When you are far away
And I am blue
What'll I do?
- Judy Garland
And I am blue
What'll I do?
- Judy Garland
I totally stole this idea from Jera, but I love making up fun lists -- hey, A.D.D. moment -- anyone remember "The Book of Lists" ?? I used to check them out of the library as a kid. They were a lot of fun. ANYWAY...
I think really rip-your-heart-out-of-your-chest songs are my favorite. I love good lyrics and depressing ballads. Go figure. So, I'm including my own Saddest Songs of all Time list. Before I go look at the website that Jera suggested with their own saddest songs of all time, and get myself all influenced, I'm going to list several of my own first, and invite you to do the same!
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POP-n-ROCK-n-R&B-n-JAZZ CATEGORY
Here's That Rainy Day
by Ella Fitzgerald

Ella and Billie sang great sad songs, but this is one of my favorites. I saw a clip of Bette Midler, cheek to cheek with Johnny Carson, singing a line from this song, pretty sweet. The song itself is short and sweet, talking of how though cautioned regarding the dangers of love, we always end up stunned in its bitter aftermath.
Maybe I should have saved
Those leftover dreams
Funny, here's that rainy day
Here's that rainy day they told me about
And I laughed at the thought
That it might turn out this way
Those leftover dreams
Funny, here's that rainy day
Here's that rainy day they told me about
And I laughed at the thought
That it might turn out this way
Why Should I Cry For You?
by Sting
- This is one of my favorite songs of all time about a man on a ship somewhere in the Arctic, late at night, accepting not only the failure of his relationship, but a lifetime of solitude "hauling on frozen ropes for all my days remaining." And at the risk of sounding weird, I think there's something very male about this song - its stoic resignation. I know there are instances when someone loves you with all their heart, but it's not the way you are expecting/wanting, and that can be hard for both to accept.
Why should I cry for you?
Why would you want me to?
What would it mean to say,
I loved you in my fashion
Why would you want me to?
What would it mean to say,
I loved you in my fashion
Tonight

by Elton John (also beautifully sung by George Michael)
- A 7-minute song with a haunting 3-minute piano intro (it's what made me really want to learn how to play the piano!), this song of lost hope tells the story of a man who has been in a relationship of non-stop fighting for so long, and just wants a little bit of peace, and maybe, a small reminder of what it once was before everything was a battle.
Tonight, does it have to be the old thing?
Tonight, Oh, it's late, too late
To chase the rainbow that you're after
I'd like to find a compromise
And place it in your hands
My eyes are blind, my ears can't hear,
And I cannot find the time
Tonight, Oh, it's late, too late
To chase the rainbow that you're after
I'd like to find a compromise
And place it in your hands
My eyes are blind, my ears can't hear,
And I cannot find the time
Wonderful World
by James Morrison
- Yeah, don't be fooled by the title (or the somewhat boppy melody), it's the song about knowing you should recognize the beauty around you, but no matter how you try, life sucks and you just can't at this time. Who hasn't felt like that before?
And I know it's a wonderful world, but I can't feel it right now
Well, I thought that I was doing well, but I just want to cry now
Well, I thought that I was doing well, but I just want to cry now
What If?
by Kate Winslet
- Ahhh regret. What if? What if! Kate Winslet - yes, she can sing! - from a cartoon version of The Christmas Carol, no less - sings about a heartbroken woman and that nagging question!
What if I had never let you go
Would you be the man I used to know
If I'd stayed, if you'd tried
If we could only turn back time
But I guess, we'll never know
Would you be the man I used to know
If I'd stayed, if you'd tried
If we could only turn back time
But I guess, we'll never know
Lately
by Stevie Wonder (great remake by K-CI & Jo-Jo too)
- The heartbreaking song of a man who sees the signs of his wife's infidelity, but is hoping, desperately hoping, that he is wrong.
Far more frequently you're wearing perfume
With you say, "No special place to go"
But when I ask will you be coming back soon
You don't know, never know
I'm a man of many wishes
Hope my premonition misses
But what I really feel
My eyes won't let me hide
Cause they always start to cry
With you say, "No special place to go"
But when I ask will you be coming back soon
You don't know, never know
I'm a man of many wishes
Hope my premonition misses
But what I really feel
My eyes won't let me hide
Cause they always start to cry
Philadelphia
by Bruce Springsteen
- No one talks about this very 90's movie/song anymore, but it's
personal for me. It was around the time of my grandfather's death, a man who was "terminally ill" for 20 years with heart disease, but who truly deteriorated during the last two years. I choke up every time at the line "...and my clothes don't fit me no more" since I remember my grandfather telling me that very same thing at that time, with some sadness. The following lines make me think of his final night (he died in his sleep): Night is falling, I'm lying awake
I can feel myself fading away...
I can feel myself fading away...
Broken Vow
by Josh Groban
- Sure, he's a hokie dude, but he can really blow your socks off with the emotion in his voice. Nothing says sadness like total betrayal.
Tell me his name I want to know
The way he looks and where you go
I need to see his face, I need to understand
How you and I came to an end
--------------------------The way he looks and where you go
I need to see his face, I need to understand
How you and I came to an end
BROADWAY CATEGORY
Broadway is good for the spotlight on the utter crappiness of life number, usually sung by a lone female about halfway through the show. I've picked two:
I'm Not That Girl
by Idina Menzel in "Wicked"
- H
ow shitty is life when you are deep in love, but know you are competing with the pretty, popular, perky girl and that you disappear when she is around? This song takes the low self-esteem thing even farther where the singer (who just happens to be the pre-Wicked Witch of the East), doubts she even has the right to dream since she's not "that girl." Don't wish, don't start
Wishing only wounds the heart
I wasn't born for the rose and the pearl
He could be that boy
I'm not that girl"
Wishing only wounds the heart
I wasn't born for the rose and the pearl
He could be that boy
I'm not that girl"
On My Own
sung by 'Eponine' in "Les Miserables"
- Poor Eponine's haunting words float around her as she walks along the Seine all night, in the empty, rainy streets of Paris (are the streets of Paris EVER empty?). She pines away for the man who loves another girl and barely notices her (see a theme here?). How does she cope? By creating an intricate fantasy land where she turns him into an imaginary friend who loves only her until dawn, of course!sung by 'Eponine' in "Les Miserables"
I love him, but when the night is over
He is gone, the river's just a river
Without him, the world around me changes
The trees are bare, and everywhere
The streets are full of strangers
------------------------------------He is gone, the river's just a river
Without him, the world around me changes
The trees are bare, and everywhere
The streets are full of strangers
COUNTRY CATEGORY
This category could go on forever (as you'll see by Beau's picks), but I just picked two, though you could easily add Johnny Cash's version of NIN's Hurt if you want to feel extra crappy.
Stupid Boy
by Keith Urban
- Oh, how we all wish our jerkoff ex's would just mourn, regret, and pine away after we finally got smart and dumped their sorry ass. Usually, they don't, but once in awhile they do, and this song helps satisfy that selfish feeling.
She laid her heart and soul right in your hands
And you stole her every dream and you crushed her plans
She never even knew she had a choice
And that's what happens when
The only voice she hears is telling her she can't
You stupid boy.
And you stole her every dream and you crushed her plans
She never even knew she had a choice
And that's what happens when
The only voice she hears is telling her she can't
You stupid boy.
The Silver Dagger
by Dolly Parton (remake by Solas)
- Dolly Parton doesn't get enough credit for her work, since the focus is on other things, but some of her stuff is great. This early song, which to me, is a very
Celtic-like ballad (hence, the great band Solas did their own version!), tells the story of a young girl whispering to her lover outside her window, refusing him, because her mother has convinced her that men are all scumbags who love you and leave you. I don't know what's the bigger tragedy, that the girl is choosing a lifetime of loneliness, or that her mother (because of her father's cheating ways) has convinced her daughter to do so. Go court another tender maiden
In hopes that she may be your bride
For I've been warned, so I've decided
I'll sleep alone all of my life
In hopes that she may be your bride
For I've been warned, so I've decided
I'll sleep alone all of my life
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FOREIGN CATEGORY
I had two for this, but this list is getting REALLY long, so I'll just put one:
Ne Me Quitte Pas

by Jacques Brel (remake by Sting)
"Don't Leave Me" is the translation. The entire song, which is very poetic, is basically a man begging a woman not leave him and how his life will just be utter crap if she does. The last lines are both heart-wrenching and strangely humorous. Maybe some of my Canadian friends can tell me if I got it wrong:
Ne me quitte pas (Don't leave me)
Je ne vais plus pleurer (I'm not going to cry anymore)
Je ne vais plus parler (I'm not going to talk anymore)
Je me cacherai la (I will hide myself over there)
A te regarder danser et sourire (To watch you dancing and smiling)
Et a t'ecouter chanter et puis rire (And to listen to you singing and then laughing)
Laisse-moi devenir (Leave me here to become)
L'ombre de ton ombre (The shadow of your shadow)
L'ombre de ta main (The shadow of your hand)
L'ombre de ton chien (The shadow of your dog) !?!?!
Ne me quitte pas... (Don't leave me)
-------------------------Je ne vais plus pleurer (I'm not going to cry anymore)
Je ne vais plus parler (I'm not going to talk anymore)
Je me cacherai la (I will hide myself over there)
A te regarder danser et sourire (To watch you dancing and smiling)
Et a t'ecouter chanter et puis rire (And to listen to you singing and then laughing)
Laisse-moi devenir (Leave me here to become)
L'ombre de ton ombre (The shadow of your shadow)
L'ombre de ta main (The shadow of your hand)
L'ombre de ton chien (The shadow of your dog) !?!?!
Ne me quitte pas... (Don't leave me)
BEAU VOTES
("Geez, J., now you got me all sad thinking about this!")
I'm not a huge country music fan, though there's some stuff I like. Beau is, though thankfully he likes rock too, but all his choices are the 'tear in my beer' country ballads. Sadly, he couldn't come up with all the titles, so if anyone could help out, I'll change it...

Green Green Grass of Home
by Merle Haggard
- Song about a guy on death row
You Never Even Call Me By My Name
by David Alan Coe
- Which features a guy getting out of prison, waiting for his mom to pick him up, but then she gets killed on the way there. (Another prison song. Beau's pattern is giving me a creepy feeling...)
The Night the Lights Went Out in Georgia
by whomever (10,000 remakes)
- Beau: "They're married. She's running around. He dies. She dies. It's sad."
What else needs to be said?
The song about 9-11 by Alan Jackson
He Stopped Loving Her Today
by George Jones
- This one even kills me.
Kept some letters by his bed
Dated 1962
He had underlined in red
Every single "I love you"
Dated 1962
He had underlined in red
Every single "I love you"

4 comments:
Tracy Chapman - "Baby Can I Hold You"
Was my breakup song :(
Oh, I love that song. My favorite song from her (which goes on my favorites of all time list) is "The Promise."
"You Never Even Call Me By My Name" is the David Allan Coe song.
Oooh thanks!
I keep thinking of more songs, of course, like Peter Gabriel/Kate Bush's "Don't Give Up," which is pure beauty.
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