The line that’s always haunted me is “You could have done better, but I don’t mind,” which sounds like precisely the sort of self-preserving rhetoric one expects from a ten-year-old who is trying to dismiss the fact that you just stole his toy. Or, you know, a twenty-two-year-old kid who’s had his heart broken. JB
13. Bruce Springsteen, “The River” (1980)
“Then I got Mary pregnant, and man that was all she wrote
And for my 19th birthday, I got a union card and a wedding coat”
While Ronald Reagan campaigned on a promise of Morning in America, 1980 saw Bruce Springsteen drawing his characters from ever deeper within the country’s gloom. The Magic Rats and Puerto Rican Janes that featured in his early successes were gone, replaced by factory workers and women with wrinkles around their eyes, as Springsteen’s interest shifted from romantic street fantasies to the lives of the blue collar people he’d grown up around. The title track of his double album, “The River” tells the story—based on the experiences of Springsteen’s sister—of a couple who find themselves too old too soon, dead-ended by a shotgun wedding and a recession, turning in on themselves and away from each other. The song’s haunting harmonica part and wordless coda are among the most powerful moments in Springsteen’s catalogue. JT
14. Sinead O’Connor, “Streets of London” (orig. 1969)
Sinead’s version of Ralph McTell’s widely covered 1969 track is an ethereal, reverb-heavy recording fit for plugged-in subway rides, studying strange faces. Each verse is a somber, lilting meditation on the city’s forgotten characters. “Have you seen the old man/ In the closed down market / In his eyes you see no pride / Hands held loosely by his side / Yesterday’s paper, telling yesterday’s news.” Sinead whisper-sings through each melancholy portrait, uttering each word slowly and plainly. Her mildly-intoned rebuke in the chorus (“So how can you tell me you’re lonely?”) packs the hardest punch. The bottom line: Life sucks worse for other people. Quit feeling sorry for yourself. Claire Ward
15/16. Buffalo Tom, “Taillights Fade” (1992) / Red House Painters “Katy Song” (1993)
One of the most important reasons sad songs exist—obviously—is to help you get laid by looking sensitive. And back in the heart-on-your-frayed lumberjack shirt-sleeves Grunge era of the early 90s, nobody embodied the “horniness disguised as empathy” ethic better than Buffalo Tom and the Red House Painters. It doesn’t hurt, of course, that both of these songs are absolute killers. PI
Next: Mahalia Jackson, Swamp Dogg, Gram Parsons, Neil Young
