# Your most painfully beautiful song **URL:** \ **Category:** Cafe Society\ **Created:** [January 31, 2008, 9:11am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698 "2008-01-31T09:11:45Z")\ **Posts on this page:** 20\ **Page:** 3
**Author:** ![Plynck](https://avatars.discourse-cdn.com/v4/letter/p/3e96dc/32.png) [@Plynck](https://boards.straightdope.com/u/Plynck)\ **Post date:** [January 31, 2008, 8:02pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/41 "2008-01-31T20:02:18Z")
Patty Griffin’s Rain from 1000 Kisses: \*It’s hard to listen to a hard hard heart Beating close to mine Pounding up against the stone and steel Walls that I won’t climb Sometimes a hurt is so deep deep deep You think that you’re gonna drown Sometimes all I can do is weep weep weep With all this rain falling down Strange how hard it rains now Rows and rows of big dark clouds When I’m holding on underneath this shroud Rain\* ---
**Author:** ![SylverOne](https://avatars.discourse-cdn.com/v4/letter/s/c0e974/32.png) [@SylverOne](https://boards.straightdope.com/u/SylverOne)\ **Post date:** [January 31, 2008, 8:15pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/42 "2008-01-31T20:15:57Z")
**Kathy Mattea’s** song _Where’ve You Been_ > [@](#): > > They’d never spent a night apart > For sixty years she heard him snore > Now they’re in a hospital > In separate beds on different floors > Claire soon lost her memory > Forgot the names of family > She never spoke a word again > Then one day, they wheeled him in > He held her hand and stroked her hair > In a fragile voice she said, > "Where’ve you been? > I’ve looked for you forever and a day > Where’ve you been? > I’m just not myself when you’re away. I’m fine until the last verse, then I’m a bawling idiot. ---
**Author:** ![Satellite\_Guy](https://avatars.discourse-cdn.com/v4/letter/s/258eb7/32.png) [@Satellite\_Guy](https://boards.straightdope.com/u/Satellite_Guy)\ **Post date:** [January 31, 2008, 8:16pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/43 "2008-01-31T20:16:30Z")
I posted this one in the “most depressing songs” thread, but I think it’d be much more appropriate for this one; Billy Falcon – Heaven’s Highest Hill [![]( " - YouTube") ](https://www.youtube.com/watch?v=r1UMlGWFBWo) S^G ---
**Author:** ![jjimm](https://avatars.discourse-cdn.com/v4/letter/j/ba8739/32.png) [@jjimm](https://boards.straightdope.com/u/jjimm)\ **Post date:** [January 31, 2008, 8:18pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/44 "2008-01-31T20:18:06Z")
While we’re on a Sinéad O’Connor trip, her version of [Silent Night](http://www.youtube.com/watch?v=87q5dmW6zDg) is guaranteed to make evey Christmas a heartbreak. ---
**Author:** ![Glory](https://avatars.discourse-cdn.com/v4/letter/g/7cd45c/32.png) [@Glory](https://boards.straightdope.com/u/Glory)\ **Post date:** [January 31, 2008, 8:32pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/45 "2008-01-31T20:32:37Z")
Currently, it’s A Comet Appears by The Shins \*We can blow on our thumbs and posture, But the lonely is such delicate things, The wind from a wasp could blow them, Into the sea, With stones on their feet, Lost to the light and the loving we need, Still to come, The worst part and you know it, There is a numbness, In your heart and it’s growing\* ---
**Author:** ![gigi](https://avatars.discourse-cdn.com/v4/letter/g/a587f6/32.png) [@gigi](https://boards.straightdope.com/u/gigi)\ **Post date:** [January 31, 2008, 8:35pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/46 "2008-01-31T20:35:55Z")
**Remember When** by Alan Jackson _remember when, the sound of little feet was music_ I heard it last night and was thinking of starting a thread on Most Perfect Song ever but realized mine are all perfect because they are painfully beautiful. So this thread is timely! Also **Lies** by Stan Rogers \*is this the face that won for her the man, whose amazed and clumsy fingers put that ring upon her hand? she’ll look up in that weathered face that loves hers line for line, and see that maiden shining in his eyes\* **Goodnight Saigon** by Billy Joel ---
**Author:** ![Satellite\_Guy](https://avatars.discourse-cdn.com/v4/letter/s/258eb7/32.png) [@Satellite\_Guy](https://boards.straightdope.com/u/Satellite_Guy)\ **Post date:** [January 31, 2008, 8:59pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/47 "2008-01-31T20:59:41Z")
[QUOTE=gigi] **Lies** by Stan Rogers \*is this the face that won for her the man, whose amazed and clumsy fingers put that ring upon her hand? she’ll look up in that weathered face that loves hers line for line, and see that maiden shining in his eyes\* [/QUOTE] I’m a Stan Fan, and I’ve always loved that song, and agree whole-heartedly. I find many of his songs could fit into this category, because he often writes about the hardships of life of Everyman, so many people can relate on one level or another – -Make & Break Harbour -Sailor’s Rest -The Field Behind The Plow -White Squall … and many others S^G ---
**Author:** ![Omega\_Glory](https://avatars.discourse-cdn.com/v4/letter/o/7c8e57/32.png) [@Omega\_Glory](https://boards.straightdope.com/u/Omega_Glory)\ **Post date:** [January 31, 2008, 9:19pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/48 "2008-01-31T21:19:41Z")
Honey and the Moon- Joseph Arthur [![](https://i.ytimg.com/vi/NJEZWNF845o/hqdefault.jpg "Audrey Hepburn") ](https://www.youtube.com/watch?v=NJEZWNF845o) Here’s a clip (that also happens to be a tribute to Audrey Hepburn). Fast Car- Tracy Chapman. The girl starts out full of hope, just to end up in the same circumstances that she tried to escape. [QUOTE=Drain Bead] “Lover, You Should’ve Come Over” by Jeff Buckley [/QUOTE] Good choice. This one is made even worse when you consider that he’s gone. ---
**Author:** ![Baron\_Greenback](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/baron_greenback/32/48_2.png) [@Baron\_Greenback](https://boards.straightdope.com/u/Baron_Greenback)\ **Post date:** [January 31, 2008, 9:27pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/49 "2008-01-31T21:27:39Z")
Nick Cave - [The Ship Song](http://www.youtube.com/watch?v=rKlaV-9Vzsk) is very beautiful, and is personally painful. ---
**Author:** ![Khampelf](https://avatars.discourse-cdn.com/v4/letter/k/8e7dd6/32.png) [@Khampelf](https://boards.straightdope.com/u/Khampelf)\ **Post date:** [January 31, 2008, 9:30pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/50 "2008-01-31T21:30:39Z")
Ditto on the Dire Straights ‘Romeo and Juliet’ and ‘Don’t Give Up’ by Gabriel and Bush. Mine is ‘Kryptonite’ by Three Doors Down. ---
**Author:** ![Ichbin\_Dubist](https://avatars.discourse-cdn.com/v4/letter/i/51bf81/32.png) [@Ichbin\_Dubist](https://boards.straightdope.com/u/Ichbin_Dubist)\ **Post date:** [January 31, 2008, 10:18pm UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/51 "2008-01-31T22:18:51Z")
Of late, “Asleep and Dreaming” by Magnetic Fields: _Well you may not be beautiful But it’s not for me to judge I don’t know if you’re beautiful Because I love you too much_ If you like the Arvo Pärt piece mentioned above, I’ll toss in the cellos-only version of “Fratres.” ---
**Author:** ![threnodyangelfire](https://avatars.discourse-cdn.com/v4/letter/t/ecc23a/32.png) [@threnodyangelfire](https://boards.straightdope.com/u/threnodyangelfire)\ **Post date:** [February 1, 2008, 12:54am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/52 "2008-02-01T00:54:18Z")
> [@](#): > > Mine is ‘Kryptonite’ by Three Doors Down. That film clip makes me cry with the poor old fellow in the superhero costume. I just feel so sorry for him because he seems so lonely… Making Gravy, by Paul Kelly One Crowded Hour, by Augie March ---
**Author:** ![Gangster\_Octopus](https://avatars.discourse-cdn.com/v4/letter/g/a8b319/32.png) [@Gangster\_Octopus](https://boards.straightdope.com/u/Gangster_Octopus)\ **Post date:** [February 1, 2008, 1:01am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/53 "2008-02-01T01:01:46Z")
_In My Arms_ by Nick Cave, because the song is amazing and because it is the song my wife and myself danced to at our wedding. ---
**Author:** ![Darth\_Sensitive](https://avatars.discourse-cdn.com/v4/letter/d/58956e/32.png) [@Darth\_Sensitive](https://boards.straightdope.com/u/Darth_Sensitive)\ **Post date:** [February 1, 2008, 1:24am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/54 "2008-02-01T01:24:11Z")
I curse whoever brought up ‘Remember When’ by Alan Jackson in the Depressing song thread yesterday. I was listening, and just broke down. It was part of the traditional Homecoming pep rally slow cheer which sounds kinda dumb, and I thought it was too, till I was a senior. That song brings back Friday nights out at the football field, cheering as hard as I could and wearing my letter jacket and screwing around in class and making a senior mum that I was proud of and that game being a first date and friends at different colleges who I don’t see and knowing I fit in with just about everyone. I don’t miss a whole lot of things about high school, but that song last night made me think of all the good things. [![]( " - YouTube") ](https://www.youtube.com/watch?v=2Y4NTXT96EM) ---
**Author:** ![Boyo\_Jim](https://avatars.discourse-cdn.com/v4/letter/b/87869e/32.png) [@Boyo\_Jim](https://boards.straightdope.com/u/Boyo_Jim)\ **Post date:** [February 1, 2008, 1:30am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/55 "2008-02-01T01:30:55Z")
_Leavin’ on a Jet Plane_ by Peter, Paul and Mary ---
**Author:** ![ignis\_glaciesque](https://avatars.discourse-cdn.com/v4/letter/i/5f8ce5/32.png) [@ignis\_glaciesque](https://boards.straightdope.com/u/ignis_glaciesque)\ **Post date:** [February 1, 2008, 1:31am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/56 "2008-02-01T01:31:15Z")
[QUOTE=Freudian Slit] The Kurt Weill song, “September Song.” The version I know and love is by Lou Reed. [/QUOTE] I gotta second that one. I listened to that song a lot when I was young and first fell in love (it was unrequited, making it even more poignant). Up to about two weeks ago, my heartbreak song was a Swedish folksong by the name of _Vem Kan Segla Förutan Vind_ (Who Can Sail Without the Wind?). You see, last November, I took a little vacation in Sweden to visit my girlfriend, who was studying there for the semester. I had planned to sing that to her on parting, as a ridiculously sappy romantic gesture (and to show off how quickly I was learning Swedish), but wouldn’t ya know — we broke up instead, the very last morning I was there. Ouch. ---
**Author:** ![Rysdad](https://avatars.discourse-cdn.com/v4/letter/r/7cd45c/32.png) [@Rysdad](https://boards.straightdope.com/u/Rysdad)\ **Post date:** [February 1, 2008, 1:50am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/57 "2008-02-01T01:50:26Z")
[QUOTE=Liberal] Two for me: **Angel** - Sarah McLachlan, played at our grandson’s funeral [/QUOTE] Yeah. OK. Oh, Christ. That’s too sad to even think about. My condolences. ---
**Author:** ![Infovore](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/infovore/32/420_2.png) [@Infovore](https://boards.straightdope.com/u/Infovore)\ **Post date:** [February 1, 2008, 3:17am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/58 "2008-02-01T03:17:14Z")
Schmaltzy, I know, but two songs that do it to me are _It Was a Very Good Year_ by Frank Sinatra and _When October Goes_ by Barry Manilow. Same basic idea–the bittersweet feeling that comes with getting older. ---
**Author:** ![Cat\_Whisperer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cat_whisperer/32/4839_2.png) [@Cat\_Whisperer](https://boards.straightdope.com/u/Cat_Whisperer)\ **Post date:** [February 1, 2008, 4:06am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/59 "2008-02-01T04:06:09Z")
“The Dance” by Prince. I could probably list about 50 Prince songs that are painfully beautiful just based on his voice - a technically gorgeous voice, and damn he knows how to use it. “Worlds Apart” by Vince Gill. “Hurt” by Christina Aguilera. I like k.d. lang’s version of “Hallelujah” better than anyone else’s. ---
**Author:** ![Nzinga\_Seated](https://avatars.discourse-cdn.com/v4/letter/n/b5ac83/32.png) [@Nzinga\_Seated](https://boards.straightdope.com/u/Nzinga_Seated)\ **Post date:** [February 1, 2008, 4:42am UTC](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698/60 "2008-02-01T04:42:43Z")
I had my friend put Hallelujah on my ipod, and I was very disapointed to realize he thought I meant Jeff Buckley. I needed the beautiful piano of the Rufus Wainright version. Summertime by the great Lady Ella Fizgerald and Lois Armstrong. [Previous page](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698.md?page=2) [Next page](https://boards.straightdope.com/t/your-most-painfully-beautiful-song/435698.md?page=4)