Songs that Make You Sad: Are You Ready To Be Heartbroken

Stunning. She is just amazing. I saw her and Dave earlier this year in OKC from the front row center with elbows propped up on the stage. Amazing show. I just love those two.

 

There are a bunch by Randy Newman
Marie
Real Emotional Girl
I Want You To Hurt Like I Do
Every Time It Rains
When She Loved Me
to name but five. Tears aren't necessarily the appropriate response sometimes but I can't help it. They get to me.

 

There is a great version done for TV in the UK with Steve and Emmylou duetting on the song. It is devastating. Try and track it down.

 

Neutral Milk Hotel - Two Headed Boy, Pt 2, just emotionally heart wrenching

 

I have many. Some are specific to a moment, a woman, others are more general. Some are sad and beautiful and I just wallow in them and enjoy it. It's a luxury really. Here's one that I really love - great guitar work, great late night FM radio song. That's where I first heard it, late at night in the late 70's on commercial free overnight album rock...

 

Perhaps not heartbroken, but Fogelberg’s Auld Lang Syne always has rung a sad chord.....high school crush who birthed my older daughter.
“ If it were not for poorly trod ground that which isn’t would seem too familiar”

 

I have to give you kudos for the Mott avatar!

 

Maybe it's just me, but there's something about "Living it Up" by Rickie Lee Jones (Pirates) that makes me bluer than blue. It's not so much the lyrics, per se. It's the music. RLJ also sings "yeah, we're living it up" in a way that I'd imagine a woman who's led a really tough life and is desperately trying to convince herself that it's not that bad might sing it. Not saying the song is autobiographical, just the way that character in the song makes me feel.

 

I second your kudos on ' Mott '...

 

“Puff the Magic Dragon”

 

There's not much that's sadder than a stillborn child -

Rejoice!, November Snow:

 

“Walk Away Renee” - The Four Tops (I prefer the Four Tops version)

 

Sad songs for me as main preferences...

1.Dylan / Ballad Of Hollis Brown (1963)...I live in Little Siberia AKA Red River Valley of Minnesota & every time I play that song I can hear sub-zero Alberta Clipper winds howling regardless of the season, a song that once you hear it you never forget it

2.Van Morrison / Madame George (1968)...Astral Weeks was the record that spent more time on my TT during 1968 than anything else & the pain that Van evokes on "Cypress Avenue" & "Madame George" remains almost unbearable at times

3.Irma Thomas / I Wish Someone Would Care (1961)...possibly the saddest song ever written

4.Ray Charles / Drown In My Own Tears (1960)....the ultimate in defeat

5.Country Joe McDonald / Jean Desprez (1971)...Joe took the poems of WW1 veteran Robert Service & put them to music & the horrendous execution of young French freedom fighter Jean Desprez at the hands of a Prussian commander is heartbreaking, no matter how many times I play it...

The 1st time I heard this on my TT during 1971 I was left speechless by the power & commitment my favorite 1960s artist had brought to every performance on this forgotten masterpiece of a record...

Not for the faint of heart

6.Steely Dan / Charlie Freak (1974)...Fagen & Becker at their saddest

7.Smokey & Miracles / The Love I Saw In You Was Just A Mirage (1966)...a song so gentle it made everything else surrounding it on the radio sound obscene, Smokey at his heartbroken best

8.Hank Williams / I'm So Lonesome I Could Cry (1953)...along with Irma Thomas this is probably the greatest performance of loneliness ever recorded

9.KoKo Taylor / Insane Asylum (196)...written by Willie Dixon who also produced & lends his vocals as her lover, a tale so frightening & heartbreaking no one would dare attempt to cover it...

One of the most powerful performances ever recorded in any genre

10.Marianne Faithful / The Ballad of Lucy Jordan (1979)...her cover of this Dr.Hook classic is definitive & reminds me of what Marianne had been dealing with lo all those years prior

Honorable mention : Elton John / Candle In The Wind (1973)...Elton's performance of his farewell to Marilyn elevates this to unbelievable heights

 

Here's a feel good number...

 

So many of Townes' tunes just rip your heart out. When listening to him I often find myself thinking what it must have been to live his life. I've read 2 bios, listened to everything he's recorded and seen the movie. But still I wonder.

 

Can't Cry Hard Enough... the Victoria Williams version. The sole song I chose to play at my mom's funeral... in spite of the fact it was suggested I not play any music.

And while I'm on the theme of crying I'll add the Hank Williams eternal 1941 classic... I'm So Lonesome I Could Cry.

 

“The Bitterest Pill” - The Jam

 

Surprised “Cats in the Cradle,” by Harry Chaplin hasn’t been mentioned yet

 

All My Friends from Greg Allman's Laid Back recording. When Greg sing, "all my friends, came to see me this year". I know it wasn't what Cowboy Boyer said the song was about but I find it impossible to hear anything other then Greg singing about the aftermath of brother Duane's death. The lyric and the intimate way Greg puts it across always gets to me.

 

Pineola yes! As well as a number of other Lucinda tunes.

 

Can't hear this without thinking of the scene in ' Meet the Parents " where Ben Stiller is telling DeNiro about how the song is about marijuana. ..

 

Samthesham , my man , your list and commentary are absolutely spot on in every regard. You nailed it on each song you mentioned and have defined this thread by doing so.
Great list and even greater comments.
Cheers , mate !

 

Yeah , this one can really get to you sometimes...

 

Oh ! Forgot to mention that Kathi McDonald did a very good cover of 'Insane Asylum' on her debut album with -wait for it- Sly Stone as the lover.