1. Nico, "These Days" (available on Chelsea Girl)
Jackson Browne's "These Days" is a world-weary lament that could have been written by Holden Caulfield as he stared dreamily out of a mental-hospital window at the end of The Catcher In The Rye. Like Big Star's "Holocaust," it's a melancholy sigh of a song from someone who's seen far too much of what life has to offer to hold onto anything resembling hope. Not even Nico's Count Chocula-esque accent and tragic-robot delivery can keep the exhausted fragility of "These Days" from subtly but unmistakably working the tear ducts. Remarkably, Browne wrote it while he was still a teen songwriting prodigy learning the ropes from muse/lover Nico and Tim Buckley.
2. Reflection Eternal, "For Women" (available as a bonus track on Train Of Thought)
In "For Women," rapper Talib Kweli reached back into the pantheon of African-American song and offered a hip-hop version of Nina Simone's "Four Women." His poignant, multi-part story-song pays heart-wrenching tribute to four remarkable black women who symbolize the anguish and uplift of multiple generations trying to maintain their self-respect in the face of racism, sexism, and poverty. As with many hip-hop heartbreakers, the production here carries much of the emotion: Hi-Tek's melancholy beat aches with empathy and compassion.
3. The Beach Boys, "'Til I Die" (available on Surf's Up)
Brian Wilson's personal and creative resurgence after years of self-imposed exile is one of rock's great comeback stories, but the Beach Boy's future was very much in doubt in 1971. In his autobiography, Wilson claimed he was so depressed and death-obsessed at the time that he instructed his gardener to dig a grave in the back yard. Wilson poured his emotions into "'Til I Die," a song about humanity's insignificance in the face of the universe. His fellow Beach Boys thought the song was too much of a downer, so Wilson recorded it himself. That's probably just as well—"'Til I Die" is a suicide note that (thankfully) ended up being a false alarm.
4. John Lennon, "Mother" (available on Plastic Ono Band)
John Lennon wrote about his dead mother more than once, but "Julia" took in her memory through rose-colored glasses. "Mother," the lead-off track on Lennon's first post-Beatles solo album, is the angry, nightmarish companion piece. The "seashell eyes" and "windy smile" of "Julia" are set aside—Lennon denounces both of his parents for abandoning him for most of his childhood. "Mother" is devastating because of Lennon's naked hurt as he wails over and over, "Mama don't go, Daddy come home." In the hands of a lesser artist, "Mother" would merely be a rock-star pity party. But Lennon's greatest talent was finding the universal in the personal, and "Mother" digs out listeners' family-related dysfunctions and rubs them raw.
5. Eels, "P.S. You Rock My World" (available on Electro-Shock Blues)
The jolts on Electro-Shock Blues (namely, the deaths of the songwriter's mother and sister) come so fast that there's no choice but to try and mourn with it, which gets pretty oppressive over the course of 45 minutes of album. There are breaks in this million-ton cloud cover, but the closing track, "P.S. You Rock My World," finally lifts it: "Sitting down on the steps at the old post office / The flag was flying at half-mast / And I was thinkin' 'bout how everyone is dying / And maybe it's time to live." The sentiment is as sweet as E ever gets: Everything's still shit, yet there's hope.
6. Beulah, "You're Only King Once" (available on Yoko)
On its first three albums, Beulah draped its pain in shimmering layers of brass and strings; its fourth and last, Yoko, attains jaw-dropping bleakness on "You're Only King Once." For once, there's no whimsical escape from lines like "The stars refuse to shine for you, they do it just to spite / Well, they know you're trying too hard" and "Smile, please smile, I just want you happy." The frustrated character behind so many brilliantly angry Beulah songs has nothing left to comfort him, and it's suddenly very hard to smirk at him.
7. Elliott Smith, "Roman Candle" (available on Roman Candle)
The hallucinatory musings of a longsuffering hostage who can only imagine his revenge, "Roman Candle" is Elliott Smith's calling card—the first song on the first album in a mind-bogglingly rich career best understood as one giant attempt at catharsis. Recorded in a Portland basement under conditions Smith later described as "total autarchy," the track was never intended for public release, but it exists as a primordial soliloquy trapped in the amber of friends' ambitions for his career. Sung in a heavy whisper, the chorus—"I want to hurt him / I want to give him pain"—is just devastating.
8. Bright Eyes, "Going For The Gold" (available on Oh Holy Fools)
This excellent track contains ample ammunition for the anti-Conor Oberst set; it was puzzlingly relegated to a split CD in 2001, when he was 20. The singer-songwriter's cracked voice and weepy acoustic guitar indulge in exactly the kind of self-pity and despair people hate him for. If there's a sadness contest among coffeehouse artisans, the lyrics say, he's winning it—he's the "champion of idiots." But listen through to the last verse, when muted trumpet and weepy flute join in, and Oberst trades the self-doubt for a melancholy celebration of music's power and beauty.
9. Uncle Tupelo, "Still Be Around" (available on Still Feel Gone and 89/93: An Anthology)
One of the alt-country group's most affecting songs glimpses the aftermath of loss with an almost palpable sense of longing. "Still Be Around," which consists of Tupelo co-leader Jay Farrar singing with a 12-string guitar, opens with him on a search: "I don't see you through the windshield / I don't see you in faces looking back me." Unsuccessful, he turns to alcohol, which leads to a self-destructive routine where "the Bible is a bottle and the hardwood floor is home / When morning comes twice a day, or not at all." Farrar needs help out of the muck, but worries that the only person who can help is gone forever.
10. Leonard Cohen, "Famous Blue Raincoat" (available on Songs Of Love And Hate)
Saying "I get teary-eyed over a Leonard Cohen song" is a bit like saying "Coffee perks me up, " since a maudlin pallor hangs over nearly everything the man wrote, even the songs ostensibly about love. In fact, in terms of wallowing in morbidity, "Raincoat" pales in comparison to "Dress Rehearsal Rag," from the same record. Nevertheless, "Raincoat"—structured as a letter of reconciliation between Cohen and an old friend, who was involved in a love triangle with Cohen's woman Jane—is somehow the most emotionally wrenching. The welling of complicated emotions and gentle defeat contained in the lines "I guess that I miss you / I guess I forgive you" gets us every time.
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11. Television Personalities, "Stop And Smell The Roses" (available on The Painted Word)
With The Painted Word, Dan Treacy abandoned the cheeky '60s pop of his band's earlier efforts for something more introspective. As it turned out, the inside of Treacy's head was a harrowing place to be. The entire album drips with themes of alienation and despair, a mood set by this opening track, which drones along like a lost Velvet Underground song on a bed of organ and violin while Treacy halfheartedly tries to fool himself into believing "everything's so lovely," before remembering "You're just so far away / And I don't expect to see you again." It's the kind of song that anyone who's just gone through a painful breakup will play for days on end—so be careful where you leave it lying around.
12. Jawbreaker, "Do You Still Hate Me?" (available on 24 Hour Revenge Therapy)
It's easy to make sad songs slow, but few musicians can craft breakneck anthems that convey heartache and despair better than a plodding ballad would. Jawbreaker's Blake Schwarzenbach was one of them—and among his masterpieces is "Do You Still Hate Me?", a punk uppercut to the ventricles with lyrics as blunt and plainspoken as the title. "Been hearing about you, all about your disapproval / Still I remember the way I used to move you," Schwarzenbach growls regretfully before clutching at a fading memory: "I have a picture of you and me in Brooklyn / On a porch, it was raining / Hey, I remember that day, and I miss you." When tears aren't enough, sometimes you just gotta put your fist through the wall.
13. Morrissey, "The Ordinary Boys" (available on Viva Hate)
Morrissey's solo debut contains lots of mope-tastic moments, but the biggest ("Everyday Is Like Sunday," "Suedehead") have been overplayed to the point of self-parody. Tucked toward the end of the disc, though, is "The Ordinary Boys," a largely ignored track that nails adolescent isolation and gray angst with lines like "Ordinary girls, supermarket clothes / Who think it's very clever to be cruel to you." Whether the Moz is uncloaking his own heart or shrewdly catering to the stereotypical Smiths fan, there's no resisting the song's quiet power—or the weepy strums and swells of overlooked guitar genius Vini Reilly.
14. Rilo Kiley, "Portions For Foxes" (available on More Adventurous)
This lovesick lament doesn't sound especially sad, with its pinging guitars and kicky backbeat. But the frank lyrics—and the resigned way Jenny Lewis sings them—build to a regretful, shattering resolution. Addressing an occasional lover whose charms she can't seem to shake, Lewis describes how, in spite of her friends' warnings, she's compelled to call him up and see what he's doing. And then "The talking leads to touching and the touching leads to sex / And then there is no mystery left." Halfway through the song, her guy goes out tomcatting, but she forgives him because "I do the same thing / I get lonely too." As Lewis moans about how she's "bad news," everyone who's ever been unable to stop themselves from making a romantic mistake has to feel a deep chill.
15. Josh Rouse, "Michigan" (available on Bedroom Classics Vol. 1 and The Smooth Sounds Of Josh Rouse)
This low-key, cumulatively devastating character sketch is sung from the perspective of a young man—gay, according to interviews Rouse has given—writing home to his folks in Wichita from his Uncle Ray's place in Michigan. The letter starts by updating what he and the relatives have been up to. He's bartending, and playing cards during the day with Ray, while Aunt Terry's trying to become a songwriter. In the original acoustic version on Bedroom Classics, Rouse's voice cracks as the narrator gets to the point of why he's writing after being away from home for so long. "Mom, I'm sorry, I was wrong," he sings, explaining that it wasn't his parents' fault that he ran away, but the town's. He ends by saying that he's lonely, but getting along okay. Then he signs off with a line designed to melt the hearts of children and parents alike: "Just trying to be happy. Love, your son."
16. Neil Young, "Harvest Moon" (available on Harvest Moon)
Neil Young has a catalog of simple, beautiful songs and an unmistakable lilt in his voice that naturally quivers with emotion, but "Harvest Moon" stands out as particularly special because it came out in 1992, after he'd weathered the ups and downs of the music industry for more than two decades. Something about the song—a romantic reminiscence on acoustic guitar, with a gentle brush accompaniment—dovetails nicely with Young's career and all the mileage that brought him to that point. In the chorus, phrases like "Because I'm still in love with you" and "I want to see you dance again" suggest a relationship that's come through mileage and hardships, but endures all the same. This song has been used for weddings, but it's probably more appropriate for anniversaries.
17. Dolly Parton, "Coat Of Many Colors" (available on Coat Of Many Colors)
Dolly Parton's sentimental streak has led her to write some godawful songs—witness "Me And Little Andy," in which a little abused girl and her puppy meet untimely ends. But there isn't a misplaced word or an overemphasized note in this autobiographical story from Parton's childhood, in which her mother stitches together a coat from a box of rags while telling young Dolly the biblical story of Joseph and his coat of many colors. To Parton's dismay, the kids at school all make fun of her, but she learns a lesson about the real meaning of wealth, even if they never will. (The original coat now hangs in Parton's Dollywood theme park, but that ought to be beside the point.)
18. Elvis Costello, "Veronica" (available on Spike)
The upbeat bounce of Elvis Costello's peppy rock number (co-written with Paul McCartney) completely belies its sob-worthy story about an elderly woman who "sits very quiet and still," presumably in a nursing home; it's somewhere where no one ever gets her name right, not that it matters, since she no longer recognizes it anyway. Sure, that's sad. But the real killer is Costello's extended word-image of Veronica as a vibrant, active, playful young woman, "65 years ago, when the world was the street where she lived." And as if the contrast between her past and her present wasn't heartbreaking enough, Costello muses over whether that quiet, vacant woman is actually just hiding in a dream of her youth. She's still alive, he implies, but she's as lost to the strangers around her as the knowledge of her long-ago glory days is lost to them. It's all the horror of aging, death, and loss in one cheery pop package.