Sad Bastard Music
A Playlist for the Broken Hearted
Music
A Playlist for the Broken Hearted
Sometimes when I am a bit bummed, I don’t look for music to lift me up; I look for music that captures my mood. For some reason, I find solace in listening to songs from my sad bastard brethren.
Losing someone you love in any capacity is gutting. These songs capture those feelings of loss and/or hurt.
And each of these songs is a musical testament to loss.
And each of these songs continues to deepen its roots in my emotional psyche. And each of these songs I never get tired of hearing.
Now you may notice the songs on the playlist below are predominantly about heartaches and hearts breaking. It is, sadly, familiar ground for many of us.
This isn’t meant to be a definitive list, obviously. Everyone has their own favorites (leave a comment, let me know yours). I tweaked this playlist down to about 90 minutes.
Now, if you’re of a certain age, you will recall 90 minutes is the length of a mixtape. And if you remember that, I bet you remember making a mixtape for OR about the person who broke your heart.
SIDE ONE
“Silver Springs” — Fleetwood Mac
This is a song that was recorded for Rumours but didn’t make it on the record (obviously). But the reason is nerdily interesting.
I found out when I read Making Rumours: The Inside Story of the Classic Fleetwood Mac Album by producer/engineer Ken Caillat that vinyl records at the time could only have 22 minutes per side. The original recorded version clocked in at over eight minutes, meaning that “Silver Springs” would take the place of two songs. Caillat and Stevie Nicks eventually got the song to 4:33, but it would end up as a b-side until it was released properly on 1997’s The Dance.
“Time cast a spell on you but you won’t forget me
I know I could’ve loved you, but you would not let me
I’ll follow you down ’til the sound of my voice will haunt you”
“If You See Her, Say Hello” — Bob Dylan
This track is from Dylan’s pièce de résistance, Blood on the Tracks. For my money, this is about as flawless as a heartbreak album could ever be. This record is like a musical version of Ingmar Bergman’s Scenes From A Marriage.
“And though our separation
It pierced me to the heart
She still lives inside of me
We’ve never been apart”
“Houses on the Hill” — Whiskeytown
Whiskeytown was more than the sum of its parts. Ryan Adams was the singer and songwriter, yes. He was also a notorious asshole …and assholes always get called out, as we saw.
This song from Strangers Almanac, a flawless record, just like Rumours and Blood on the Tracks, is a 2:38 movie. Close your eyes and listen, and you can see a man crawling around the attic opening boxes until he discovers a “bunch of letters written for the fella who broke your momma’s heart.”
Ryan Adams may have been the singer and songwriter, but Whiskeytown was the band.
“Eisenhower sent him to war
He kept her picture in his pocket that was closest to his heart
And when he hit shore
Must have been a target for the gunman”
“Unsatisfied” — The Replacements
There will invariably be a song by The Replacements on almost any mix or playlist I make. Deal with it. This song, off of 1984’s Let it Be (another flawless album), is a brutal song about a relationship going down the shitter. This song is about as far from “Gary’s Got A Boner” as you can imagine.
And unless you married your first boyfriend/girlfriend, you’ve experienced this. And it hurts like hell.
“Look me in the eye
And tell me that I’m satisfied
Were you satisfied?
Look me in the eye
Then, tell me that I’m satisfied
And now are you satisfied?”
“Whiskey Bottle” — Uncle Tupelo
A band that once opened for The Replacements, Uncle Tupelo existed for just a short time but shaped much of what we call Americana today. Off the band’s debut, No Depression, this is all you need to know about this song:
“A long way from happiness
In a three hour away town
Whiskey bottle over Jesus
Not forever, just for now”
“You Don’t Have To Say You Love Me” — Shelby Lynne
This is off Lynne’s tribute album to Dusty Springfield, Just a Little Lovin’. Have you ever tried to hold on to someone who wanted to leave you? What you learn are two things. One, your threshold for emotional masochism is much higher than you think, and two, it’s futile.
“You don’t have to say you love me just be close at hand
You don’t have to stay forever I will understand
Believe me, believe me, I can’t help but love you
But believe me, I’ll never tie you down
Left alone with just a memory
Life seems dead and quite unreal
All that’s left is loneliness there’s nothing left to feel”
“A Murder of One” — Counting Crows
Despite their commercial popularity, Counting Crows have always been a maligned band, and that’s unfair. This is a band in the classic sense of a band; the lead singer writes (amazingly) and sings and is backed by incredible musicians. I dunno; I’ve just never understood why people rag on them.
Their debut, August and Everything After, is loaded with allegory and literary context, and “A Murder of One” still stands out.
Singer Adam Duritz explains its meaning: “But life ends up being so much less than we thought it would be when we were kids, with relationships that are so empty and stupid and brutal. If you don’t find a way to break the chain and change in some way, then you wind up, as the rhyme goes: a murder of one, for sorrow.”
“Are you happy where you’re sleeping?
Does he keep you safe and warm?
Does he tell you when you’re sorry?
Does he tell you when you’re wrong?”
“Free” — Train
Before they were a poptastic platinum band, Train actually had a little edge to them. This isn’t the song that people noticed first; that was “Meet Virginia,” but it should’ve been. There’s no deep meaning here, just a good song about loss, regret, dreams, and moving on.
“Staring at the dark again, you left your silhouette upon my pillow”
“I’d Rather Go Blind” — Etta James
Etta James is an artist that sure did some livin’ and some lovin’. And you can hear it in every song she sings. Etta James was one of the few who could glide from genre to genre effortlessly. This song is a kissing cousin to “You Don’t Have to Say You Love Me.”
“Whoo and baby, baby, I’d rather, I’d rather be blind, boy
Then to see you walk away, see you walk away from me, yeah”
“Hello It’s Me” — Todd Rundgren
Todd Rundgren is about as about as iconoclastic as a musician as you can find. He was one of the first to sketch out the blueprint that a modern artist didn’t need to be pigeonholed as this or that. A musician could be a songwriter, musician, engineer, producer, bandleader, and visionary.
And excel at all of them.
And long before drunk texting, there was drunk dialing.
And we all did it.
“I take for granted that you’re always there,
I take for granted that you just don’t care,
Sometimes I can’t help seeing all the way through.
It’s important to me
That you know you are free”
SIDE TWO
“Last Goodbye” — Jeff Buckley
Jeff Buckley’s story is just one of music’s tragedies. What makes his life interesting is his pedigree and the fact that he may have died being reckless; it wasn’t a result of drugs or alcohol. It even spawned two Hollywood movies.
This song is from his only proper studio album, 1994’s Grace, an album that has been a slow burner for the past 22 years.
“The Last Goodbye” was the album’s second single and actually scored Buckley a minor “Alternative” (whatever that means) hit in 1995.
This song still gets me. Not only does it sound modern, but its message is timeless. Closure in the collapse of a relationship is seldom achieved, and even when it is, if it was real love, the feelings never die.
“This is our last embrace
Must I dream and always see your face?
Why can’t we overcome this wall?
Baby, maybe it's just because you didn’t know you at all”
“The Ghost in You” — The Psychedelic Furs
The Furs were part of the “New Wave” or “New Romantic” movement of the late-70s/early ’80s that gave us Duran Duran, Roxy Music, and The Human League.
The Psychedelic Furs first impact in the US came when they hired none other than Todd Rundgren (see above) to produce their album, Forever Now. That album gave the Furs a modest hit with “Love My Way.” Of course, their song “Pretty in Pink” was the inspiration for the John Hughes movie.
Have you ever been in love, and while the relationship may have died, the person still lives in you? Like a ghost? Yea, me too.
“The ghost in you
She don’t fade
Inside you, the time moves
And she don’t fade”
“When You’re Alone” — Bruce Springsteen
From Bruce Springsteen’s Tunnel of Love, his own Blood on the Tracks. That may be apples to oranges comparison, but conceptually, they’re both about the collapse of a marriage. And since 1987's Tunnel of Love was released, we’ve come to learn more about Springsteen’s personal demons, making this particular song carry more weight all these years later. It’s the rare artist who can create something that gains depth as it gets older. Springsteen is one of those.
“Times were tough love was not enough
So you said sorry Johnny I’m gone gone gone
You said my act was funny
But we both knew what was missing honey”
“Dust” — Lucinda Williams
For my money, Lucinda Williams is uncategorizable. She is a multi-hyphenate: singer, songwriter, guitar player, poet, and producer. First and foremost, Williams is an artist. What sets her work apart from some of her contemporaries is that her songs often have a literary quality.
But this song wasn’t written by her, but by her father, Miller Williams, a famous poet. That’s no easy task in the world of poetry. However, Miller Williams is probably best known for reading a poem at the second inauguration of Bill Clinton.
The music for “Dust” was written and arranged by Lucinda. The result is the perfect blend of poetry and music.
“It’s a sadness so deep the sun seems black
And you don’t have to try to keep the tears back
No, you don’t have to try to keep the tears back
’Cause you couldn’t cry if you wanted to
You couldn’t cry if you wanted to
Couldn’t cry if you wanted to
You couldn’t cry if you wanted to
Even your thoughts are dust”
“Someone Else” — Emitt Rhodes
Emitt Rhodes is one of those musicians that had everything in him and behind him but didn’t reach a wide audience. He was always a critic’s darling, but historically that seldom translates into huge record sales. Naturally, his career was sidelined by strife with his label, and by the 1980s, he’d more or less stopped recording.
Rhodes re-emerged after his song “Lullabye” was used in Wes Anderson’s The Royal Tenenbaums; he got back to the studio and began recording again.
There is a film about Rhodes, presumably still unreleased, titled The One Man Beatles …seems like a fair title.
“You like her so much it makes you sick
And you just can’t make no sense of it
You can’t say yes, but you can’t say no
It’s for you to guess, for her to know”
“Time After Time” — Eva Cassidy
Originally a hit for Cyndi Lauper, Eva Cassidy took it and completely made it her own.
The life of Eva Cassidy is a tragedy in the largest sense. She died in 1996 of Melanoma before she had a chance to reach a larger audience. But her posthumous albums have charted in the top ten worldwide and have sold more than ten million copies. Her death meant her family lost a daughter, sibling, cousin, etc., and the music world lost an extraordinary talent.
“Lying in my bed, I hear the clock tick and think of you
Caught up in circles
Confusion is nothing new
Flashback, warm nights
Almost left behind
Suitcase of memories”
“Blue” — The Jayhawks
The second band from Minneapolis on this playlist, The Jayhawks, helped shepherd the Alt-Country genre in the ’90s. The story of The Jayhawks reads like so many others in music — great band and great songwriters (Gary Louris, Marc Olsen) pair with great producers (Bob Ezrin, George Drakoulias) and make great albums (two being Hollywood Town Hall and Tomorrow the Green Grass)…that don’t really reach the level of success worthy of the talent and the work. That happens a lot in the arts.
This line from “Blue,” the first song on the critically acclaimed Tomorrow the Green Grass, can sum up the band’s career just as easily as it sums up the collapse of a love affair.
“It’s hard to sing with someone
Who won’t sing with you”
“Your Heart Is As Black As Night” — Melody Gardot
I don’t think this requires too much to be said.
“Your lips may be sweet
Such that I can’t compete
But your heart is as black as night”
“A Case of You” — Joni Mitchell
This is from Joni Mitchell’s album, Blue. The album chronicles the collapse of her relationship first with Graham Nash (yea, the N is CSN) and then James Taylor (yep, that one). The songs are so personal and powerful that when Kris Kristofferson first heard Blue, he allegedly commented, “Joni! Keep something to yourself!”
Almost every music critic considers Blue to be one of the greatest albums of all time, and The New York Times chose Blue as one of the 25 albums that represented “turning points and pinnacles in 20th-century popular music”.
Joni Mitchell has said that “A Case of You” deals with the collapse of her relationship with Nash.
“Oh, you’re in my blood like holy wine
You taste so bitter and so sweet.
Oh, I could drink a case of you, darling
And still I’d be on my feet
I would still be on my feet”
“Who Am I To You” — Schuyler Fisk
Schuyler Fisk has had to live in the shadow of her Academy Award-winning mother, Sissy Spacek. Luckily for Fisk, she is as talented a songwriter as her mother is an actress and her father, Academy Award-nominated production designer and director Jack Fisk.
Fisk’s 2009 full-length debut, The Good Stuff, proved she definitely inherited her parents' creative gene. Pigeonholed as a “folk” record, the album garnered good reviews but didn’t do a whole lot commercially. For what it's worth, The Good Stuff is as “folk” as Rumours. The album's songs are evidence that Fisk had certainly been in love a time or two.
In fact, she may have even wondered about the status of a relationship.
“If it’s not me you need
To sleep beside
If I’m not the thought that’s always on your mind
If I’m not the reason why you dream at night
The love you’ll never lose
Then who am I to you?”
“When Ye Go Away” — The Waterboys
In the morning you’ll be following your trail again
Fair lady
You ain’t calling me to join you
And I’m spoken for anyway
But I will cry when ye go away
I will cry when ye go away
**WARNING: SOME OF THESE SONGS ARE SAD AF.**