The album cover:

A close-up shot of the 25-year old (again with the boy geniuses) Ryan Adams, who appears to be wasted (given that he was notorious for his drug and alcohol problems at the time, he’s probably not acting) and lying on a white tablecloth, lit cigarette between his lips, ashtray just beyond the smoke. The album was released on September 5, 2000, and was Adams’ first solo effort, coming on the heels of the dissolution of Whiskeytown, the band which Adams fronted and which has been referred to by some (along with Uncle Tupelo) as the Nirvana of alt-country. Said dissolution came, in large part, due to Adams’ substance abuse problems and his sometimes prickly personality.

The album title:

Adams has been quoted as saying that his manager called him on the phone and gave him fifteen seconds to come up with a title for the album. He happened to be looking at a poster of Mariah Carey wearing a t-shirt that said “Heartbreaker” and voila, he had an album title.

Really, Ryan, what were you doing when you were looking at this?

While I don’t doubt Adams’ story, the truth surely runs a bit deeper. The tone of the songs, as we’ll get into shortly, ranges from somber to downright suicidal. It’s a quintessential get-drunk-by-yourself breakup album, and much of it was supposedly inspired, according to this great profile piece, by Adams’ breakup with his then-girlfriend, a music industry publicist named (track four!) Amy. While Amy is the most likely source of the album title, the album also came out after Adams had failed at his first shot living in New York City. In this story he recalls driving away from the city and seeing the lights through the rear window, an experience that I can attest is quite a heartbreaker in its own right.

The first sound you hear:

A single strike on the muted strings of a guitar, followed by David Rawlings, the guitar virtuoso partner of Gillian Welch, both of whom appear on various songs throughout the album, saying, “Nah, Bona Drag.” The next thirty seconds records Adams and Rawlings arguing over, and eventually betting five bucks on, whether Morrissey’s solo debut single, Suedehead, is found on the album Viva Hate or the compilation Bona Drag. Rawlings doesn’t think it’s on Viva Hate, whereas Adams (correctly) contends it’s on both. (Although Adams is wrong in saying “It’s the sixth track on Viva Hate”; it’s number seven.)

I have two theories for why this is the album intro: a) Adams is a serious geek about all kinds of pop music (he recorded a death metal album a couple years back), and this is his way of introducing an album that’s an amalgam of folk, country, bluegrass, and rock, or b) he wanted to lord it over Rawlings that he was right. (Maybe Dave welched on the bet?)

The last sound you hear:

An echoing electric guitar grace note fading out at the end of Sweet Lil Gal (23^rd/1^st), that fits the song and the album so well: quiet, brooding, lovely, with a touch of menace.

Track by Track:

The intro leads into To Be Young (Is to Be Sad, Is to Be High), an up-tempo bar-room floor stomping rocker of a track featuring an electric lead guitar that rings bells like Johnny B. Goode. The song brings a youthful, life on the road exuberance to the album, almost like Adams is on his way up, just moving to the big city or just beginning a new relationship with a girl, at the same time acknowledging the sadness ahead with the refrain, “Oh one day when you’re looking back/You were young and man, you were sad.”

The next track is the lovely My Winding Wheel, featuring a slightly up tempo acoustic guitar backed with understated electric guitar and organ. The song seems to address a girlfriend, or at least a love interest, a girl he defies to “Buy a pretty dress/Wear it out tonight/For all the boys you think could outdo me.” The alternative is for her to stay with him and be his winding wheel (the part of a watch that keeps it ticking). If you didn’t get the metaphor, don’t feel bad: I had to look it up, and legend has it that the first time Adams met Bob Dylan, Dylan asked him, “What the fuck is a winding wheel?”

Winding Wheel descends into Amy, a finger-picked acoustic song with deeply depressing lyrics using burial imagery (“Oh, I love you, oh/When you laid me down into your beautiful garden/Flowers and the love in my arms/It’s God playing evil tricks on me”) before telling a lost love: “Oh, I love you, Amy/Do you still love me?”

The next track is the unparalleled Oh My Sweet Carolina. It’s the tale of a wanderer who finds himself lost in the big city, feeling homesick (Adams is from the small town of Jacksonville, North Carolina) and wondering where things went wrong. Lending gravitas, and a beautiful background vocal, to the song is country icon Emmylou Harris, who Adams met while doing a tribute for her former partner, Gram Parsons. Her presence on the album is an almost too perfect nod to Adams’ place as the modern day Parsons (both as country rock genius and self-destructive drug addict).

The next track is the threatening Bartering Lines. The song is ominous all the way through, from the dark acoustic guitar lick, to the banjo complement, to the opening verse: “Hold me up, hold me down/Leave me in the withering pines/Steal my love, steal my kisses/Take ‘em to the bartering lines,” which recalls the classic murder ballad Where Did You Sleep Last Night (which of course Nirvana covered. And the background vocal provided by Gillian Welch is haunting (won’t be the last time I use that word in this piece).

We go from a threat to a sob with the next song, Call Me on Your Way Back Home, which Adams has called a song “to slit your wrists” to. He’s not kidding. A fingerpicked acoustic backs Adams plaintively wondering, “Oh baby, why/Did I treat you like I did?” and telling another lost love, “I just wanna die without you/Honey, I ain’t nothing new.” The song fades out with a heartrending harmonica solo—for some reason, no instrument evokes pain like a harmonica.

Things perk up a bit with Damn, Sam (I Love a Woman That Rains). With lyrics like “As a man I ain’t never been much for sunny days,” it’s not exactly a happy tune, but it’s whimsical in its sadness. It’s hard to love a woman that rains, but we’ve all done it, and loved doing it, at least a little.

Next is perhaps Adams’s most well known song, Come Pick Me Up, about that bitch of a girlfriend who tears apart your life but you still can’t get enough of her. Bonus points for this song because Mary-Louise Parker, uh, loves it.

Adams takes it down a notch with the next two songs. To Be the One, a harmonica and acoustic number featuring an Icarus image (anyone who’s woken up lovelorn and hungover knows the feeling of flying too close to the sun with wings made of wax) and features one of my favorite lyrics on the album “I don’t know which is worse/To wake up and see the sun/Or to be the one/That’s gone?” The self-explanatorily titled Why Do They Leave? follows in a similar vein.

The paces ramps back up with Shakedown on 9^th Street, a blustery electric number about a crew looking for a street fight, ending with Lucy (voiced in the background by Gillian Welch) catching “one in the chest.” It’s a fun, high-energy track, but it feels a little out of place surrounded by all these other mournful, quiet tunes.

The final three songs on the album descend slowly. Don’t Ask for the Water, another acoustic, almost spoken word piece that fits with To Be The One and Damn Sam, with lyrics like “Don’t ask her for the water/cause she’ll teach you to cry,” is followed by In My Time of Need, a fingerpicked acoustic number about the struggles and comforts of a rural southern marriage. The song might be a bit too self-consciously old-timey for some, but I don’t care: It’s beautiful, and the sentiment of lyrics like “I will comfort you, when my days are through/And I’ll let your smile just off and carry me” still feels genuine to me, even if it seemed corny when I typed it out just now.

The album closes with the aforementioned Sweet Lil Gal (23^rd/1^st), a song that I can only describe as haunting (I just used it twice!) and is mostly made up of echoing vocals, with a smattering of piano and the occasional electric guitar lick backing lyrics like “When I’m lonely, she makes me feel nice/Steals my shirt, makes me hurt.” It’s a song for the morning after you tied one on, still feeling fucked up about a girl you lost, wanting nothing more than to die but not knowing quite how to do it. A perfect closing track for the album.

The signature track:

The album is chock-full of great songs, and Come Pick Me Up is the most famous, but most hardcore Adams fans will tell you the signature is Oh My Sweet Carolina. If you listen to the recordings from Live After Deaf, Adams’ collection of live recordings from his 2011 European tour, it’s consistently the song that gets the loudest audience applause. Plus, it’s Nick Hornby’s favorite song. I mean, that guy wrote High Fidelity!

The signature lyric:

The signature lyric comes from the final verse of the signature song: “Up here in the city/Feels like things are closing in/Sunset’s just my light bulb burning out/I miss Kentucky, and I miss my family/All the sweetest winds they blow across the south.” Especially when Emmylou comes in on the “I miss Kentucky” line. Gorgeous.

The essence of the album:

This is probably the single album I’ve listened to the most in the last two or three years, a time that saw my musical taste shift somewhat, away from electric guitar driven hard rock and toward acoustic alt-country and folk. This happened at least in part because I think I’m starting to, as they say, feel my oats (I turned thirty during this period), but also because I started playing guitar in a bunch of folk- and bluegrass-oriented jams during this time. Adams is one of the few young (at least when he recorded this) contemporary artists that can fit in this tradition while also writing narrative songs that can hang with those of Bob Dylan (yeah, I said it) or Townes Van Zandt.

So, I love the spare style of the music, and the heartbroken (see what I did there?) lyrics perfectly fit the period of my life when this album went into heavy rotation, a time when I failed in my first shot at living in New York as an adult (obviously, like Adams, I came back) and also a time in which I broke up with a girl I’d been very much in love with and then saw her die from a chronic illness a few months later. Most of my favorite songs are sad ones, because when you’re sad, listening to a sad song makes you feel like you’re not alone in your pain (I think I stole this from David James Duncan, though damned if I remember where he wrote it). Heartbreaker certainly functions that way for me. It’s a truly great album, and a truly great desert island album.

Find all the Desert Island Albums here.