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Browne sets up a romantic story about a heart-shaped pendant, then neatly inverts his song title for a grown-up, world-weary assessment of love and the unknowability of the other: "You try so hard to keep a life from coming apart / And never know what breaches and faults are concealed in the shape of a heart." Brutal. Tom Waits, "Hang Down Your Head" (1986) Cowritten by Waits' wife, playwright Kathleen Brennan, "Hang Down Your Head" is one of Waits' most tender songs, capped off by a lyrical Marc Ribot guitar solo.
(It's a rare instance of Ribot not attempting to strangle his guitar.) Playing into Waits' obsession with the archaic, it tells the the oldest breakup story in the book: "You have found another, oh, baby, I must go away." — 20.
— is so stern and authoritative that when "Come Back to Me" drops, it's hard to believe this is our Dear Leader dropping her guard to plead with a departed lover.
That juxtaposition makes it all the more effective, and all the more moving. Hüsker Dü, "Don't Want To Know If You Are Lonely" (1986) With text messages and voicemail replacing the answering machine, the feeling of ignoring a call while listening to someone leave a message is gone forever.
The song is vast, chilling, and completely devoid of The Smiths' usual winking.
But Willie Nelson gives "Always On My Mind" a perfect balance of regret and resolve.
His sandpapery rasp and restrained delivery are the real reason this song — covered by so many others — belongs to him. Paul Simon, "Hearts and Bones" (1983) Conventional wisdom probably gives the nod to "Graceland" (a great one, no doubt), but we've got to go with "Hearts and Bones," an ambivalent masterpiece about Simon's troubled marriage to Carrie Fisher.
Come back next week for the best breakup songs of the '90s, and let us know what we missed in the comments. You're going to get through this, and to help with that, here's a Spotify playlist of this week's list, and here are the greatest breakup songs of the '60s and '70s. The B-52s, "Give Me Back My Man" (1980) This surreal dance track tones down the usual zaniness of the early B-52s (no Fred Schneider on this one at all) for a weirdly devastated story with lyrical echoes of a sea shanty.
For maximum tragic effect, check out this video; Cindy Wilson's frail-little-girl delivery makes the song all the more haunting. Jackson Browne, "In The Shape Of A Heart" (1986) Apparently written about the suicide of Browne's first wife, "In The Shape Of A Heart" came out ten years later, and it has the feel of melancholic reflection at a distance.