The Saddest Music, Part 4

17. Mahalia Jackson, “Trouble of the World” (1959)



If you haven’t cried during a Douglas Sirk film, you’re either dead or have boundlessly good taste. But even outside of its narrative context, this clip of Mahalia Jackson singing at a funeral—from Sirk’s Imitation of Life—packs more heartbreak into its two-and-a-half minutes than a lifetime’s worth of Lifetime movies. PI




18. Neil Young, “Borrowed Tune” (1973)



Calling “Borrowed Tune” the saddest song on Neil Young’s Tonight’s the Night is sort of like arguing that the duck is the birdiest part of a turducken. Despite its gloomy surroundings—the album is predicated on the death of two of Young’s friends—this one’s top of the pile, sort of the Platonic ideal of a song you listen to at four a.m. while drinking whisky alone after being broken up with over the course of a long, sad party. Add since Young’s sitting “alone in this empty room, too wasted to write [his] own” melody, you’ve got a partner in misery. JB




19. Gram Parsons & Emmylou Harris, “$1,000 Wedding” (1974)



“But where are the flowers for my baby
I’d even like to see her mean old mama
And why ain’t there a funeral if you’re gonna act that way”


Gram Parsons knew his way around a heartbreak song, and some of his saddest were borne of personal experience. Parsons’ girlfriend Nancy Ross gave birth to their daughter Polly in 1968. Parsons proposed to Ross out of a sense of responsibility, but his musician’s lifestyle and worries about fatherhood and commitment drove them apart. Before their break-up, the singer commissioned a $1,000 wedding dress for Ross from Nudie Cohn, the “rhinestone tailor” who made Parsons’ flamboyant cosmic cowboy suits. The dress was never used, but it helped inspire this song from his 1974 album Grievous Angel—a tale of a groom abandoned at the altar, the last among those gathered for the ceremony to learn that his bride has left him. JT



20. Lee Hazlewood, “My Autumn’s Done Come” (1966)



Because there’s sad, and there’s tragic. And then there’s Lee Hazlewood. PI




21. John Prine/Swamp Dogg, “Sam Stone” (1971/1972)





“There’s a hole in daddy’s arm where all the money goes,
Jesus Christ died for nothin’ I suppose.”


Soldier comes back home from Vietnam with post-traumatic stress disorder, overdoses, dies. The end. True story, so I’ve heard. John Prine’s original is devastating enough, but Swamp Dogg’s funereal rearrangement is even worse. PI


Next: Notorious BIG, Judy Garland, Jewish refugee mice

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