Post the songs that depress the hell out of you, but still listen to on occasion. Probably when you’re feeling down and just want to wallow in your misery.
I listen to the following songs on a regular basis, but they get a lot more attention from me if I’m feeling sad, even if some of the songs don’t actually have a sad theme.
“Read My Mind” is a great, great song. The Killers are really hit or miss with me, but, man: that one hits on every level.
I tend to gravitate towards sparser stuff when I’m feeling grim. To wit:
The entire Fionna Apple “When the Pawn…” album is probably my favorite album to wallow with. A few tracks on there are serious kicks in the heart.
Springsteen’s “Nebraska” is right there too.
“Red Dirt Girl” (the song, not the album) by Emmylou Harris
“To the Races” (the album AND the song) by Eric Bachmann
Pretty much any Gillian Welch song
Then there’s the entire gamut of admittedly saccharine pop that has struck the right chord with me at various times in my life: “Another Sad Love Song” (Toni Braxton), “I Can’t Make You Love Me” (Bonnie Raitt), “I Hope You Dance” (Leann Womack), and so on. They’re gaudy and over the top but I caught them after a break-up and they made me feel both way happier and way more miserable, as only a really good sad song can.
A lot of Motown songs, strangely, are really sad. Lyrically at least. I had the mistaken idea that they’d cheer me up, but then you hear “Ain’t Too Proud to Beg” and it all goes to shit.
And then, any song or album I bought or was obsessive about during periods of turmoil, regardless of the subject matter, brings back those memories.
Tomorrow Wendy by Concrete Blonde* is one of my favorites.
"Underneath the chilly gray November sky
We can make believe that Kennedy is still alive and
We’re shooting for the moon and smiling Jackie’s driving by and
They say ‘good try’
Tomorrow Wendy’s going to die.
Tomorrow Wendy’s going to die."
There are so many songs in me that won’t be sung,
I feel the bitter taste of tears upon my tongue.
The time has come for me to pay for yesterday when I was young.
And the Band Played Waltzing Mathilda, here performed by the incomparable Ronnie Drew. Cry my fucking eyes out, every time I hear it. Rob Williams of The Fenians also does a spectacular version, especially live.
I would also include Grace, a song about a woman visiting her condemned love in Kilmainham Gaol in Ireland. The link is a partial, sadly- Chris and Rob did a spontaneous a capella version outside the gaol in March of this year, and it took the gal a minute to get her video camera out. Here is a full version performed by The Dubliners.
[ul]
[li]"-1" from Mudvayne’s L.D. 50.[/li][li]“Losing It” from Rush’s “Signals”[/li][li]“Saturn- The Bringer of Old Age” from Gustav Holst’s Planets Suite[/li][li]“She’s Gone” from Black Sabbath’s “Technical Ecstasy”[/li][li]“Epitaph” by King Crimson[/li][/ul]
Big Brother and the Holding Company, Ball and Chain. The greatest blues singer, the greatest bar band, and a song of total hopelessness.
And the Band Played Waltzing Matilda, here by the author. One of the most cutting antiwar songs. Here with some of the poor bastards who fought at Gallipoli.
Funny thing is that George didn’t want to record the song, saying “It’ll never sell. It’s too damned sad!” But he was talked into it, and it completely revitalized his career.
George has wanted to be a rocker since the 50s. I don’t think he’s ever accepted that he’s a balladeer, especially one selling the most depressing ballads imaginable. Being married to Tammy shoulda clued him in, but it didn’t.
A number of Radiohead songs: Fake Plastic Trees, Street Spirit, How To Disappear Completely, Knives Out, You and Whose Army?, Gagging Order
Gilbert O’Sullivan - Alone Again (Naturally)
Conor Obert & Gillian Welch - Lua
Iron & Wine - pretty much any song, but “The Trapeze Swinger” comes to mind first
Des’ree - I’m Kissing You (from Romeo & Juliet - heart-wrenching!)
Band of Horses - The Funeral
That’s just a sampling. Sad songs are some of my favorites, so the list goes on and on.
Radiohead’s ouvre isn’t sunshine and rainbows. Two of my favorite songs of theirs would be Pyramid Song and How to Disappear Completely, which are far from their most depressing.
The other day I heard Gregg Allman’s song Oncoming Traffic for the first time, or at least the first time in so long I’d forgotten it completely. It’s some of the saddest and most clear-eyed writing he ever did, and I’m tempted to say it’s his best song.