The Saddest Rock Songs of All Time, Part I

The greatest ability of a musical performer (musician, singer, composer, etc.) is to make you feel something even when you feel nothing at all. A song will capture you at unawares and unexpectedly steal your senses - sometimes even your heart and soul - and change your whole perspective. You may consider yourself a hard person, as tough as nails, but even so, at one time or another your eyes have watered or perhaps you've even shed a tear when a certain song is playing. That is when music is at its most powerful, and it takes a special gift to render sadness into a musical statement.

Loss, regret, remorse - the things you can't take back but wish you could, even for a moment - are what touch us the most. Sorrow can make you stronger or drag you down to the bitter dregs, but there is a beauty in sorrow, particularly when a musician composes a song about his or her own inner demons - their vulnerabilities, their fears, their loss - and shares it with the world. Sure, some songs are simply manipulative, intended to twist your emotions, but at the heart of most great sad songs is a personal experience, a mournful message that needs to be made to gain closure for the individual.

Oh, for crying out loud! Would you listen to me? I've spent far too long listening to these damn songs and now I am talking like I am a patient for Robert Burton's 1621 classic book The Anatomy of Melancholy, or the full title: The Anatomy of Melancholy, What it is: With all the Kinds, Causes, Symptomes, Prognostickes, and Several Cures of it. In Three Maine Partitions with their several Sections, Members, and Subsections. Philosophically, Medicinally, Historically, Opened and Cut Up (and no,I am not making this up!). In any case, before I start blubbering and get my keyboard wet, here are, in my estimation, fifty of the saddest songs in rock history (with another fifty coming in a future installement - I can only take so many sad songs at once).

The interesting thing about sad rock songs is that they may not have been originally composed to generate tears, but they become sad by association, by melancholy memories or by ironic twists of fate, as is the case of John Lennon's "Imagine" or Nick Drake's "Fruit Tree". Although some of these songs may reflect a personal troubling period in my past, I believe there are enough folks who have been miserable at one time or another that can identify with the songs I've listed.

I could have ventured further and given you Mozart's Requiem Mass in D minor, or a song or two from Frank Sinatra or Billie Holliday, maybe Johnny Cash (whose version of Trent Reznor's "Hurt" is phenomenal) or other country stars boozily wallowing in their pick-up trucks, but the task at hand then becomes too convoluted and the list far too extensive for my patience. Because, as I have mentioned previously, patience is not one of my virtues. In fact, I am not even sure I have any patience. So let's just stick with rock songs. Sad ones. Listed below for your listening edification. Better get yourselves a box or two of Kleenex. And maybe a couple of beers. And call your mom.

Wish You Were Here - Pink Floyd
Written in separate rooms by Gilmour and Waters, the lyrics deal with alienation, the death of Water's grandmother and the loss to drugs and mental disorder of band member Syd Barrett. Perhaps the best song Floyd ever composed.

Time - Alan Parsons Project
The album The Turn of a Friendly Card tells the story of a middle-aged gambler who loses it all. The wistful and whispery ballad of time lost, "Time", marks the first single Eric Woolfson, Alan Parson Project co-founder, sang lead on (and this was their fifth album!).

Eleanor Rigby - The Beatles
A technical and compositional triumph for The Beatles. This McCartney song was shocking at the time of its release due to its unflinching look at loneliness and despair. It also has no semblance of a traditional rock tune, foregoing drums, keyboards and guitar for a double string quartet.

Without You - Harry Nilsson
Originally recorded by the band Badfinger for their album No Dice, Harry Nilsson took the song and brought it to another dimension. The heart-wrenching vocals by Nilsson are a high point in pop-rock balladry.

The Needle and the Damage Done - Neil Young
A song about the evils of heroin addiction that took two of Young's close friends, guitarist Danny Whitten and roadie Bruce Berry. Young recalled, "I am not a preacher, but drugs killed a lot of great men."

Tears in Heaven - Eric Clapton
This about the death of Clapton's four year-old son. It doesn't get anymore poignant than this.

Cats in the Cradle - Harry Chapin
A tale of parental neglect in song form, relating a father's need to succeed in business to the detriment of his growing son. The tragedy comes home when the father realizes his now adult son has turned out to be just like him.

Layla - Derek and the Dominos
The celebrated song of the anguish of unrequited love. "Layla" is in fact Patty Harrison, Beatle George Harrison's wife (George being Clapton's best friend). Patty and George eventually divorced, and Patty married Eric. They also eventually divorced. Such are the strange ways of love.

Time in a Bottle - Jim Croce
"Time in a Bottle" was written by Croce for his infant son, A.J.; unfortunately, Jim Croce died in a plane crash within a year of writing this beautiful tune, making it all the more sad. It did not become a hit until after his death.

Vincent - Don McLean
I don't think any song better encapsulates the artistic triumphs, personal tragedies and tortured mind of an artist better than McLean's ode to Vincent Van Gogh. The lyrics are a beautifully rendered aural painting reflecting Vincent's work.

Landslide - Fleetwood Mac
Stevie Nicks anguished plaint to lost love recorded during her breakup with bandmate Lindsey Buckingham.

Don't Give Up - Peter Gabriel
A great duet between Gabriel and Kate Bush about a despairing man and the attempts of loved ones to save him.

Dust in the Wind - Kansas
One of the most depressing top ten hit songs ever written. The title says it all.

Can't You See - Marshall Tucker Band
One of the greatest country blues tunes ever written.

Me and Bobby McGee - Janis Joplin
There are so many songs sung by Joplin that mirrored the insecurity and sadness of her own life. When she sang, you knew the sentiment was real and window to her personal plight.

Fire and Rain - James Taylor
Taylor fights personal demons and tragedies, the suicide of a childhood friend, drug addiction, the breakup of his band "Flying Machines" and the shock therapy he received while in a mental istitution.

Castles Made of Sand - Jimi Hendrix
A series of sad and ironic stories intertwined in a stream-of-consciousness style with Hendrix's fluid and unmistakable guitar work.

Imagine - John Lennon
I cannot help but getting misty-eyed every time I hear this. That such beautiful and timely sentiment should be silenced by the actions of a crazed fan is the height of irony.

Yesterday - The Beatles
It's hard to imagine Paul being sad about anything at that time in his life. But even from a cynical standpoint, McCartney's ability to pull at our heartstrings is amazing.

I’m Not in Love - 10CC
A song about a man who is pretending not to be miserable. He is not very convincing in that regard.

Mother - John Lennon
Lennon's anguish over the loss of his mother and the abandonment by his father are palpable. The screaming at the end is part of Lennon's "primal therapy" that he underwent previous to recording this song.

Ticking - Elton John
One of the greatest studies of a troubled mind ever recorded. The subject matter is intense but still moving and brilliant.

While My Guitar Gently Weeps - The Beatles
The Love album acoustic version of this George Harrison song is given greater pathos with strings added by George Martin and an extra stanza of verse by Harrison that didn't make it onto the original White Album recording.

Tempted - Squeeze
Infidelity is infectious with the Motown groove of this Squeeze song. One of the best songs recorded in the misbegotten 80s.

Operator - Jim Croce
Some of you younger folks may not have ever used a pay telephone, but you may have seen a phone booth or two in the movies. The line "you can keep the dime" refers to the cost of a phone call back in the dark ages.

Candle in the Wind - Elton John
A poignant homage to Marilyn Monroe which Sir Elton eventually rewrote to cover Princess Diana's death as well. Who knows how many deaths Elton can cover with this song.

The Sounds of Silence - Simon & Garfunkel
Here's the original version without the electric guitar. Great song of societal upheaval and the silent howl of the voiceless masses.

Behind Blue Eyes - The Who
A song of anger and unfulfilled hopes. And no, Limp Bizkit didn't write this goddamned song! They couldn't even sing it.

Time - Pink Floyd
A great song of regret over time wasted and youth frittered away. Of work never done and objectives never accomplished.

Hallelujah - Jeff Buckley
I used this version of this song rather than the original Leonard Cohen recording because Buckley's beautiful rendition is poignant and moreso since he died so young.

With or Without You - U2
The paradox of love gone bad, where you can't stand to be with a person, but can't stand to be apart. What a crappy feeling.

Thorn Tree in the Garden - Derek and the Dominos
While Eric Clapton and Duane Allman got most of the adulation for their contributions to Derek and the Dominos, Bobby Whitlock's rueful song and plaintive vocals are one of the highlights of the album.

How Can I Tell You - Cat Stevens
Unrequited love, or love unspoken: one of the most endearing subjects for lovelorn poets. Like Cat, for instance.

Leaving on a Jet Plane - Peter, Paul & Mary
Leaving is the hardest part, isn't it?

The River - Bruce Springsteen
More powerful than the trite "Born in the USA". Bruce's populist appeal goes beyond simple patriotic sentiment to real dreams and hopes crushed by life in this song.

America - Simon & Garfunkel
A wistful and remorseful visit to the disillusionment that filled many of the generation that grew to adulthood during the Vietnam War.

Alone Again, Naturally - Gilbert O. Sullivan
A pure piece of pop that reaches beyond pretense for actual heart-rending reflection.

To The Last Whale (Critical Mass and Wind on the Water) - Crosby & Nash
A powerful song of Man's inhumanity and the senseless waste of beautiful and intelligent creatures for our petty pleasures. That's James Taylor singing background at the end of the song.

Jeremy - Pearl Jam
One of the few MTV videos that actually affected me when I first saw it (I didn't include the video here, just the lyrics). A reflection of many of the lost teens who kill themselves or others and appear with alarming regularity on the evening news.

Iris - Goo Goo Dolls
I like the guitar, 5 of 6 strings tuned to D. Oh yeah, the song is certainly sad as well.

Who Wants to Live Forever - Queen
A very moving song from Queen that I recall fondly from the great cult classic The Highlander, and a reminder that many Queen songs may be immortal, but not so Freddie Mercury.

My Immortal - Evanescence
An infinitely sad song Amy Lee wrote to her dead sister. That's all I have to say about that.

One and Only - The Young Dubliners
One of the greatest songs you never heard. This troubling song deals with incest and the dysfunction of parents that refuse to listen or help a daughter in anguish.

Don't Let It Bring You Down - Neil Young
Okay, I can offer up whole albums of sad Neil Young songs, but this one is a particular favorite. I love the stark lyrics.

Crash-Barrier Waltzer - Jethro Tull
A regretful man tries to aid an old drunk to ease his own conscience, but harsh reality in the form of a cynical policeman gets in the way.

Daylight Again/Find the Cost of Freedom - Crosby, Stills & Nash
A stunning anti-war protest from CS&N that deals more with the dead than the living.

Fruit Tree - Nick Drake
Death hung from Nick like the moss on old oak. And he was old when he was very young, and he was too soon gone and his fame came just as this song predicted.

There's Always Something There to Remind Me - Naked Eyes
Yes, this song is hopelessly lost in the 80s with its drum machines and synths, but millions mourned their loves lost over this tune by a band no one remembers.

4 + 20 - Stephen Stills
A song of utter desperation found on CSN&Y's Déjà Vu album, but which is completely a Stephen Stills production and composition.

Irene Wilde - Ian Hunter
A true story according to Ian Hunter, documenting the bittersweet teenage angst and unrequited love that we all go through. Well, at least I did. Thanks for that one, Ian.