25 More of the Saddest Songs Ever Written (Volume 2)

In November of last year, I share the 25 saddest songs I had ever heard. Granted, I haven’t heard all sad songs. In fact, there are entire genres I am unfamiliar with. So, let me stipulate up front that these lists are just my opinion and that my purview is not only subjective, but very limited.

When I wrote my first list of the 25 saddest songs ever written, I actually was working from a list of more than 75 sad songs. I picked 25 at random, but the songs on this list (and the forthcoming volume 3 of the list) are just as deserving of recognition.  Accordingly, here are 25 more sad songs for your consideration. Listen to a few tonight and cry yourself to sleep.

26. Missing You
Written by: John Waite, Mark Leonard, & Charles Stanford
Performed by: John Waite

“Missing You” came out in July 1984. If I saw it once on MTV, I saw it a thousand times. (For readers under 50 years of age, MTV got its start playing nothing but music videos. It started a revolution in the music industry, matching a video with a song. It became so popular that some musicians conceived of the video before creating the song. It was a simpler time.) Although I like the John Waite video for the song, I look for reasons to watch and listen to Allison Krauss. So, here’s Allison Krauss and John Waite doing a duet of “Missing You.”

Missing You

Every time I think of you
I always catch my breath
And I’m still standing here
And you’re miles away
And I’m wondering why you left
And there’s a storm that’s raging
Through my frozen heart tonight

I hear your name in certain circles
And it always makes me smile
I spend my time
Thinking about you
And it’s almost driving me wild
And that’s my heart that’s breaking
Down this long distance line tonight

I ain’t missing you at all
Since you’ve been gone away
I ain’t missing you
No matter
What my friends say

There’s a message in the wild
And I’m sending you this signal tonight
You don’t know how desperate I’ve become
And it looks like I’m losing this fight

In your world I have no meaning
Though I’m trying hard to understand
And it’s my heart that’s breaking
Down this long distance line tonight

But I ain’t missing you at all
Since you’ve been gone away
I ain’t missing you
No matter what I might say

And there’s a message that I’m sending out
Like a telegraph to your soul
And if I can’t bridge this distance
Stop this heartbreak overload

‘Cause I ain’t missing you at all
Since you’ve been gone away
I ain’t missing you
No matter what I might say

I ain’t missing you (I ain’t missing you)
No way
Since you’ve been gone away (I can lie to myself these days)
I ain’t missing you

And there’s a storm that’s raging
Through my frozen heart tonight

And I ain’t missing you at all
Since you’ve been gone away
I ain’t missing you
No matter what my friends say

I ain’t missing you
I ain’t missing you (I can lie to myself these days)
I ain’t missing you at all, I ain’t missing you (No way, baby)

No matter what my friends say (I’m doing fine here)
And I ain’t missing you at all
I ain’t missing you
I keep lying to myself every time I think of you

I’m okay
I’m doing fine here from day to day
I ain’t missing you
I can lie to myself

27.  Wreck of the Edmund Fitzgerald
Written by Gordon Lightfoot
Performed by: Gordon Lightfoot

“Does any one know where the love of God goesWhen the waves turn the minutes to hours?”

In November 1975, I was fifteen years old. That’s probably a little old to develop irrational fears, yet that’s exactly what happened to me. In that month and year, I became afraid of Lake Superior (“the big lake they call Gitche Gumee”). Why? That’s the month the U.S.S. Edmund Fitzgerald sank in Lake Superior, taking with it twenty-nine souls.

I grew up near Chicago and was fairly accustomed to being around Lake Michigan. But where Lake Michigan seemed fun and inviting, Lake Superior seemed frightening, a place to avoid. Like I said, it was an irrational fear. Thankfully, I’m almost over it.

Wreck of the Edmund Fitzgerald

The legend lives on from the Chippewa on downOf the big lake they call Gitche GumeeThe lake, it is said, never gives up her deadWhen the skies of November turn gloomy
With a load of iron ore twenty-six thousand tons moreThan the Edmund Fitzgerald weighed emptyThat good ship and true was a bone to be chewedWhen the gales of November came early
The ship was the pride of the American sideComing back from some mill in WisconsinAs the big freighters go, it was bigger than mostWith a crew and good captain well seasoned
Concluding some terms with a couple of steel firmsWhen they left fully loaded for ClevelandAnd later that night when the ship’s bell rangCould it be the north wind they’d been feelin’?
The wind in the wires made a tattle-tale soundAnd a wave broke over the railingAnd every man knew, as the captain did tooT’was the witch of November come stealin’
The dawn came late and the breakfast had to waitWhen the gales of November came slashin’When afternoon came it was freezin’ rainIn the face of a hurricane west wind
When suppertime came, the old cook came on deck sayin’“Fellas, it’s too rough to feed ya”At 7 PM, a main hatchway caved in, he said“Fellas, it’s been good to know ya”
The captain wired in he had water comin’ inAnd the good ship and crew was in perilAnd later that night when his lights went outta sightCame the wreck of the Edmund Fitzgerald
Does any one know where the love of God goesWhen the waves turn the minutes to hours?The searchers all say they’d have made Whitefish BayIf they’d put fifteen more miles behind her
They might have split up or they might have capsizedThey may have broke deep and took waterAnd all that remains is the faces and the namesOf the wives and the sons and the daughters
Lake Huron rolls, Superior singsIn the rooms of her ice-water mansionOld Michigan steams like a young man’s dreamsThe islands and bays are for sportsmen
And farther below Lake OntarioTakes in what Lake Erie can send herAnd the iron boats go as the mariners all knowWith the gales of November remembered
In a musty old hall in Detroit they prayedIn the maritime sailors’ cathedralThe church bell chimed ’til it rang twenty-nine timesFor each man on the Edmund Fitzgerald
The legend lives on from the Chippewa on downOf the big lake they call Gitche GumeeSuperior, they said, never gives up her deadWhen the gales of November come early

28. I Can’t Make You Love Me
Written by: Mike Reid and Allen Shamblin
Performed by: Bonnie Raitt

I love the story behind the writing of “I Can’t Make You Love Me.” Like many good songwriters, Allen Shamblin was born in Nashville and Mike Reid played in the NFL. Wait…what? That’s right. Before becoming a successful songwriter, Mike played college football at Penn State. He was so good, he finished fifth in Heisman Trophy voting as an offensive lineman. He went on to become a first round pick in the NFL draft, going to the Cincinnati Bengals. He also played gangster Big Julie in the Penn State production of Guys and Dolls. Mike Reid was nothing if not versatile.

“I Can’t Make You Love Me” tells the heartbreaking story of a guy (or in Bonnie Raitt’s singing, a girl) who is losing the person he loves. They spend one more night together and he tells her “Morning will come, and I’ll do what’s right. Just give me ’til then to give up this fight.” I’m starting to get weepy just thinking about it.

I Can’t Make You Love Me

Turn down the lights
Turn down the bed
Turn down these voices inside my head
Lay down with me
Tell me no lies
Just hold me close, don’t patronize
Don’t patronize me‘Cause I can’t make you love me if you don’t
You can’t make your heart feel something it won’t
Here in the dark, in these final hours
I will lay down my heart and I’ll feel the power
But you won’t, no you won’t
‘Cause I can’t make you love me, if you don’t

I’ll close my eyes, then I won’t see
The love you don’t feel when you’re holding me
Morning will come and I’ll do what’s right
Just give me till then to give up this fight
And I will give up this fight

‘Cause I can’t make you love me if you don’t
You can’t make your heart feel something it won’t
Here in the dark, in these final hours
I will lay down my heart and I’ll feel the power
But you won’t, no you won’t
‘Cause I can’t make you love me, if you don’t

29. For The Good Times
Written By: Kris Kristofferson
Performed by: Johnny Cash (among others)

I love Kris Kristofferson’s story. He was an Army brat who moved around a lot. He attended Pomona College, where he played football, rugby, and ran track & field. Upon graduation from Pomona, he attended University of Oxford on a Rhodes Scholarship (that’s a big deal), While at Oxford, he played rugby and was on the boxing team. It was also at Oxford where he started writing songs, playing guitar, and singing.

Before pursuing a full-time music career, Kristofferson joined the Army, became a helicopter pilot, and rose to the rank of captain. In 1965, he started spending time in Nashville where he tried to sell his songs. He gave a demo tape to June Carter, wife of Johnny Cash, and asked her to give the tape to the popular Cash. She did, but Cash threw it on a pile with other demos and ignored it.

After not hearing from Cash for some time, Kristofferson flew a helicopter to Cash’s house and landed on his front lawn. That got Cash’s attention, and the rest is history. Kristofferson went on to become a successful songwriter (winning Songwriter of the Year in 1970), singer (recording 17 albums), and actor. He also went on to sit across the aisle from me at the premier of his film, Bloodworth. He does not tell that story nearly as often as I do. We did not speak.

For the Good Times

Don’t look so sad, I know it’s over
But life goes on and this old world will keep on turning
Let’s just be glad we had some time to spend together
There’s no need to watch the bridges that we’re burning

Lay your head upon my pillow
Hold your warm and tender body close to mine
Hear the whisper of the raindrops blowin’ soft against the window
And make-believe you love me one more time
For the good times

I’ll get along, you’ll find another
And I’ll be here if you should find you ever need me
Don’t say a word about tomorrow or forever
There’ll be time enough for sadness when you leave me

Lay your head upon my pillow
Hold your warm and tender body close to mine
Hear the whisper of the raindrops blowin’ soft against the window
And make-believe you love me one more time
For the good times

30. Eleanor Rigby
Written By: Paul McCartney and John Lennon
Performed by: The Beatles

I once heard Paul McCartney talk about how he came up with the song “Eleanor Rigby.” In a nutshell, he wanted to tell a story about the lives of lonely people. He came up with Eleanor Rigby (who began life as Daisy Hawkins), an old-maid type woman, and Father McKenzie (who began life as Father McCartney), a church vicar who presides over a small congregation of lonely people. It really brought home for me how sad the song really is.

Eleanor Rigby

Ah, look at all the lonely people
Ah, look at all the lonely people

Eleanor Rigby picks up the rice in the church where a wedding has been
Lives in a dream
Waits at the window, wearing the face that she keeps in a jar by the door
Who is it for?

All the lonely people
Where do they all come from?
All the lonely people
Where do they all belong?

Father McKenzie writing the words of a sermon that no one will hear
No one comes near
Look at him working, darning his socks in the night when there’s nobody there
What does he care?

All the lonely people
Where do they all come from?
All the lonely people
Where do they all belong?

Ah, look at all the lonely people
Ah, look at all the lonely people

Eleanor Rigby died in the church and was buried along with her name
Nobody came
Father McKenzie wiping the dirt from his hands as he walks from the grave
No one was saved

All the lonely people
(Ah, look at all the lonely people)
Where do they all come from?
All the lonely people
(Ah, look at all the lonely people)
Where do they all belong?

31. Crying
Written by Roy Orbison
Performed by Roy Orbison

It stands to reason that a song called “Crying” should be sad. It helps that Roy Orbison’s multi-octave voice is on full displaying in the song. I think it was “Crying” that Bruce Springsteen (a big fan of Orbison’s) was singing about in “Thunder Road” when he sang “Roy Orbison singing for the lonely. Hey, that’s me and I want you only.” If it’s good enough for Bruce, it’s good enough for me.

Crying

I was all right for awhile
I could smile for awhile
But I saw you last night
You held my hand so tight
As you stopped to say, “Hello”
Oh, you wished me well
You, you couldn’t tell
That I’d been crying over you
Crying over you
When you said, “So long”
Left me standing all alone
Alone and crying, crying
Crying, crying
It’s hard to understand
But the touch of your hand
Can start me crying
I thought that I was over you
But it’s true, so true
I love you even more
Than I did before
But, darling, what can I do?
For you don’t love me
And I’ll always be crying over you
Crying over you
Yes, now you’re gone
And from this moment on
I’ll be crying, crying
Crying, crying
Yeah, crying, crying
Over you

32. Atlantic City
Written by Bruce Springsteen
Performed by Bruce Springsteen

In 1981, Bruce Springsteen started recording songs for his solo album (i.e. without The E Street Band), Nebraska. He was sitting in his home studio (i.e. his bedroom) working on a song that was then titled “Fist Full of Dollars,” a homage of sorts to Clint Eastwood’s movie of the same name. Eventually, the song became “Atlantic City.” Like most of the rest of the Nebraska album, “Atlantic City” is pared down, spare, and gritty. There’s nothing pretty about it, and you have to look pretty hard to find anything that’s hopeful. Bruce Springsteen can really write a sad song.

Atlantic City

Well, they blew up the chicken man in Philly last night
And they blew up his house, too
Down on the boardwalk, they’re getting ready for a fight
Gonna see what them racket boys can do
Now there’s trouble busing in from out of state
And the D.A. can’t get no relief
Gonna be a rumble out on the promenade
And the gambling commission’s hanging on by the skin of its teeth

Well, now, everything dies, baby, that’s a fact
But maybe everything that dies someday comes back
Put your makeup on, fix your hair up pretty
And meet me tonight in Atlantic City

Well, I got a job and tried to put my money away
But I got debts that no honest man can pay
So I drew what I had from the Central Trust
And I bought us two tickets on that Coast City bus

Well, now, everything dies, baby, that’s a fact
But maybe everything that dies someday comes back
Put your makeup on, fix your hair up pretty
And meet me tonight in Atlantic City

Now, our luck may have died, and our love may be cold
But with you, forever, I’ll stay
We’re going out where the sand’s turning to gold
So put on your stockings, baby, ’cause the night’s getting cold

And everything dies, baby, that’s a fact
But maybe everything that dies someday comes back

Now I been looking for a job, but it’s hard to find
Down here, it’s just winners and losers and “Don’t get caught on the wrong side of that line”
Well, I’m tired of coming out on the losing end
So, honey, last night, I met this guy, and I’m gonna do a little favor for him

Well, now, everything dies, baby, that’s a fact
But maybe everything that dies someday comes back
Put your makeup on, fix your hair up pretty
And meet me tonight in Atlantic City

33. Dancing in the Dark
Written by: Bruce Springsteen
Performed by: Bruce Springsteen/Sam Fender

It’s a Springsteen two-for!

If you’re of a certain age, you probably remember the video for Springsteen’s Dancing in the Dark. It’s upbeat, and Bruce is looking buff, dancing around the stage. As you may know, this is the song where a not-yet-famous Courtney Cox (of Friends fame) comes up on stage and dances with the Boss. It seems like a celebration.

But listen to the lyrics. They tell a very different story. In addition to the Boss’s version, here’s Sam Fender reimagining Springsteen’s song. Do your best not to cry.

Dancing in the Dark

I get up in the evening
And I ain’t got nothing to say
I come home in the morning
I go to bed feeling the same way

I ain’t nothing but tired
Man, I’m just tired and bored with myself
Hey there baby, I could use just a little help
You can’t start a fire
You can’t start a fire without a spark
This gun’s for hire
Even if we’re just dancing in the dark

Message keeps getting clearer
Radio’s on and I’m moving ’round the place
I check my look in the mirror
I wanna change my clothes, my hair, my face

Man, I ain’t getting nowhere
I’m just living in a dump like this
There’s something happening somewhere
Baby, I just know that there is

You can’t start a fire
You can’t start a fire without a spark
This gun’s for hire
Even if we’re just dancing in the dark

You sit around getting older
There’s a joke here somewhere and it’s on me
I’ll shake this world off my shoulders
Come on, baby, the laugh’s on me

Stay on the streets of this town
And they’ll be carving you up all right
They say you gotta stay hungry
Hey, baby, I’m just about starving tonight

I’m dying for some action
I’m sick of sitting ’round here trying to write this book
I need a love reaction
Come on now, baby, gimme just one look

You can’t start a fire
Sitting ’round crying over a broken heart
This gun’s for hire
Even if we’re just dancing in the dark

You can’t start a fire
Worrying about your little world falling apart
This gun’s for hire
Even if we’re just dancing in the dark
Even if we’re just dancing in the dark
Even if we’re just dancing in the dark
Even if we’re just dancing in the dark
Hey, baby

34. Only Love Can Break Your Heart
Written by: Neil Young
Performed by: Neil Young

As I’ve grown older, I’ve become more of a Neil Young fan. That wasn’t always the case. Even as much as I liked Crosby, Stills, Nash, and Young, I really didn’t like Young all that much. I still can’t say I’m a huge fan, but I really have come to appreciate his music.

“Only Love Can Break Your Heart” is a beautiful song. It may not be as sad as some of the other songs on the list, but I think it still belongs. Give it a listen.

Only Love Can Break Your Heart

When you were young
And on your own
How did it feel to be alone?
I was always thinking of games
That I was playing
Trying to make the best of my time

But only love can break your heart
Try to be sure right from the start
Yes, only love can break your heart
What if your world should fall apart?

I have a friend I’ve never seen
He hides his head inside a dream
Someone should call him and see
If he can come out
Try to lose the down that he’s found

But only love can break your heart
Try to be sure right from the start
Yes, only love can break your heart
What if your world should fall apart?

I have a friend I’ve never seen
He hides his head inside a dream

Yes, only love can break your heart
Yes, only love can break your heart
Yes, only love can break your heart
Yes, only love can break your heart
Yes, only love can break your heart

36. I Will Always Love You
Written by: Dolly Parton
Performed by: Dolly Parton/Whitney Houston

Can we just take a moment to celebrate the awesomeness of Dolly Parton? She’s a national treasure. She has done a lot of great songs, a lot of sad songs, but it was Whitney Houston that really brought this song to life. Watch the two videos below. Dolly’s is good. Whitney’s is out of this world.

The very first stanza of the song tells the story. “If I should stay, I would only get in your way. So I’ll go, but I know I’ll think of you every step pf the way.” They’re breaking up, but she doesn’t want to. She’s doing it for him. #Sad.

I Will Always Love You

If I should stay
I would only be in your way
So I’ll go but I know
I’ll think of you every step of the way

And I will always love you
I will always love you

You
My darling, you
Mmm-mm

Bittersweet memories –
That is all I’m taking with me
So good-bye
Please don’t cry:
We both know I’m not what you, you need

And I… will always love you
I… will always love you
You, ooh

I hope life treats you kind
And I hope you have all you’ve dreamed of
And I’m wishing you joy and happiness
But above all this, I wish you love

And I… will always love you
I will always love you
I will always love you
I will always love you
I will always love you
I, I will always love you
You
Darling, I love you
I’ll always
I’ll always love you

 

37. My Heart Will Go On
Written by: James Horner and Will Cummings
Performed by: Celine Dion

When I think about “My Heart Will Go On,” I think about my daughter. She was just two years old in 1997 when the song came out, and she loved it. I remember one day, sitting at my in-laws’ house, and my daughter wanted to play the song over and over and over. She sang along with Celine Dion, and I was surprised that at just two years old, she was pretty good. Of course, I’m not biased.

“My Heart Will Go On” was from the movie Titanic, which was about a forbidden love affair that ended with Jack (Leonardo DiCaprio’s character) drowning in frigid cold waters after the Titanic–the “unsinkable ship,”–hits an iceberg and sinks. Sad stuff indeed.

My Heart Will Go On

Every night in my dreams
I see you, I feel you
That is how I know you go on

Far across the distance
And spaces between us
You have come to show you go on

Near, far, wherever you are
I believe that the heart does go on
Once more you open the door
And you’re here in my heart
And my heart will go on and on

Love can touch us one time
And last for a lifetime
And never let go ’til we’re gone

Love was when I loved you
One true time I hold to
In my life we’ll always go on

Near, far, wherever you are
I believe that the heart does go on
Once more you open the door
And you’re here in my heart
And my heart will go on and on

You’re here, there’s nothing I fear
And I know that my heart will go on
We’ll stay forever this way
You are safe in my heart
And my heart will go on and on

38. How Can You Mend a Broken Heart
Written by: Barry Gibb & Robin Gibb
Performed by: Bee Gees/Al Green

The Bee Gee are underrated. There, I said it. For people my age, when we were young, the Bee Gees were looked at as a disco group. And we were not fans of disco. But if you look at the Bee Gees entire discography, it’s obvious that they were much more than just a disco group. They were a great band.

Al Green (before he was Rev. Al Green) did a cover of “How Can You Mend a Broken Heart” and made it his own. Man, did he ever make it his own. Take a look at the video to see what I mean.

How Can You Mend a Broken Heart

I can think of younger days when living for my life
Was everything a man could want to do
I could never see tomorrow
But I was never told about the sorrows

And, how can you mend a broken heart?
How can you stop the rain from falling down?
How can you stop the sun from shining?
What makes the world go ’round?
How can you mend this broken man?
How can a loser ever win?
Please help me mend my broken heart and let me live again

I can still feel the breeze that rustles through the trees
And misty memories of days gone by
We could never see tomorrow
No one said a word about the sorrow

And how can you mend a broken heart?
How can you stop the rain from falling down?
How can you stop the sun from shining?
What makes the world go ’round?
And how can you mend this broken man?
How can a loser ever win?
Please help me mend my broken heart and let me live again

39. Someone You Loved
Written by: Lewis Capaldi
Performed by: Lewis Capaldi

“Some You Loved” is sad on a couple of different levels. First, the lyrics tell the story of a guy who used to be in a relationship, still wants to be in the relationship, but isn’t in the relationship anymore. And he’s struggling with that fact. He fell in love, let his guard down, and now he’s dealing with the pain.

But it’s the writer and performer’s life that is even more sad. Lewis Capaldi is a Scottish musician who burst onto the scene with “Someone to Love.” But shortly after realizing his dream of become a successful musician, he was diagnosed with Tourette’s Syndrome and debilitating anxiety. Medicine can help both ailments, but it dulls his faculties, making it difficult to write songs and impossible to perform them the way he wants. Sometimes it’s easier not to realize your dream than it is to realize it and have it ripped away.

Someone You Loved

I’m going under and this time I fear there’s no one to save me
This all or nothing really got a way of driving me crazy

I need somebody to heal
Somebody to know
Somebody to have
Somebody to hold
It’s easy to say
But it’s never the same
I guess I kinda liked the way you numbed all the pain

Now the day bleeds
Into nightfall
And you’re not here
To get me through it all
I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

I’m going under and this time I fear there’s no one to turn to
This all or nothing way of loving got me sleeping without you

Now, I need somebody to know
Somebody to heal
Somebody to have
Just to know how it feels
It’s easy to say
But it’s never the same
I guess I kinda liked the way you helped me escape

Now the day bleeds
Into nightfall
And you’re not here
To get me through it all
I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

And I tend to close my eyes when it hurts sometimes
I fall into your arms
I’ll be safe in your sound til I come back around

For now the day bleeds
Into nightfall
And you’re not here
To get me through it all
I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

But now the day bleeds
Into nightfall
And you’re not here
To get me through it all
I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

40. The Boxer
Written by: Paul Simon
Performed by: Simon & Garfunkel

For most of my life, I have believed that “The Boxer” begins with the lines “I am just a poor boy, though my story’s seldom told. I have squandered my existence for a pocket full of mumbled sunshine promises.” As you can see below, I was wrong. That, in and of itself is sad.

But the lyrics are the story here. The song’s narrator tells about his efforts to overcome loneliness and poverty, then switches to a third-party lament about a boxer who “carries the reminder of every glove that laid him down or cut him till he cried out.” Is the boxer a metaphor for what the narrator is going through? It seems that way to me. Either way, it’s powerful stuff.

The Boxer

I am just a poor boy
Though my story’s seldom told
I have squandered my resistance
For a pocketful of mumbles
Such are promises
All lies and jest
Still, a man hears what he wants to hear
And disregards the rest

When I left my home and my family
I was no more than a boy
In the company of strangers
In the quiet of a railway station
Running scared
Laying low, seeking out the poorer quarters
Where the ragged people go
Looking for the places only they would know

Lie-la-lie…

Asking only workman’s wages
I come looking for a job
But I get no offers
Just a come-on from the whores on Seventh Avenue
I do declare there were times when I was so lonesome
I took some comfort thereLie-la-lie…

Then I’m laying out my winter clothes
And wishing I was gone
Going home
Where the New York City winters aren’t bleeding me
Leading me
Going home

In the clearing stands a boxer
And a fighter by his trade
And he carries the reminders
Of every glove that laid him down
Or cut him ’til he cried out
In his anger and his shame
“I am leaving, I am leaving”
But the fighter still remains

Lie-la-lie…

41. Something in the Way
Written by: Kurt Cobain
Performed by: Nirvana

Truth is, I had never heard “Something in the Way” before someone suggested to me that it should be on my list. I listened to it. Sure enough, it’s sad. I think it’s about a homeless person, but I’m honestly not sure.

That’s it. That’s the whole story.

Something in the Way

Underneath the bridge
Tarp has sprung a leak
And the animals I’ve trapped
Have all become my pets
And I’m living off of grass
And the drippin’s from the ceiling
It’s okay to eat fish
‘Cause they don’t have any feelings

Something in the way, mmm
Something in the way, yeah, mmm
Something in the way, mmm
Something in the way, yeah, mmm
Something in the way, mmm
Something in the way, yeah, mmm

Underneath the bridge
Tarp has sprung a leak
And the animals I’ve trapped
Have all become my pets
And I’m living off of grass
And the drippings from the ceiling
It’s okay to eat fish
Cause they don’t have any feelings

Something in the way, mmm
Something in the way, yeah, mmm
Something in the way, mmm
Something in the way, yeah, mmm
Something in the way, mmm
Something in the way, yeah, mmm
Something in the way, mmm
Something in the way, yeah, mmm

42. Wicked Game
Written by: Chris Isaak
Performed by Chris Isaak/Tenacious D

If you’re around my age, you probably remember this song as the one with the uncomfortably sexy video of an impossibly handsome Chris Isaak chasing a beautiful, topless woman around the beach, the whole time singing about how he doesn’t want to fall in love. He claims the woman is playing a wicked game, drawing him in, letting him dream about her, making him fall in love. He knows the world is going to break his heart, but he can’t help himself. Then the song ends with the words, “Nobody loves no one.” That’s sad, isn’t it?

Chris Isaak does the OG version of this song. His video looks like one of those black and white perfume commercials that makes no sense. I really like the cover done by Tenacious D. Sometime I forget how really talented Jack Black is.

Wicked Game

The world was on fire and no one could save me but you
It’s strange what desire will make foolish people do
I never dreamed that I’d meet somebody like you
And I never dreamed that I’d lose somebody like you

No, I don’t wanna fall in love
(This world is only gonna break your heart)
No, I don’t wanna fall in love
(This world is only gonna break your heart)
With you, with you (With you)
(This world is only gonna break your heart)

What a wicked game we play, to make me feel this way
What a wicked thing to do, to let me dream of you
What a wicked thing to say, you never felt this way
What a wicked thing to do, to make me dream of you

And I don’t wanna fall in love
(This world is only gonna break your heart)
No, I don’t wanna fall in love
(This world is only gonna break your heart)
With you

The world was on fire and no one could save me but you
It’s strange what desire will make foolish people do
I never dreamed that I’d love somebody like you
And I never dreamed that I’d lose somebody like you

No, I don’t wanna fall in love
(This world is only gonna break your heart)
No, I don’t wanna fall in love
(This world is only gonna break your heart)
With you (With you)
(This world is only gonna break your heart)
With you (With you)
(This world is only gonna break your heart)
No, I… (This world is only gonna break your heart)
(This world is only gonna break your heart)

Nobody loves no one

 

43. Unchained Melody
Written by: Alex North & Hy Zaret
Performed by: The Righteous Brothers

This one is a classic. And although it seems like I’ve known this song my entire life (it was first recorded by Todd Duncan in 1955), I never knew why it was called “Unchained Melody.” The answer was uninspiring. It seems that the song was written for the movie Unchained, and because of that, was tentatively titled “Unchained Melody.” I don’t know if the writers didn’t think much of the song or they just got busy, but they never bothered to rename it. It’s a great song and it deserved better.

The song was recorded hundreds of times by singers including George Benson, Neil Diamond, Leo Sayer, and even U2. But there are two versions that stand out. The Righteous Brothers version really put the song on the map, and their version found new life in the movie Ghost. The Elvis Presley cover is like nothing else, putting his soaring vocals on full display. I challenge you to watch the video and not get chills.

Unchained Melody

Oh, my love
My darling
I’ve hungered for your touch
A long, lonely time

And time goes by so slowly
And time can do so much
Are you still mine?

I need your love
I need your love
God speed your love to me

Lonely rivers flow to the sea, to the sea
To the open arms of the sea
Yes, lonely rivers sigh, “Wait for me, wait for me
I’ll be coming home, wait for me”

Oh, my love
My darling
I’ve hungered, hungered for your touch
A long, lonely time

And time goes by so slowly
And time can do so much
Are you still mine?

I need your love
I, I need your love
God speed your love to me

44. Yesterday
Written by: Paul McCartney and John Lennon
Performed by: The Beatles

“Yesterday, all my troubles seemed so far away. Now it look as though they’re here to stay. I believe in yesterday.” You don’t need much more than that to know the story the singer s telling.

Writing the song was not nearly as sad as the song itself. According to Paul McCartney, the song came to him one night in a dream. But the lyrics were unfinished. Originally, the song started with the lines “Scrambled eggs/Oh my baby how I Iove your legs/Not as much as I love scrambled eggs.” McCartney knew the scrambled eggs lyrics weren’t going to stay, but he kept them as a placeholder until he found something more suitable. I’ll never be able to eat scrambled eggs again without thinking about this song.

Yesterday

Yesterday all my troubles seemed so far away.
Now it looks as though they’re here to stay.
Oh, I believe in yesterday.

Suddenly, I’m not half the man I used to be.
There’s a shadow hanging over me.
Oh, yesterday came suddenly.

Why she had to go?
I don’t know, she wouldn’t say.
I said something wrong.
Now I long for yesterday.

Yesterday love was such an easy game to play.
Now I need a place to hide away.
Oh, I believe in yesterday.

Why she had to go?
I don’t know, she wouldn’t say.
I said something wrong.
Now I long for yesterday.

Yesterday love was such an easy game to play.
Now I need a place to hide away.
Oh, I believe in yesterday.

Mm mm mm mm mm mm mm.

45. I Will Remember You
Written by: Sarah McLachlan, Seamus Egan, and Dave Merenda
Performed by: Sarah McLachlan

Is it just me, or can you not hear a Sarah McLachlan song without thinking of those ultra-sad ASPCA commercials that show scared and hungry dogs living in horrible conditions. Every time I see one, I want to yell at the cameraman, “Put the camera down and help those poor dogs.” But no, the cameraman can’t help the dogs. Only your donation of just $19/month can do that.

Anyway, this is a sad song. Now, all I can think about are those poor dogs.

I Will Remember You

I will remember you
Will you remember me?
Don’t let your life pass you by
Weep not for the memories

Remember the good times that we had?
I let them slip away from us when things got bad
How clearly I first saw you smilin’ in the sun
Wanna feel your warmth upon me, I wanna be the one

I will remember you
Will you remember me?
Don’t let your life pass you by
Weep not for the memories

I’m so tired but I can’t sleep
Standin’ on the edge of something much too deep
It’s funny how we feel so much but we cannot say a word
We are screaming inside, but we can’t be heard

But I will remember you
Will you remember me?
Don’t let your life pass you by
Weep not for the memories

I’m so afraid to love you, but more afraid to lose
Clinging to a past that doesn’t let me choose
Once there was a darkness, deep and endless night
You gave me everything you had, oh you gave me light

And I will remember you
Will you remember me?
Don’t let your life pass you by
Weep not for the memories

And I will remember you
Will you remember me?
Don’t let your life pass you by
Weep not for the memories
Weep not for the memories

46. Wildfire
Written by: Michael Martin Murphey and Larry Cansler
Performed by: Michael Martin Murphey

I first met Michael Martin Murphey in 2003. He had recently moved to my area of Wisconsin from his home state of Texas after marrying a woman from our neighboring town. I was the president of our local Rotary Club at the time and Michael was interested in joining.

I think I may have been the only member of our Rotary Club who knew who Michael was. At that first meeting he introduced himself and  said he was a musician. “What kind of music do you play” someone asked him. He asked, “You heard of country and western?” Everyone said they had. “And you know what country music is?” Again, everyone say they did. “Well, I do the western kind.” I’ve had the great good fortune to hear Michael perform “Wildfire” three or four times since then, both solo and with his band.

“Wildfire” is a terrific song that tells a sad story about a horse named Wildfire that gets loose in a blizzard and runs off.  Wildfire’s owner chases after the horse, but they both die in the heavy snow. The song goes on, switching to the prospective of a farmer who knows the story of Wildfire and his owner, and fears–or maybe wants–them to come take him away from the sodbusting life.

Wildfire

She comes down from yellow mountain
On a dark, flat land she rides
On a pony she named wildfire
With a whirlwind by her side
On a cold Nebraska night

Oh, they say she died one winter
When there came a killing frost
And the pony she named wildfire
Busted down his stall
In a blizzard, she was lost

She ran calling wildfire
Calling wildfire
Calling wildfire

So by the dark of the moon, I planted
But there came an early snow
Been a hoot-owl howling outside my window now
‘Bout six nights in a row
She’s coming for me, I know
And on wildfire we’re both gonna go

We’ll be ridin’ wildfire
Ridin’ wildfire
Ridin’ wildfire

On wildfire we’re gonna ride
Gonna leave sodbustin’ behind
Get the hard times right on out of our minds
Riding wildfire

47. Stay With Me
Written by: Sam Smith, Kames Napier, William Phillips, Tom Petty, Jeff Lynne
Performed by: Sam Smith

“Stay With Me” is Sam Smith’s most popular song. But it’s birth was a controversial one. After it was released, Tom Petty’s estate contacted Smith claiming that “Stay With Me” sounded suspiciously like Petty’s single “I Won’t Back Down,” which had been written by Petty and Lynne. Turns out they were right. Petty and Lynne got co-writing credit and 12.5% of the proceeds from the song.

Stay With Me

Guess it’s true, I’m not good at a one-night stand
But I still need love ’cause I’m just a man
These nights never seem to go to plan
I don’t want you to leave, will you hold my hand?

Oh, won’t you stay with me?
‘Cause you’re all I need
This ain’t love, it’s clear to see
But, darling, stay with me

Why am I so emotional?
No, it’s not a good look, gain some self-control
And deep down I know this never works
But you can lay with me so it doesn’t hurt

Oh, won’t you stay with me?
‘Cause you’re all I need
This ain’t love, it’s clear to see
But, darling, stay with me

Oh, won’t you stay with me?
‘Cause you’re all I need
This ain’t love, it’s clear to see
But, darling, stay with me

Oh, won’t you stay with me?
‘Cause you’re all I need
This ain’t love, it’s clear to see
But, darling, stay with me

48. The Living Years
Written by: B.A. Robertson and Mike Rutherford
Performed by: Mike + The Mechanics

The song was inspired by the fact that both Robertson and Rutherford lost their fathers when they were young. The similarity got the two talking, and they realized how the previous generation had wanted to follow in their fathers’ footstep, but then things changed and young men suddenly didn’t want to be like their fathers. For the songwriters, the change wasn’t brought on by anything the fathers had done. It was just a cultural shift. But the change negatively impacted relationships between fathers and sons.

I especially like the lyric “I wasn’t there that morning/When my Father passed away/I didn’t get to tell him/All the things I had to say.” Every time I hear it, I think of my own dad.

The Living Years

Every generation
Blames the one before
And all of their frustrations
Come beating on your door

I know that I’m a prisoner
To all my Father held so dear
I know that I’m a hostage
To all his hopes and fears
I just wish I could have told him in the living years

Crumpled bits of paper
Filled with imperfect thought
Stilted conversations
I’m afraid that’s all we’ve got

You say you just don’t see it
He says it’s perfect sense
You just can’t get agreement
In this present tense
We all talk a different language
Talking in defense

Say it loud, say it clear
You can listen as well as you hear
It’s too late when we die
To admit we don’t see eye to eye

So we open up a quarrel
Between the present and the past
We only sacrifice the future
It’s the bitterness that lasts

So don’t yield to the fortunes
You sometimes see as fate
It may have a new perspective
On a different date
And if you don’t give up, and don’t give in
You may just be O.K.

Say it loud, say it clear
You can listen as well as you hear
It’s too late when we die
To admit we don’t see eye to eye

I wasn’t there that morning
When my Father passed away
I didn’t get to tell him
All the things I had to say

I think I caught his spirit
Later that same year
I’m sure I heard his echo
In my baby’s new born tears
I just wish I could have told him in the living years

Say it loud, say it clear
You can listen as well as you hear
It’s too late when we die
To admit we don’t see eye to eye

49. From His Window
Written by: John Smith
Performed by: John Smith

John Smith is a friend of mine from Trempealeau, WI. He’s a terrific singer-songwriter who also leads trips to Ireland (something I want to go on one of these days). John’s song “From His Window” is autobiographical, about his father who had Alzheimer’s. John’s dad was in a nursing home, and although he didn’t always remember John, he did enjoy when John visited. In the song, John had spent some time with his dad, but had to leave. John went out to his car, and as he was pulling out of the parking lot, he looked back, and his dad was in his window, waving, watching John drive away. It’s a heartbreaking song.

John tells the story about playing “From His Window” in a pub in Ireland several years ago. As often happened, tears were flowing by the end of the song. The audience in the pub applauded, and in the quiet after the applause died down, a lone voice from the back of the room called out to John in an Irish brogue, “That’s a good one, John. But can you play us a sad song?”

I would encourage you to watch the video for John’s song. But let me warn you, you might want to have some tissues handy. I think you’ll need them

From His Window

He stands by the window
He watches cars go by
He waves at everybody
He’s just a friendly guy

He doesn’t know what day it is
He doesn’t talk much anymore
Sometimes he cries when he means to laugh
Doctors say he can’t tell that

And I come to visit
I take him out on drives
He wants to go home with me
Evertime

But the nurses come to take him
Back to his room that’s waiting
And I fight to keep my tears inside
From his window, he waves goodbye

Where have the years all gone to
It seems like only yesterday
We used to dance upon his shoes
Back on Sunday afternoons

He was a mountain standing tall
Doing his best to raise us all
We always had enough to eat
He worked two jobs to make ends meet

But now it seems he can’t remember that
And it’s hard for the rest of us to understand
But when I come to visit, he knows my name and he says it
And I fight to keep my tears inside

From his window
He waves goodbye

But when I come to visit, he knows my name and he says it
And it makes me glad I made the drive
From his window
He waves goodbye

From his window
He waves goodbye

50. Danny Boy
Written by: Frederic Weatherly
Performed by: Various

There are several different stories about how “Danny Boy” came into existence. What is known is that the lyrics were written in 1910 by British lawyer and lyricist (This two job descriptions rarely goes together) Frederic Weatherly. The music for “Danny Boy comes from “Londonderry Air,” but it’s unknown exactly how the lyrics and music came together.

Although it’s hard to know exactly the meaning behind the lyrics, it is believed that they are a message from a family to a son going off to war. Considering that the song was written in 1910, the war was likely World War I.

A million different artists have recorded “Danny Boy,” and it was a little hard choosing exactly with version to include here. In the end, I decided to share a traditional version of the song by Jim McCann and The Dubliners, as well as a wonderful, over-the-top version by Tom Jones.

Danny Boy

Oh, Danny boy, the pipes, the pipes are calling
From glen to glen, and down the mountain side.
The summer’s gone, and all the roses falling,
It’s you, it’s you must go and I must bide.
But come ye back when summer’s in the meadow,
Or when the valley’s hushed and white with snow,
It’s I’ll be there in sunshine or in shadow,—
Oh, Danny boy, Oh Danny boy, I love you so!

But when ye come, and all the flowers are dying,
If I am dead, as dead I well may be,
Ye’ll come and find the place where I am lying,
And kneel and say an Avé there for me.
And I shall hear, though soft you tread above me,
And all my grave will warmer, sweeter be,
For you will bend and tell me that you love me,
And I shall sleep in peace until you come to me!

 

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