# What are the saddest songs you know? **URL:** \ **Category:** Cafe Society\ **Created:** [April 28, 2002, 12:09am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024 "2002-04-28T00:09:05Z")\ **Posts on this page:** 20\ **Page:** 7
**Author:** ![chief](https://avatars.discourse-cdn.com/v4/letter/c/df788c/32.png) [@chief](https://boards.straightdope.com/u/chief)\ **Post date:** [May 1, 2002, 5:31am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/122 "2002-05-01T05:31:50Z")
Black Crowes - Cursed Diamond, Descending Jeff Buckley - Last Goodbye Wilco - Misunderstood Ben Harper - Walk away, Another Lonely day, Alone, the drugs don’t work (cover) ---
**Author:** ![Happy\_Lendervedder](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/happy_lendervedder/32/8488_2.png) [@Happy\_Lendervedder](https://boards.straightdope.com/u/Happy_Lendervedder)\ **Post date:** [May 1, 2002, 6:17am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/123 "2002-05-01T06:17:45Z")
> [@](#): > > \*Originally posted by MachV \* > \*\ ***Wonderful** by **Everclear**. > > This came out while I was in the middle of a divorce. Although my wife and I were pretty much in agreement on most issues & there was very little drama, our two children were having their world pulled out from under them. This song was (and still is) a very painful reminder of that. \*\* As the 27-year-old child of a divorce that took place 22 years ago, this song brings tears to my eyes to this day. What’s-his-name hit the nail on the head when he wrote this song. stv ---
**Author:** ![Sam\_Stone](https://avatars.discourse-cdn.com/v4/letter/s/ecccb3/32.png) [@Sam\_Stone](https://boards.straightdope.com/u/Sam_Stone)\ **Post date:** [May 1, 2002, 6:52am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/124 "2002-05-01T06:52:54Z")
**Janis Joplin:** Me and Bobby McGee. ---
**Author:** ![ElwoodCuse](https://avatars.discourse-cdn.com/v4/letter/e/edb3f5/32.png) [@ElwoodCuse](https://boards.straightdope.com/u/ElwoodCuse)\ **Post date:** [May 1, 2002, 6:56am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/125 "2002-05-01T06:56:46Z")
I don’t think of Nightswimming as sad. Nightswimming makes me think of good times spent with friends. The first song that ever really got to me was “The Only One” by Huey Lewis. It’s about this guy who gets hit by a car. I would also like to nominate “Evaporated” by Ben Folds Five. Here’s the best line: “I poured my heart out…it evaporated.” ---
**Author:** ![BalmainBoy](https://avatars.discourse-cdn.com/v4/letter/b/6a8cbe/32.png) [@BalmainBoy](https://boards.straightdope.com/u/BalmainBoy)\ **Post date:** [May 1, 2002, 7:44am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/126 "2002-05-01T07:44:57Z")
Think of the ending to **Ol’ Man River** : I gits weary and sick of tryin’; I’m tired of livin’ and scared of dyin’ And Ol’ man river, he just keeps rollin’ along The utter hopelessness of it. So very sad. ---
**Author:** ![gonzoron](https://avatars.discourse-cdn.com/v4/letter/g/a6a055/32.png) [@gonzoron](https://boards.straightdope.com/u/gonzoron)\ **Post date:** [May 1, 2002, 3:34pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/127 "2002-05-01T15:34:02Z")
surprised not to see more tori amos here. my votes are for her: “Northern Lad” and “1000 Oceans” (Especially at time like now when my fiancee, who hooked me on Tori, is an ocean away) ---
**Author:** ![Labdad](https://avatars.discourse-cdn.com/v4/letter/l/439d5e/32.png) [@Labdad](https://boards.straightdope.com/u/Labdad)\ **Post date:** [May 1, 2002, 3:50pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/128 "2002-05-01T15:50:06Z")
Both of Steve Earle’s death penalty songs - “Billy Austin” and “Ellis Unit One” are very sad. They’re very good, but very sad. ---
**Author:** ![a35362](https://avatars.discourse-cdn.com/v4/letter/a/3da27b/32.png) [@a35362](https://boards.straightdope.com/u/a35362)\ **Post date:** [May 1, 2002, 4:04pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/129 "2002-05-01T16:04:28Z")
“Neither One of Us (Wants To Be the First to Say Good-bye)” by Gladys Knight and the Pips is a heartbreaking “the relationship is over and I don’t want to admit it and I don’t want to hurt you, either” song. Comedian Richard Jeni used to tell a story about using “The Wreck of the _Edmund Fitzgerald_” to clear his house when a party was over. The lyrics are so depressing that people would find excuses to leave. 😃 ---
**Author:** ![smoke](https://avatars.discourse-cdn.com/v4/letter/s/c5a1d2/32.png) [@smoke](https://boards.straightdope.com/u/smoke)\ **Post date:** [May 1, 2002, 5:48pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/130 "2002-05-01T17:48:32Z")
Two for me: (forgive me if these have already been nominated) ``` God, John Lennon That's the Way It Should Be, Led Zeppelin ``` Both choke me up every time. -j ---
**Author:** ![Rysdad](https://avatars.discourse-cdn.com/v4/letter/r/7cd45c/32.png) [@Rysdad](https://boards.straightdope.com/u/Rysdad)\ **Post date:** [May 1, 2002, 6:12pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/131 "2002-05-01T18:12:08Z")
> [@](#): > > \*Originally posted by Baker \* > \*\ ***Rysdad** , I guess I never thought of _If You Get There Before I Do_ as a sad song. After all, although the old man misses his wife he _knows_ he will see her again. Sure, I leak a few tears at the song, but that’s because I wish that I could have had a love like theirs. \*\* Well, the old man is still sad about it. The lines preceding my previously quoted verse are: _I read those words just hours before my Grandma passed away, In the doorway of a church where me and Grandpa stopped to pray. I know I’d never seen him cry in all my fifteen years; But as he said these words to her, his eyes filled up with tears._ _sniff_ ---
**Author:** ![Ogre](https://avatars.discourse-cdn.com/v4/letter/o/ecb155/32.png) [@Ogre](https://boards.straightdope.com/u/Ogre)\ **Post date:** [May 1, 2002, 8:52pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/132 "2002-05-01T20:52:33Z")
Two quick ones: A late recording of Hank Williams doing “I Can’t Escape From You.” It was done a few months before he drugged himself to death, and it’s just him and an acoustic guitar. You can hear the terrible sadness and weariness in his voice, and at one point his voice sort of catches in the middle of the chorus, and you can tell his heart was broken. Little Rain (For Clyde) - Tom Waits _She was fifteen years old, and she’d never seen the ocean. She climbed into a van with a vagabond And the last thing she said was, “I love you, mom.” And a little rain never hurt no one._ ---
**Author:** ![katey](https://avatars.discourse-cdn.com/v4/letter/k/a587f6/32.png) [@katey](https://boards.straightdope.com/u/katey)\ **Post date:** [May 1, 2002, 11:28pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/133 "2002-05-01T23:28:34Z")
Two artists already named but I don’t think these songs were mentioned yet: “Fake Plastic Trees” by Radiohead “Lover You Should Have Come Over” by Jeff Buckley And “Sadly Beautiful” by the Replacements ---
**Author:** ![Ogre](https://avatars.discourse-cdn.com/v4/letter/o/ecb155/32.png) [@Ogre](https://boards.straightdope.com/u/Ogre)\ **Post date:** [May 2, 2002, 2:02am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/134 "2002-05-02T02:02:46Z")
Oo oo ooh, katey. You reminded me… “Satisfied Mind,” by Jeff Buckley (yes yes, I know it was originally by Porter Wagonner, so all you musicologists jest calm down.) The lyrics are just so terribly appropriate, since he died so young. It was, in fact, played at his funeral. Plus I’ve never heard his voice more glorious than on that song. ---
**Author:** ![The\_Red\_Menace](https://avatars.discourse-cdn.com/v4/letter/t/82dd89/32.png) [@The\_Red\_Menace](https://boards.straightdope.com/u/The_Red_Menace)\ **Post date:** [May 2, 2002, 2:45am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/135 "2002-05-02T02:45:28Z")
Miles Davis **“Blue In Green”** - The piano at the end of the song is truly haunting. The rest of the album that this tune is on, _Kind of Blue_, is a fantastic downer. I would like to nominate another Jeff Buckley cover as well, this time a Leonard Cohen original: **"Hallelujah"** _well, maybe there’s a god above but all i’ve ever learned from love was how to shoot somebody who outdrew you it’s not a cry that you hear at night it’s not somebody who’s seen the light it’s a cold and it’s a broken hallelujah_ To hear Buckley sing it takes my breath away every time. ---
**Author:** ![Clark\_K](https://avatars.discourse-cdn.com/v4/letter/c/c77e96/32.png) [@Clark\_K](https://boards.straightdope.com/u/Clark_K)\ **Post date:** [May 2, 2002, 3:32am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/136 "2002-05-02T03:32:10Z")
Here area a few of mine: Trisha Yearwood’s “Like We Never Had a Broken Heart” – two people making love just because they have no one else (co-written by Garth Brooks, FYI). It’s the “don’t be afraid to close your eyes” line that gets me. Let’s make love tonight… Like we never had a broken heart… Don’t be afraid to close your eyes… Pretend I’m someone that you love… And I won’t have to tell you lies… ‘Cause it’s not you I’m thinkin’ of… Townes Van Zandt’s “Tecumseh Valley” (especially as performed by Nanci Griffith and Arlo Guthrie). It tells the story of a miner’s daughter who was sent to town for the winter. She saved enough to get back home when spring replaced the winter but her dreams were denied her pa had died the word come down from Spencer So she turned to whorin’ out on the streets with all the lust inside her and it was many a man returned again to lay himself beside her They found her down beneath the stairs that led to Gypsy Sally’s in her hand when she died was a note that cried fare thee well… Tecumseh valley Allison Moorer’s album “The Hardest Part” has a hidden track called “Cold, Cold Earth.” It’s sad by itself, but it’s heartbreaking when you realize she’s singing about the murder-suicide of her parents: A slave to the bottle He’d driven his family to leave A wife and two daughters He treated so terribly He went into the city To try to make amends Asked his love for pity But she would not give in Overwhelmed with sadness He reached for his gun And took her life along with his Before the morning sun Then there’s John Lennon’s “Mother.” I was going to quote the lyrics when I realized it was the absolutely depths-of-his-soul screams that make the song so tragic. ---
**Author:** ![smilla](https://avatars.discourse-cdn.com/v4/letter/s/48db29/32.png) [@smilla](https://boards.straightdope.com/u/smilla)\ **Post date:** [May 2, 2002, 3:42am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/137 "2002-05-02T03:42:21Z")
Dave Matthews Band (don’t hurt me!)- Pay for What you Get Tori Amos - China Tori Amos(this is a remake) - '97 Bonnie & Clyde Deep Forest - The First Twilight Pizzicato 5 - Sweet Thursday I’ve got a huge case of depressing CDs, and yet I can’t think of sad songs. ---
**Author:** ![Jibby7](https://avatars.discourse-cdn.com/v4/letter/j/65b543/32.png) [@Jibby7](https://boards.straightdope.com/u/Jibby7)\ **Post date:** [May 2, 2002, 4:14am UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/138 "2002-05-02T04:14:41Z")
The two songs that stick out to me off the top of my head are Leader of the Band by Dan Fogelberg (strong personal feelings) and I also think Fields of Gold by Eva Cassidy is pretty damn sad, sadder than Sting’s version. And as a baseball junky forceably retired from the game, This Used to be My Playground by Madonna. ---
**Author:** ![Fluffy](https://avatars.discourse-cdn.com/v4/letter/f/9e8a1a/32.png) [@Fluffy](https://boards.straightdope.com/u/Fluffy)\ **Post date:** [May 2, 2002, 2:08pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/139 "2002-05-02T14:08:21Z")
Without a doubt; ALONE AGAIN NATURALLY (Gilbert OSullivan) This song came out when I was in first grade. I can remember hearing it on the car radio and I would just curl up on the floor of the car in the fetal postion and practically have an anxiety attack! At the age of 5 or 6! This is not exaggeration. DOWNBOUND TRAIN (Bruce Springsteen) ONE STEP UP & TWO STEPS BACK (Bruce Springsteen) One just needs to listen to the lyrics of the Springsteen songs to understand why. ---
**Author:** ![plnnr](https://avatars.discourse-cdn.com/v4/letter/p/7ea924/32.png) [@plnnr](https://boards.straightdope.com/u/plnnr)\ **Post date:** [May 2, 2002, 3:56pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/140 "2002-05-02T15:56:59Z")
Both “She’s Leaving Home” and “Wharf Rat” are positive songs in my book. “She’s Leaving Home” is about a woman who’s been living a stifling, oppressive life and leaves home. The last stanza contains the line “She…is having…fun.” She meets a guy from the motor trade, has a date. Her life is completely transformed. As far as Wharf Rat goes, August West may be a old man asking for spare change for a cup of coffee, but he’s got his spirit left. “I’ll get up and fly away…I’ll get up and fly away…fly away.” \ ---
**Author:** ![Morgainelf](https://avatars.discourse-cdn.com/v4/letter/m/71e660/32.png) [@Morgainelf](https://boards.straightdope.com/u/Morgainelf)\ **Post date:** [May 2, 2002, 6:48pm UTC](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024/141 "2002-05-02T18:48:31Z")
I can’t believe no one has mentioned _How Soon Is Now_ by the **Smiths**. _This_ is by far the saddest song ever. I used to think that _At Seventeen_ by **Janis Ian** was really sad, until I understood the lyrics. It’s totally an in-your-face revenge song. Sample lyrics: > [@](#): > > A brown eyed girl in hand-me-downs > Whose name I never could pronounce > Said, “Pity, please, the ones who serve > They only get what they deserve. > The rich relationed hometown queen > Marries into what she needs > A guarantee of company > And haven for the elderly” > > Remember those who win the game > Lose the love they sought to gain > In debentures of quality > And dubious integrity > The smalltown eyes will gape at you > In dull surprise when payment due > Exceeds accounts received at seventeen Hah! And when I was a kid, _Wildfire_ always made me cry. That poor horse! [Previous page](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024.md?page=6) [Next page](https://boards.straightdope.com/t/what-are-the-saddest-songs-you-know/106024.md?page=8)