I could probably spend the entire damn trip writing about the songs that should be included and why I won't include them, so I'll just cut to the chase (this of course is no guarantee that I won't change my mind several times before hitting land again and give you more boring play by play the whole time) and share the final line up with a few comments on the selections:
1) the longest drive - the Capricorns (for the duration of this commentary, I'm not capitalizing most titles of songs and mean nothing by it other than I'm feeling lazy. )
So maybe in the greater universe this isn't one of the saddest songs of all time, but I've been Capricorning myself to death and obsessed with them since the last trip. In listening to them over and over and over and over again on that trip, it struck me how truly sad this song is, which you would never notice if you just went by the frantic electro beat, but when you give it a good listen that frantic pace only seems to reinforce the desperation and loss this song is a record of.
2) the grand tour - George Jones.
As I said before, the man has a voice made for breaking your heart. This isn't his most desperate song but it packs a wallop. "A Good Year for the Rose" might have edged this one out if I had it in my library.
3) golden ring - Tammy Wynette and George Jones.
Again, I've already discussed why this song is so pointed. You are probably thinking to yourself that I'm not really going to break anyone's heart with my song selection so far, and that might be true, particularly since I imagine my main audience to be comprised of cold hearted bastards (which you must all be since no one ever leaves comments. Of course this assumes an audience...).
4) miss being mrs. - Loretta Lynn.
Too damn beautiful for words. So simple and to the point, just laying out flat how she is missing her husband. No embellishment, just direct and lovely phrasing.
5) letter to mom - Iris Dement.
Enough of just sad, let the soul crushing begin. If she wanted to sing it sad, Iris Dement could make you cry with "Jingle Bells"; there is just something in that voice. If she, Nanci Griffith, Emmylou Harris, and Gillian Welch brought their voices together, what hell they could cause. Throw in Lucinda Williams and the vocal combination could destroy us all if they decided it was time for us to cry. They each have a different kind of gorgeous warble that can either make you think of angels or just rip your fucking heart out. Iris is kind of the most punk of them all, with the most unruly voice which can sound so childishly innocent but always barely holding back this ethereal growl. She (particularly with any combination of the above women) could make the most amazing Southern gothic rock opera album. Let's imagine it with all of them...
I'm getting off track. I'll plan out my fictional world where I decide who sings what songs later. Back to sad songs and Iris crushing our souls. "Our Town" might be sadder in a way; it is certainly more defeated, but this song is so wrenching it is hard to believe it was even written much less sung and, having been sung, that it was sung by this voice. It starts so friendly but the subject matter... holy shit. (note: in the liner notes from this album, Ms. Dement points out that this is not autobiographical, but she did write it to help her process a story told her by a friend.)
You could argue that this song is too upbeat sounding or too defiant or...no, listen to it again and cry some tears.
6) six o'clock in the morning - ?
I don't know who the artist is. I can't remember for the life of me and have lost all the other songs I had by him, but I remember all the ones that I had were somehow in this same vein of wow-life-is-miserable-but-you-have-to-trudge-on. It is just sort of plodding misery and the weight of life's futility piling on instead of any one tragedy. Instead it focuses on that horrible moment of any routine day -getting out of bed- and treats it as the Sisiphean task that it is.
7) one more dollar - Gillian Welch.
One more soul-crushed-by-daily-life, there-but-for-the-grace-of song. Something in this song is so sad to me. I listen to it and cringe (and then listen to it again).
8) cold missouri waters - Richard Shindell with Dar Williams and Lucy Kaplanski.
This is cheating. This is from the album Cry Cry Cry which was made by these three sadists for the express purpose of collecting tear jerking tunes. But I don't care. The atmosphere in the song, the way the story is shared, the death bed confessional of it all. So damn amazing. Just a good plain sad song.
9) lonlier than this - Steve Earle.
Steve Earle can write a fucking song. And though he does great rebel songs and love songs, his sad songs are pretty hard to beat. I love this song. From the first time I heard it, I was mesmerized by the direct wallowing of it all. "It doesn't get any lonlier than this," is a pretty bold statement but he catches that emotion that makes that statement seem truly pained and sincere rather than hokey. I love singing this song, but Mason blatantly refuses to play it ever on account of it being too sad (this is from someone whose favorite song to sing in "Long Black Veil").
10) travelling soldier - Dixie Chicks.
I wanted to include "Am I the Only One", which is one of my all-time faves, but somehow in all these other songs its existential howl seemed too far away. "When You Were Mine" was a close second, but for just sheer complete and utter sad-songness this one can't really be beat. Natalie Maines has the voice to deliver it, and the story is so sweet then so lonely and hurt. It starts so pretty and you kind of have a moment when you know it is going to turn bad, but really, the image of the lonely girl in her band uniform crying under the bleachers while no one else cares is so insanely heart breaking.
11) ruby, don't take your love to town - Kenny Rogers and The First Edition.
The groovy back beat and finger picking makes the song sound amazing in a way that it is easy to forget some old country songs used to sound. But Kenny's quiet pleading in the song contrasts that so perfectly. It can't be just a man wishing his woman would do right by him; it has to be a song about a crippled vet watching his woman slip away from him because of his war injury as he lies there slowly dying. Don't hold back now. Of course, the song most likely to make anyone anywhere cry is Rogers' "The Coward of the County" and I haven't forgotten this, but I figured one rape song is enough for any list and anyway in the end of that song, you get revenge and get to feel an explosive surge of everything-is-right-in-the-world that kind of nullifies the pure sad-songness of it all. (Note to Kenny on the off chance that he ever reads this: drop the 'touching' mellow adult contemporary stuff for a while and make a kick-ass rough-around-the-edges album. And do a duet with Dolly on it. In a perfect world, the duet would be a cover of the Mountain Goats' "No Children" a la Kiki and Herb).
12) if we make it through december - Merle Haggard.
Just one of the most heart breaking songs ever. Not woe-is-me-my-baby-left-me or any crap like that, but a poor man being crushed by not being able to provide for his family at Christmas time.
13) martha - Tom Waits.
I've already written extensively about this song, so I won't beat a dead horse. Just so beautiful and sweetly sad. Tear-jerkers don't have to all be soul crushing.
14) getting over you - Janice Ian.
The way this woman writes and the way she sings... damn! "At Seventeen" could have been here, but teenage misery only deserves so much sympathy, even when it is captured so perfectly. And this is just so sad. From the first moment you hear the voice in the song, there is this tension of "I'm fine, no problem" and just-about-to-lose-it. There is that moment when she sings "You want answers that I can't give; you want words I don't know!" where her voice explodes at "know" and does something that gives me chills. The phrase is powerful enough and then she has to do that thing with her voice and it blows my mind every time.
15) red dirt girl - Emmylou Harris.
Again, one of these warbly angel voices that can kill. Of all my beautiful tremulous ladies, Ms. Harris's voice is completely other-worldly. Almost too hypnotic to break your heart at times, because you can get so lost in it, but this song kills me. Maybe it hits me all the harder since it is set in my landscape. Red-clay Alabama is my homeland, and there is something about that dirt that gets to you. That may seem like a dumb thing to say, but... I don't feel like discussing the affect of the soil on the mood of the landscape from my childhood. Let's just say when she sings about a red-dirt girl, it has immediate impact for me and there is built in tragedy in that landscape and the story in the songs fits perfectly. I wonder if I'd feel the same about the song if I were from somewhere else.
16) billy grey - Robert Earl Keen, Jr.
Just a plain beautiful tragic love song. This man doesn't get near enough credit as either a song writer or singer. Something in this song always gets me.
17) ruby's arms - Nanci Griffiths.
So Iris can growl and Emmylou can make you feel like you are in a legend, but for just breaking your heart straight out, nobody's got nothing on Nanci. Something in her voice cuts like a knife. This song is kind of pleasant and billowy, but the sadness is so overwhelming. It is one of those songs where I start wanting to pick it apart as I listen and scream at the protagonist not to leave, to question motives and all that crap, but her voice pushes that away and I'm just left with no doubt that he has to leave, that he truly loves her, that he can never turn back and I accept it all kind of soothingly, but then Nanci sings "Jesus Christ, this cold hard rain; won't someone put him on his train?" And my heart breaks right down the middle.
18) sweet loraine - Patty Griffin.
This is the first song by Patty Griffin that caught my attention. When I was in college in Charleston, the local music store had listening stations and I used to go between classes sometimes and just bury myself in songs. This album was up for a while and I listened to this song over and over and over again. It blew my mind everytime. It still does. The little phrases in the song are the ones that kill you. "Her mother threw stones at her on the day she moved. Now isn't that a funny thing to do, from someone who never really wanted you?" and "Her daddy calls her a slut and a whore on night before her wedding day; the very next morning, at the church, her daddy gave Lorraine away." would be gut wrenching by themselves, but again we've got a singer here who makes you feel it.
19) anymore - Travis Tritt.
This almost feels cheesy next to "Sweet Lorraine" but Mr. Tritt can deliver sad and be believable in a way that too many of "Today's Hottest Country" artists can't. I would just consider this a nice sad song, but I've got the indelible memory of the video attached to it. He had this series of relentlessly heartbreaking videos to go along with his songs and this was the clincher (if I'm remembering correctly). In this one, he is a wheel-chair bound vet whose best friend is an old black man who walks with a cane, who is working on his boat when his very pregnant wife brings him a snack, slips on the boat, hitting her head as she falls into the water. He crawls out of his wheelchair and sprawls helplessly on the dock reaching for her in the water as his old friend wades into the water to pull her to safety. She dies, but the baby lives for him to raise alone. The song is being sung as he his preparing to explain to his now adolescent daughter how her mother died. The video ends with them pulling up in their boat to the place where the mother is buried and his daughter turning to him and saying "Why do we always come here on my birthday, Daddy?" It sounds too schlocky to stand, but somehow they pulled it off without making seem like a farce and basically just pile as much tear-jerk as can fit in one video. The song by itself is sad and beautiful, but the memory of that video won its place in my mix.
(update: note that in the comments, some kind person corrects my memory, pointing out that the video I described remembering above was "Tell Me I Was Dreaming". This was actually a video trilogy, with "Anymore" showing him in the VA hospital, becoming friends with the black guy, trying to push his wife away and finally breaking down and returning her call and finding her still in love with him. She takes him home and every -including you- cries and smiles. The end of the trilogy with him taking the little girl to her mother's grave is chronicled in "If I Lost You". To make sure I got it straight this time, I just re-watched all three videos and had my heart smashed to bits again. Do not watch these unless you really want to cry.)
20) sometimes i still feel the bruise - The Mountain Goats.
Again, I've already covered this song ad nauseum so I won't recap here. Go read the other post.
21) You'll Never Leave Harlan Alive - Patty Loveless.
It isn't a warble that makes Patty Loveless's voice so deadly, but there is such unbelievable power in her voice. And few people can sing sad like she can. There are a couple of other songs from the same album which are heart breakers, but this song still stands out. The story is beautiful and tragic, but the whole sound of it kills you. If it didn't have words and she were just singing the sounds you would still get your heart destroyed by this song. You don't need the words. More than any other song on this list, it just sounds tragic. Brad Paisly also recorded this song, and I can't imagine what he was thinking. Actually, I can. It is a beautiful song and who wouldn't want to sing it? But damn, the list of people who could do it justice after this version is a very, very short list and Paisly is a great entertainer but only a good singer. Raul Malo or Toby Keith or Dwight Yoakam might be able to make a passable swipe at it, but still...
22) he was a friend of mine - Willie Nelson.
It is no secret that I love Willie Nelson. Obsessively. But all that aside, this song is a killer. So quietly sad. And this isn't a song that is easy to sing (try sing along for a minute. I'll wait), but Willie's voice captures something so perfectly here. The song has this tremendous potential, but without the right voice it would be nothing special. The lyrics are kind of repetitious and bland, which are strengths the way it is sung here, but in different hands you would just have a plodding, pleading yelp. Oddly enough, I have three versions of the song on my computer. Cat Power does ok with it. Nothing special. And I've got Mercury Rev doing it. They do a suprisingly good job with it, but the song just doesn't break your heart without Willie wielding it.
Anyway, that's gone on long enough. If anyone has good sad song suggestions, I'm always looking for some tear-inducing heartbreakers.