# What's the saddest song on your playlist? **URL:** \ **Category:** Cafe Society\ **Created:** [December 16, 2016, 3:47pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858 "2016-12-16T15:47:19Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![Skammer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/skammer/32/143_2.png) [@Skammer](https://boards.straightdope.com/u/Skammer)\ **Post date:** [December 16, 2016, 3:47pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/1 "2016-12-16T15:47:19Z")
If you ever see my driving down the street with tears streaming down my face and into my gray beard, it’s because this damn song came up in my playlist again: [“The Night I Learned How Not to Pray,” Iris Dement](https://youtu.be/RpRrIlQNqCo) If you don’t have a song that literally makes you cry like a baby ever time, which one at least makes your eyes a little misty? ---
**Author:** ![kenobi\_65](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/kenobi_65/32/13178_2.png) [@kenobi\_65](https://boards.straightdope.com/u/kenobi_65)\ **Post date:** [December 16, 2016, 4:09pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/2 "2016-12-16T16:09:49Z")
Roy Orbison’s “[In The Real World](https://www.youtube.com/watch?v=c-8Fxu8TEH0).” It’s a sad song as it is (being Roy, and all), but due to its personal relevance to me, it makes me cry every time I hear it. ---
**Author:** ![Skammer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/skammer/32/143_2.png) [@Skammer](https://boards.straightdope.com/u/Skammer)\ **Post date:** [December 16, 2016, 4:15pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/3 "2016-12-16T16:15:52Z")
I think the Dement song kills me because of the double tragedy: first, the family loses her baby brother, which breaks my heart as a parent. Then, instead of finding comfort in God, the tragedy understandably drives her away from God, which breaks my heart for her. Plus Iris just has that perfect, unique voice of hers that makes every song poignant. _That was the night I learned how not to pray Because God does what God wants to anyway_ ---
**Author:** ![Paintcharge](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/paintcharge/32/7946_2.png) [@Paintcharge](https://boards.straightdope.com/u/Paintcharge)\ **Post date:** [December 16, 2016, 4:43pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/4 "2016-12-16T16:43:49Z")
[White Winos](https://www.youtube.com/watch?v=MJRERIEbg3c) by Loudon Wainwright. ---
**Author:** ![TroutMan](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/troutman/32/6721_2.png) [@TroutMan](https://boards.straightdope.com/u/TroutMan)\ **Post date:** [December 16, 2016, 5:17pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/5 "2016-12-16T17:17:54Z")
[Daddy Needs a Drink](https://www.youtube.com/watch?v=k_GdEjMv1Ms) by Drive-By Truckers. It exudes hopelessness, and I think most people can see themselves in it at certain points of life. ---
**Author:** ![Just\_Asking\_Questions](https://avatars.discourse-cdn.com/v4/letter/j/ba9def/32.png) [@Just\_Asking\_Questions](https://boards.straightdope.com/u/Just_Asking_Questions)\ **Post date:** [December 16, 2016, 5:24pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/6 "2016-12-16T17:24:52Z")
Without You (Harry Nillson version specifically). The two people that wrote it both committed suicide, and I think Nillson really captured the emotions they put into it. ---
**Author:** ![Sefton](https://avatars.discourse-cdn.com/v4/letter/s/5daacb/32.png) [@Sefton](https://boards.straightdope.com/u/Sefton)\ **Post date:** [December 16, 2016, 5:27pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/7 "2016-12-16T17:27:25Z")
[Angels](https://www.youtube.com/watch?v=7LN-mg_5GGM) by Robbie Williams - “And when love is dead, I’m loving angels instead” ---
**Author:** ![Jackmannii](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/jackmannii/32/311_2.png) [@Jackmannii](https://boards.straightdope.com/u/Jackmannii)\ **Post date:** [December 16, 2016, 5:31pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/8 "2016-12-16T17:31:56Z")
I guess “Over You” by Paul Revere and the Raiders qualifies as sad, at least initially: \*"There’s a-gonna be some slow, slow walkin’ There’s gonna be some sad sad talkin’ There’s gonna be some flower bringin’ There’s gonna be some sad sad singin’ Over you, child, wo, I said over you Hey, hey, oh baby, if I ever hear you say we’re through… Oh, there’ll be a hole about 6 feet deep For you, baby, to take your sleep Into a coffin and a-down you go And you will stay there, sleet or snow… Wo, gonna kill you, baby Tell me what I’ll do, what I’ll do Oh baby, if I ever hear you say we’re through, wow\* :eek: ---
**Author:** ![cochrane](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cochrane/32/10441_2.png) [@cochrane](https://boards.straightdope.com/u/cochrane)\ **Post date:** [December 16, 2016, 5:33pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/9 "2016-12-16T17:33:34Z")
I’ve got a couple. “What Do I Do With My Heart?” by the Eagles. The late Glenn Frey’s voice has never been on better display than in this song. It reminds me that we have lost not only a great tunesmith, but also a helluva singer. “Never Without You” by Ringo Starr. A tribute to his fellow Beatle, the late George Harrison. \*And your song will play on without you And this world won’t forget about you Every part of you was in your song Now we will carry on… Never Without you Within you without you Here comes the song it’s about you I know all things must pass\* ---
**Author:** ![nightshadea](https://avatars.discourse-cdn.com/v4/letter/n/7ba0ec/32.png) [@nightshadea](https://boards.straightdope.com/u/nightshadea)\ **Post date:** [December 16, 2016, 5:43pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/10 "2016-12-16T17:43:11Z")
when the angels sing by social distortion its the ultimate funeral song … ---
**Author:** ![silenus](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/silenus/32/166_2.png) [@silenus](https://boards.straightdope.com/u/silenus)\ **Post date:** [December 16, 2016, 5:49pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/11 "2016-12-16T17:49:41Z")
Without delving into all of my music… “Guenevere” from the musical _Camelot_: _In that dawn, in that gloom More than love met its doom In the dying candle’s gleam Came the sundown of a dream Guenevere, Guenevere In that dim, mournful year Saw the men she held most dear Go to war for Guenevere_ ---
**Author:** ![Robot\_Arm](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/robot_arm/32/18280_2.png) [@Robot\_Arm](https://boards.straightdope.com/u/Robot_Arm)\ **Post date:** [December 16, 2016, 5:51pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/12 "2016-12-16T17:51:39Z")
[Main and Broadway](https://youtu.be/z69LX791Y7E), a bitterly wistful breakup song by a Canadian trio called Cub. _Love letters, broken lockets, Dead flowers, candy boxes, That’s what you’re left with when it’s over_ ---
**Author:** ![Biotop](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/biotop/32/321_2.png) [@Biotop](https://boards.straightdope.com/u/Biotop)\ **Post date:** [December 16, 2016, 5:57pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/13 "2016-12-16T17:57:59Z")
[Coil–“Heartworms.”](http://m.youtube.com/watch?v=XreSoXWP3a4) The singer, Jon Balance, died after falling from a balcony while drunk. ---
**Author:** ![astorian](https://avatars.discourse-cdn.com/v4/letter/a/ad7895/32.png) [@astorian](https://boards.straightdope.com/u/astorian)\ **Post date:** [December 16, 2016, 6:06pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/14 "2016-12-16T18:06:45Z")
Ronnie Drew’s rendition of “The Band Played Waltzing Mathilda” [![](https://img.youtube.com/vi/R2wK-5RxGG4/hqdefault.jpg "Dubliners Waltzing Matilda : Eric Bogle : Anzacs Gallipoli") ](https://www.youtube.com/watch?v=R2wK-5RxGG4) ---
**Author:** ![Tangent](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/tangent/32/3098_2.png) [@Tangent](https://boards.straightdope.com/u/Tangent)\ **Post date:** [December 16, 2016, 6:07pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/15 "2016-12-16T18:07:20Z")
_[My Immortal](https://www.youtube.com/watch?v=5anLPw0Efmo)_, by Evanescence _You used to captivate me by your resonating light Now, I’m bound by the life you left behind Your face it haunts my once pleasant dreams Your voice it chased away all the sanity in me These wounds won’t seem to heal, this pain is just too real There’s just too much that time cannot erase_ _[Break My Heart Sweetly](https://www.youtube.com/watch?v=tNCabzJ8KJI)_, by John Moreland \*There’s a scar on my soul, so let me down easy Break my heart sweetly, like you always do I guess I can’t let go til you wreck me completely Break my heart sweetly, drape me in blue \* ---
**Author:** ![Lsura](https://avatars.discourse-cdn.com/v4/letter/l/7993a0/32.png) [@Lsura](https://boards.straightdope.com/u/Lsura)\ **Post date:** [December 16, 2016, 6:50pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/16 "2016-12-16T18:50:53Z")
[Waiting on June](https://www.youtube.com/watch?v=XUH8VszQun8) ---
**Author:** ![Teuton](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/teuton/32/3864_2.png) [@Teuton](https://boards.straightdope.com/u/Teuton)\ **Post date:** [December 16, 2016, 6:52pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/17 "2016-12-16T18:52:15Z")
[Johnny Cash’s Hurt cover.](https://www.youtube.com/watch?v=vt1Pwfnh5pc) I generally have to be watching the video as well, but it does get me choked up. ---
**Author:** ![gigi](https://avatars.discourse-cdn.com/v4/letter/g/a587f6/32.png) [@gigi](https://boards.straightdope.com/u/gigi)\ **Post date:** [December 16, 2016, 6:59pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/18 "2016-12-16T18:59:12Z")
**How Can I Help You Say Goodbye** breaks me up now that my mom is dead. Also, **Gulf Coast Highway** because I heard it a lot right after she died. And when she dies she says she’ll catch some blackbird’s wing Then she will fly away to Heaven come some sweet blue bonnet spring ---
**Author:** ![Thudlow\_Boink](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/thudlow_boink/32/320_2.png) [@Thudlow\_Boink](https://boards.straightdope.com/u/Thudlow_Boink)\ **Post date:** [December 16, 2016, 6:59pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/19 "2016-12-16T18:59:57Z")
[My Hand To God](https://www.youtube.com/watch?v=-Czj5xtpHvE) by Daniel Amos In this, the closing track of a concept album about a fictional couple named Bud and Irma Ackendorf, Bud is on his deathbed saying his last goodbye to his beloved wife. ---
**Author:** ![journeyman\_southpaw](https://avatars.discourse-cdn.com/v4/letter/j/5e9695/32.png) [@journeyman\_southpaw](https://boards.straightdope.com/u/journeyman_southpaw)\ **Post date:** [December 16, 2016, 7:07pm UTC](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858/20 "2016-12-16T19:07:20Z")
Springsteen - [Stolen Car](https://www.youtube.com/watch?v=eS7tat0J5qQ). (Runners-up include Joni Mitchell - River, Jackson Browne - Before the Deluge, Dire Straits - Romeo and Juliet, Queen - Save Me, Pink Floyd - The Gunner’s Dream.) [Next page](https://boards.straightdope.com/t/whats-the-saddest-song-on-your-playlist/774858.md?page=2)