This is the first post I’ve made on the Joyous Crybaby blog in close to a decade—but I knew I was letting it hang around for some reason. Today I have one, which is that my friend Lou Mindar posted his own 25 Saddest Songs list and asked for other such songs/lists. Not that I’m reviving Joyous Crybaby, but it seems like an easy place to make a kinda large list like this and it perfectly aligns with the Joyous Crybaby theme. Sad songs are, of course, sad, but they are also beautiful and beloved. Back in the day, I kept a page of Songs That Make US Cry, and many of these first appeared there.
I haven’t tried to put these in rank order, and I haven’t had time to write up the kind of thoughtful commentaries that Lou included in his list. Rather, I’ve treated these more like a play list, attempting at least a little to include contrasts and transitions and echoes through the list. Like an old mix tape, which it’s clear is my era. I’m self-conscious about how this list reflects that era and my age. I tried to fit in a couple of more recent things, but, really, they just weren’t as emotional for me. And it’s also true that I have not kept up with popular music much since about 2000, not because of a lack of interest so much as overwork and other stuff that goes with it. I’m trying to retrieve myself these days, so I do things like pause and make a sad songs list. Thanks to Lou for the inspiration.
This list goes slightly over 25—with two songs by Joe Jackson’s great double album Big World, two arias because I couldn’t decide which was sadder, and a couple of extras at the end, so really a total of 29 songs, all of which are more or less sad. I felt it important to include some angry-sad songs in addition to the wistful-sad ones, and, of course, sadness often carries at least a tinge of hope. A few other songs came really close but didn’t make it to this final list: REM’s “Everybody Hurts,” The Who’s “Behind Blue Eyes,” Melissa Etheridge’s “Breathe,” and Neil Young’s “Old Man.”
Enjoy! Weep!
1. Paradise
Written and performed by John Prine
2. Pretty Bird
Written by Hazel Dickens
Performed a capella by Hazel Dickens on the album Hazel & Alice [Gerrard]
3. The Boxer
Written by Paul Simon
Performed by Simon & Garfunkel
4. Love Has No Pride
Written by Eric Justin Kaz and Libby Titus
Performed by Bonnie Raitt
5. Rainy Night in Georgia
Written by Tony Joe White
Performed by Brook Benton
6. a. Shanghai Sky and 6. b. We Can’t Live Together
Written and performed by Joe Jackson
7. Eleanor Rigby
Written by Paul McCartney and John Lennon
Performed by The Beatles
8. Backwater Blues
Written and performed by Bessie Smith
9. Nocturne, B. 49: Lento con gran espressione in C-sharp minor
Written by Frederic Chopin
Performed by Janusz Olejniczak
10. Little Green
Written and performed by Joni Mitchell
11. Fast Car
Written and performed by Tracy Chapman
12. Death Song
Traditional song arranged and performed by R. Carlos Nakai
13. Redemption Song
Written and performed by Bob Marley
14. Wish You Were Here
Written by David Gilmour and Roger Waters
Performed by Pink Floyd
15. Asimbonanga (Mandela)
Written by Johnny Clegg
Performed by Johnny Clegg and Savuka
16. Crime for Crime
Written and performed by Ani DiFranco
17. Hang Down Your Head
Written by Tom Waits and Kathleen Brennan
Performed by Tom Waits
18. I Loved a Lass
Traditional arranged by Terry Cox, Bert Jansch, Jacqui McShee, John Renbourn, Danny Thompson
Performed by The Pentangle
19. Devil Song
Written and performed by Beth Orton
20. Killing Me Softly
Written by Charles Fox and Norman Gimbel
Performed by Roberta Flack
21. With or Without You
Written by Bono and U2
Performed by U2
22 a. and b. I could not choose which of these was sadder, so feel free to pick one or listen to both.
Un bel di (from Madame Butterfly)
Written by Giacomo Puccini
Performed by Leontyne Price and the Orchestra de Radio-Canada and Jacques Beaudry
Ebben? Ne andrò lontana (from La Wally)
Written by Alfredo Catalani
Performed by Angela Gheorghiu and the Royal Philharmonic Orchestra and Marco Armiliato
23. Mona Lisas and Mad Hatters
Written and performed by Elton John
24. Me and Bobby McGee
Written by Kris Kristofferson
Performed by Janis Joplin
25. Blowin’ in the Wind
Written by Bob Dylan
Performed by Bob Dylan
Performed by Peter, Paul, and Mary
26. Gone for Good
Written by Mark Sandman, Dana Colley, and Billy Conway
Performed by Morphine
PostScript. The Lark Ascending
Written by Ralph Vaughn-Williams
Performed by Hilary Hahn with the London Symphony Orchestra and Sir Colin Davis
Lisa Roney
Joyous Crybaby 