John Keats defines melancholy in his famous Ode as "the wakeful anguish of the soul". Each of these songs embodies that feeling in some way. Notice I've chosen songs that are melancholy without being sentimental, a key difference. For instance, Chet Atkin's "I Still Can't Say Goodbye" is a great song, but it's sentimental, not melancholy. And something like Clapton's "Tears in Heaven" isn't just sentimental, it's bathetic.
"Martha" ~ Tom Waits
Growing old, thinking of past loves, wishing you could turn back the clock and knowing you can't.
"Houses on the Hill" ~ Whiskeytown
A series of images, about war, death, and lost love—and in less than three minutes. Perfect for dark nights driving on back country roads.
"Angel" ~ Aretha Franklin
She's the Queen of Soul, but here, in a song written by her sister, Aretha's voice hits high notes of longing and desire as she sings of getting older, looking for someone to love … and never succeeding. The interplay between instruments in the middle—saxophone, strings, french horn, and then organ—is moving, one of a kind. They don't make them like this any more.
"Sweet Old World" ~ Lucinda Williams
An elegy for a friend who committed suicide, detailing all the good things in life that he left behind: "The breath from your own lips, the touch of fingertips, A sweet and tender kiss, The sound of a midnight train, wearing someone's ring, Someone calling your name, Somebody so warm cradled in your arm, Didn't you think you were worth anything?"
"In Spite of Me" ~ Morphine
Perhaps a bit too menacing to be truly melancholy, and perhaps a touch too bitter as well. But underlying it all is melancholy, directed at the self as much as the one he sings about.
"Landslide" ~ Smashing Pumpkins
A fantastic remake of a Fleetwood Mac song. Just Billy Corgan and a guitar. His voice can be whiny sometimes, but here's it's perfect. Coupled with a spare yet resonant arrangment, this is a beautiful, aching song.
"God Only Knows" ~ The Beach Boys
Before you laugh, go listen to the lyrics again. The first line, after all, is "I may not always love you …", and it goes from there, wondering, hoping, promising only that he can't promise anything. And the music? Brian Wilson has never been more lovely … or catchy. (Yes, "In My Room" is melancholy … but it's also too obviously melancholy. "God Only Knows" sneaks up on you in a way that the other does not.)
"Moonlight Mile" ~ The Rolling Stones
One of the greatest finishes to an album in all of rock, this song communicates weariness better than almost any other song I know. Yet those sweeping violins at the end provide a note of resolve and hope. A brilliant six minutes …
"All I Want Is You" ~ U2
… which U2 echoes perfectly—down to the strings!—for the close of their underrated album Rattle and Hum. If "Moonlight Mile" encapsulates one type of early '70s melancholy, then "All I Want Is You" does the same for the late '80s.
"Around the Bend" ~ Pearl Jam
It's not their greatest, but so many of their songs are about personal loss, about people who are no longer present physically or emotionally. Here the music is quiet and determined, and the lyrics capture one of the band's persistent themes.
"No Face, No Name, and No Number" ~ Traffic
Well, if anyone could pull it off, it would be Traffic: psychedelic melancholia. Steve Winwood's voice is perfectly counterpointed by the flute as the melotron sets the vibe, creating a tone that is both gorgeous and lost.
"Lush Life" ~ John Coltrane and Johnny Hartman
The greatest version of this classic Billy Strayhorn tune. If there was ever a song for the wee small hours of the morning, when it's too late to be up but too early to go to bed, this is it. Urban down and out romantic lyrics—"I'll live a lush life in some small dive, And there I'll be, while I rot with the rest, Of those whose lives are lonely too."—and a sax break that is instantly recognizable as 'Trane.
"The Song Is Over" ~ The Who
The Who always exude power in their music, and this song is no different. But here the power articulated through the music is self-defeating and sad, and the lyrics, as much about artistic creation as a love affair, swing from proud declarations of intent to a bitter realization of loss. (If this song didn't get mentioned, then "Sunrise", which has one of the most beautiful first lines I've ever heard, would be it.)
"Shipbuilding" ~ Elvis Costello
Written around the time of the British-Argentine war over the Falklands, this song perfectly captures a world-weary cynicism. And the trumpet solo, by the great Chet Baker, is one of the most emotional ever recorded on a rock song.
"Superman's Song" ~ Crash Test Dummies
The music, all cellos and strings, is sad, while the lyrics make you smile. Sure, it's a sad situation they describe, but it's a case of laughing through the tears.
Songs I'm still considering, but haven't made up my mind on yet:
- "I Got the Blues" ~ Rolling Stones ~ The last lines are close: "If you don't believe what I'm singing, At three o'clock in the morning, babe, well, I'm singing my song for you". But that organ break in the middle, while cool as hell … I don't know. Does that ruin the melancholy? Or is more bluesy than melancholy?
- "The Road to Ensenada" ~ Lyle Lovett
- "Flowers of Guatemala" ~ REM ~ Easily Peter Buck's best, most emotional guitar solo.
From a reader
Matthew M. emailed me with this suggestion:
Wanted to share my very very favorite: Wilco's "Someday Soon". Breaks my heart and makes me smile every time.