It would be remiss of me not to point out at the beginning of this feature that ‘Heartbreaker’, the debut solo outing from Ryan Adams, is in my list of top ten favourite albums of all time - and has been, since it was released in September 2000.

I was 21, stuck in a small town, getting over a failed relationship, and trying to work out what the hell to do with my life. Into this bleak and forlorn landscape arrived a record that, from first listen, seemed to soothe my pain - this voice so clearly hurt and vulnerable was echoing my misery, and became my confidant and comforter when I needed it most. Fast-forward 16 years to this week, as Ryan prepares to release ‘Heartbreaker Deluxe’, an extensive reissue featuring previously unreleased outtakes and demos, and I have the pleasure of revisiting and reinvesting in the record’s original 15 songs in the name of research, before confronting the author to dissect their origins.

It’s still an affecting experience; Ryan is sweet and articulate despite bearing his soul in hauntingly poignant admissions of sorrow, and the largely acoustic folk palette stands as one of the most authentic and timeless communiqués from the more earnest pedal steel-drenched bands lumped together and labeled by the media as alt.country at the turn of the century. Times may have changed - I’m 37, living in the big city, very happily married with a beautiful baby girl - but ‘Heartbreaker’ can still cut deep.

Why?

Because it’s a sincere manifestation of a chillingly comparable reality. As Ryan reveals in our 90-minute conversation, when he made ‘Heartbreaker’ he was 25, stuck in a small town, getting over a failed relationship, and trying to work out what the hell to do with his life.-

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You don’t have to have suffered the same pitiful circumstances to enjoy ‘Heartbreaker’, but in unconsciously identifying with the record I created an abiding bond that brings me back to its consolatory grip when moments of reflection are required.

In their original review, Pitchfork called ‘Heartbreaker’ a “drinker’s album”, and, man, are there times when you want to drown in it. It’s not entirely harrowing - first song ‘To Be Young (Is To Be Sad, Is To Be High)’ bounces in like a boisterous cut from ‘Blonde On Blonde’, suggesting a streak of alacrity may run through the subsequent 14 songs, though really it’s the first, refreshing shot on a long night of drinking - but it’s when Ryan is at his most exposed that the album’s depth truly reveals itself.

For example, in the intimate picking of ‘AMY’ - a song bravely (or desperately, depending on the way you look at it) named after the aforementioned girl who abandoned him - when he asks, “Do you still love me?” Ryan immediately unmasks himself as a man dreaming of the past and crushed by hope, a theme exhumed later in ‘Why Do They Leave’. In ‘My Winding Wheel’, he seems to be appealing for someone to take a leap of faith in his romance, while the compelling ‘Come Pick Me Up’ finds him longing for the company of a girl that’s clearly intent on doing him wrong. ‘Oh My Sweet Carolina’ alludes to a yearning for his native state - perhaps his sanctuary after recently leaving home in New York (although the truth, as we’ll find out, is somewhat to the contrary) - but by ‘Don’t Ask For The Water’, I hear him pining for the memory-filled streets of Manhattan.

In the years since ‘Heartbreaker’, Ryan has explored and adventured with an inquisitive musical muse that’s touched on his beloved punk and metal and deeper country, and while he’s remained an existential prober throughout, this record, I think, is matchless in capturing the dejection of an angry and confused young man. Yes, 2004’s ‘Love Is Hell’ is somewhat darker - Ryan sounding even more damaged than on ‘Heartbreaker’ - and while subsequent albums have dealt with the deaths of friends and family, and the dissolution of later relationships, ‘Heartbreaker’ feels the most complete and endearing in its full disclosure.

We find Ryan at home in LA, looking back at the album that marked his departure from previous band, Whiskeytown, and his arrival as the guitar-picking poster boy for fucked-up millenials. Given the record’s distressing provenance, I was naturally expecting him to be reticent to discuss his frame of mind at that time - as it turned out, only the power of the blazing California sun and its ability to overheat and restart Ryan’s phone could stop him talking.

This, then, is the inside story of a perfectly titled album - bruised, blunt and brilliant.

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What is your relationship now with ‘Heartbreaker’ and the songs on it? When you hear it, are you still connected to it, or have you moved on completely?

Well, here’s one good thing to say: I don’t believe in revisionism for me. Because when I experience ‘Heartbreaker’, when I listen to it, I’m hearing me; I’m hearing the person who I am now, but I’m hearing me at a much younger age, at a time when I hadn’t maybe completely learned to be myself all the way. Or maybe I can hear me sort of experiencing my own lessons. Like, ‘Heartbreaker’ for me was always a really good record, and there were moments on it that were so special and what I made was very important. I had a lot on my mind, and I was also leaving the confines of being in a band and a record deal or a situation that had made it where I couldn’t really record for a while. It took a minute to sort all that stuff out.

If you remember at that time, it was the time I believe when Seagram bought like Geffen and all those other labels, and everyone was like, ‘The end is coming!’ Whiskeytown were still on a subsidiary of Geffen - Outpost Records - so there was a long time building up to making ‘Heartbreaker’ where I couldn’t really legally or contractually do anything, and I didn’t have a manager, and I just didn’t know what to do. I also had moved away from New York City for a brief amount of time because I was broke and I couldn’t afford to live there. And my girlfriend had moved - she had moved away… It was a crazy time for me, you know?

So, the things I remember about the record are different than someone if they listened to it and it marks a time and place for them. I just remember sleeping in this huge, empty house in Nashville, off of Gallatin Road, and my manager at the time, who I’d just gotten, basically rented the house for me so I would have somewhere to live, but I didn’t have a car so I couldn’t really go anywhere, and I didn’t have any furniture, so I only had like the clothes on my back and a suitcase of clothes, and that was it. There was one lamp that somebody had left in the house that didn’t have a shade. I would just leave that on when I came home, and then I would fall asleep at night on the floor of this one bedroom with just my jacket curled up as a pillow.

And then, later on, I found out that the house was infested by brown recluse spiders, which are like actually deadly. (Laughs) They can kill you!

Holy shit.

Yeah, you can get atrophy from them and all kinds of stuff. People warn you against brown recluses. You can look them up, but it’s a terrible thing. And when I went into the basement of the house - which I’d thought, ‘Oh, I could put a four-track down there’ - the whole basement and all the downstairs had become totally infested with spiders. And somehow I never got bitten. So I just recorded every day and went back and slept in this house.

Putting your life on the line for your art!

Yeah, it intensified the whole feeling of like, ‘Whoah, I’m no longer…’ There’s a song on the record called ‘AMY’ and I had been with someone named Amy for a long time including in New York, and in this environment that was extremely different, and now all of a sudden I’m in Nashville; it’s very quiet and weird, I don’t know anyone really… But yeah, it was extremely bizarre. When I listen to these tracks…I just listen to me and I go, ‘I hear this 20-something person and I hear the worry in my voice.’ I’m not really listening to what I’m saying, I’m more going like, ‘Wow, I can really tell that I’m broke and I’m scared and I don’t know what’s going on.’

I mean, I was ready to get a job at the time. That was my plan: to go back to part-time construction work and just tour on the side when I could. Everyone around me at that time would basically say, ‘Your career is over. Your one shot at being anyone is over because of the commercial failure of Whiskeytown.’ So I was just there kinda going, ‘Okay, well at least I’m in Nashville, so I’ll be able to gig a little bit and do what I love when I get off work.’ That was all I was really thinking about.

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You mentioned almost in passing the fact that you’d broken up with your long-term girlfriend just prior to ‘Heartbreaker’. That’s quite significant given that it’s a theme running through the entire album. You once said that the album included “a lot of things I needed to say”. Was making the record a cathartic process?

I mean, yeah. I mean, one thing I can tell is that I was listening to a lot of Bob Dylan, and then the other thing was that I can tell that I was looking for my own voice. I was still looking for my own voice inside of the touchstones that had been there with me or had followed me around. And even in this weirdness, it was nice because that record sort of started to veer away from my weird version of country music. Because, you know, I had always thought about country music as an abstract thing; when I played it, I always played it from the perspective of someone that just played drums in a punk rock band, or played in post-punk Hüsker Dü-sounding bands.

So the idea that somehow I played that music in Whiskeytown, or even up to ‘Heartbreaker’, it wasn’t meant to be ironic. I wasn’t doing it and saying, ‘Ha ha ha, I’m playing this kind of music that I don’t believe in,’ but I always felt like - to me - that there was a playfulness to being in that style, but I guess if someone doesn’t know me they wouldn’t read it that way - they would just read it as how I was going about it. Because they wouldn’t know like, ‘Oh, well he’s not that kind of a person.’ In fact, to this day I don’t think that people understand that I basically listen to ’80s hardcore records and metal. I don’t really listen to country music or a lot of folk music. I mean, I will listen to some of it sometimes, but it’s not… It’s what I write.

Who I am as a writer doesn’t have to be defined by what I read. And I always really don’t understand that. For me, I always think how close-minded it would be if my whole thing, like all that I ever listened to and all that I enjoyed, was folk music and country music, and then that’s all that I did. It would seem very weird and repetitive to me.

Were they easy songs to write? You once said they felt “instinctive”…

Yeah, but they were my first real complete songs. I don’t really think that I was writing complete songs until the third Whiskeytown record, which was basically like a solo record because there wasn’t much of a band left, but that was the first time that I started writing things like ‘The Ballad Of Carol Lynn’ or ‘My Hometown’ - these weird kind of ruminations on what I really was. And also, I had changed from being just like a very young lush - like a drinking kind of idiot; I just wanted to listen to records and drink before that time, and I think some time before ‘Heartbreaker’ and into that time - because I was still quite young and writing - I think I had discovered a couple of different things, but one of them was, you know, I was like, ‘Oh wow, I have an anxiety disorder,’ so I was able to stop self-medicating, and there were times of clarity where I could just sit and finish a thought.

And then also, a lot of those songs were written in bars. I was so lonely and I would go to a bar and I would bring like a notepad in my back pocket and I would write out the lyrics. Quite a few of them were written in the couple of weeks right before I actually moved away from New York City, but they were written on a typewriter in a near-empty apartment, where I’m kind of looking at the place where I had lived and knowing I was going to say goodbye to it.

And weirdly, songs that later on would go on ‘Gold’, some of them were written at the same time. Some of the lyrics, and definitely the original version of ‘New York, New York’ was written at the same time - as was a song called ‘Dear Chicago’ that later came out, and a bunch of other things. I was already kind of stockpiling those ideas, but they weren’t ready to be on a record. And then there’s stuff on the record that I don’t connect with… There is some stuff where I listen and I go, ‘I’m trying on different hats.’

Trying to find yourself, as you said earlier.

Yeah, well, I mean, I think I was pretty close. I mean, what’s really great about ‘Heartbreaker’ is that I knew how close I was to being who I was on that record, even though stylistically, for me, I knew it was… Like, I wrote the songs to be that way. I wrote those songs knowing I would go and tour them by myself, and I wrote them by myself on acoustic guitar, and I wrote them knowing that I wanted them to be abstract.

I was reading a lot of poetry and I was listening to a lot of Big Bill Broonzy and Sleepy John Estes and Bob Dylan and Bert Jansch and it led me to really want to paint these crystal clear pictures of loss and being lost. But I still hear the man in there, like not knowing fully… What feels good to me or what was interesting to make that record is I had no idea that people were buying it to be something that magnetised them to it.

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"I firmly believed I was making a kind of like little record to go away and make a little record to sell at my shows that I was playing when I wasn’t working. I didn’t have any clue what it would do."

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I think that’s exactly what gives the album its appeal; there’s a naiveté in there. You can hear someone amid the process of finding themselves, exploring these myriad emotions they’re experiencing, and it doesn’t sound like the reactions of someone a bit older and wiser; the songs are impulsive, and there’s a lot of questions being asked to the world, and I think that innocence really shines through it warmly.

I feel like the ‘questioning the world’ thing has been a mainstay of most of my work, though - especially in the last couple of years. (Laughs) But I know what you mean; I’m questioning it definitely in a naïve way, and I think that me playing around with that style was also naïve and probably forgivable somewhat. I’m really proud that I was able to make that record and for it to be not polarizing but instead people loved it, and it seems loved by people who probably wouldn’t have otherwise really given a shit about me anyway.

I’d like to ask you about some songs and specific details from the album, starting with the opening track - the dialogue of your argument with David Rawlings regarding Morrissey (concerning the song ‘Suedehead’, and which album it appears on): who won that bet, and did they ever receive the $5?

No. I don’t believe I ever collected the cash, but I was correct. But I think that maybe Dave was correct too. He had like a cassette version of ‘Bona Drag’, and I think that maybe he had said to me after all of that that the track in question was on the crease on the fold on the back of the cassette, so he didn’t know. And I guess strangely he wasn’t that familiar with ‘Viva Hate’, not as much as the second record or the singles collection, because that’s the standout track on ‘Viva Hate’.

I guess it was his cassette copy, but the American versions of those records are different - just like The Smiths’ records, they’re sometimes slightly different than the ones that come out in the UK or even sometimes in Europe, and I think that that’s probably the same for the Morrissey records. I don’t know if he does that intentionally or what, but it definitely makes a good record collector out of me, because I try to get every one ever. (Laughs)

I love that it’s the opener; the album sounds very intimate anyway, but it’s like you’re inviting the listener in at the very beginning to join in on a private conversation. It draws you in immediately.

Yeah. That’s definitely… I think that that’s probably pretty fitting of what all those sessions were like. I mean, that’s the most social interaction I probably had at that time, if I wasn’t in a bar. I’d go to a bar and sit by myself and write, and then if I went to the studio I was just with the people I knew. But I spent most of those years pretty much alone, and so when I would see people that I admired and played music with, it was always a really good time. But I love that my solo career starts with me talking about my favourite band of all fucking time!

And a song like ‘Come Pick Me Up’, the left and right [panning]… the reason I used the electric guitar in one and banjo in the other - you can even hear it on the demo - is because I was trying to find a way to do what Johnny Marr was doing on songs like ‘Unhappy Birthday’ and things like that; I was trying to find a way to keep things really raw but have there be these beautiful arpeggiations, but then use a banjo and an electric left and right instead of a 12-string and a high-strung guitar, or the tricks that he does. I was trying to find a way to say like, ‘How could I make this more swampy?’ Like, how could I re-interpret the feelings that I get from Smiths records and the arrangements but in a way where it felt comfortable and real in the setting of my own tunes? I think that I got there.

When people listen closely on tracks like that, it’s very obvious. And what’s cool is, on the deluxe you’ll hear way more of that. In fact, we kind of muted that influence a little bit when the songs were selected and the thread made sense to us. We chose more intimate things, even in place of things that might have sounded more commercial or had done better. And, in fact, the funny thing is that when I first turned the record in - she’ll hate me telling the story, but it’s real - but when I first turned the record in - because even though I owned it, it was basically going to be a licensing situation - my manager and I were having a disagreement over whether to [go with] Rounder Records or somebody like that who was interested, but I was like, ‘No, I want to do it on Bloodshot,’ and when we handed it in, I remember Nan from Bloodshot was not thrilled with it.

She was like, ‘First of all, this record is too slow.’ Then she’s like, ‘Second of all, you can’t just have a song called ‘AMY’.’ She’s like, ‘What is that song? Is it just about your ex-girlfriend, Amy? That’s just it? You’re just going to say that?’ And I remember having this weird conversation on the phone and I was like, ‘There isn’t a negotiation. This is the record. Nothing is going to change. This is what I have to say. I don’t know what you were expecting.’

I think maybe they were expecting a much more lively and rabble-rousing kind of album, but I think maybe they were kind of nervous because of the initial investment that they were going to make to secure it, and I handed in this thing that’s kind of gloomy and dark and slow and cerebral. And I always thought that was so funny because, man (laughs), even from the very beginning I had trouble handing in a record! (Laughs)

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Wow. Had they never heard a song like ‘Sara’ by Bob Dylan?

Well, in all fairness, on Bloodshot, a lot of the bands are almost psychobilly kind of stuff, like Waco Brothers; they would sound country but they’d have electric guitars - sort of sounding like Merle Haggard was having a big drunken party but there weren’t any acoustics around or something. A lot of that kinda stuff, which was never really for me, but definitely was the stuff that I was exposed to or around during that time when I was in Whiskeytown. That was the predominant sound of bands at the time.

So everyone was trying to figure out, ‘How do we harness this kind of wild country sound and re-interpret it?’ You had bands like Uncle Tupelo, who were basically doing like a Dinosaur Jr. version of that, and then bands like The Jayhawks, who were kind of beautiful harmonies and drifting over… There were all these different flavours out there at that time, and it was still ticking, I think, when I did ‘Heartbreaker’, so it was probably a shock to hear that and go, ‘Whoa, this is really sedated.’ Besides, maybe, that song ‘To Be Young’ or whatever, it was much more mellow.

But, you know, that was my introduction to… I think that was that time of life where… You know, for me, everything I’d ever wanted was over. I’d always wanted to be in a band and not have to have a regular job, make records for a living, tour - and then, I’d obviously really enjoyed my relationship - and so, for all those thing to kind of go shit at the same time, that was the first real adult dose of going, like… I literally thought, like, ‘I just lost this person I love so much. I can’t live in New York because I can’t afford it. I can’t tour because there’s no record for me to put out and my band are broken up, and I’m broke and I have to move back,’ which I did before ‘Heartbreaker’.

I literally moved back to my hometown of Jacksonville, North Carolina, which is a fucking small, very economically depressed, not the safest place in the world to live. And I mean not the safest place because of just the police even there are crazy. It’s just a small crazy little town, and that’s where I went to go live and write this stuff, and then I went back to Raleigh, North Carolina, for two minutes, and then made my way to Nashville, where I ended up recording it and that’s where my manager lived. So, I hear that in my voice. I hear this person going, ‘Holy shit, the dream is gone.’ So there wasn’t much to celebrate. I wasn’t going to make a record where I was like, ‘Yay! All my hopes and dreams are fucking over!’ (Laughs) I didn’t really feel like celebrating any of that shit.

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Was ‘Oh My Sweet Carolina’ written while you were there? In that song you can hear some nostalgia and perhaps homesickness, but it’s countered by a sense of hopelessness and maybe loneliness.

I mean, I guess. I don’t want to change anyone’s perceptions of that song, but I’ll share as much as I can. The subtext of that song is that I want to fucking be any place but there. Because, for me, North Carolina, when I think about it, I only think of my grandmother and grandfather, and I think of the good times I had with them. When I think of that place, that’s the only thing that I could think of… Like, I instantly think about watching baseball as a kid with my grandfather, who was very ill with emphysema for almost eight years, so a lot of my childhood was spent hanging with him because he was very sick.

They gave him a very short time to live - seven months - but he ended up living seven-and-a-half years, mainly because he had said that he didn’t want to die before the Braves won the World Series. I think I even remember at the time going, ‘Papa, you’re going to live forever, because they’re never going to fucking win!’ (Laughs) At the time, anyway, they weren’t the team to go to the World Series very often, and after about seven-and-a-half years I think he gave up. (Laughs) He was like, ‘I’m out of here!’ (Laughs)

So, when I think about that song, I think about particularly that specific thing, and the love of my grandmother, which was tremendous and beautiful. But every other aspect of North Carolina for me in my childhood… My parents: I didn’t grow up around my father, he was gone, and my mother and I are not in any way close, which made me sort of an outsider to my brother and sister, so I ended up spending most of my childhood with my grandparents. So that song is kind of for them.

And then, the subtext, or the subtle irony, or the subtle dark humour, is the “what compels me to go”. It’s a joke to myself. There’s nothing ever to keep me there besides maybe my grandmother… Even though a song like ‘Sweet Carolina’ sounds nostalgic and like I want to go home or something, I listen to it and… I mean, when I play it to this day, I get this sense of resignation, or I sing it from the perspective of knowing that you really can’t go home again, and you really can’t expect to return in any kind of a pure way to something that disappointed you. And maybe that’s why ‘Heartbreaker’ is an ally for people who are feeling the same way: because I’m saying all those things for the first time aloud, and maybe it’s such a new experience I’m even surprised to hear myself say it, or I’m still saying it in that way where I’m not even really thinking about it and not processing it at all; I’m just kind of going, ‘Holy shit, this is kind of a dark world,’ you know? (Laughs)

How do you think the album actually found its audience? It didn’t really get any radio airplay, and sales at the time were just okay, but it became a cult favourite. What do you think led to people actively seeking it out?

I don’t really know. I mean, I know I went on tour. I had an acoustic guitar, I was always surprised when people showed up, I played some pretty good gigs at that time… Those were really beautiful times. For me, the ‘Heartbreaker’ tour, when it got to Europe, that was the time that I fell in love… You know, there are certain people in the United States that fall madly in love with going overseas and experiencing difficult cultures, and for me, I think by the time I got to Sweden and Norway… And really, all the time that I got to spend not just in London, but the fact that I did a lot of that tour by train, and I went to the smaller towns like Sheffield and Leicester. I wanted to do that. I didn’t want to just go over and play The Borderline and that be it; I really wanted to try to somehow go and play everywhere. I wanted to see all of the UK - I wanted to see Scotland, I wanted to go to Wales, I wanted to go to Ireland - so I kind of stayed moving. And I think that that probably helped a little bit.

I mean, more people knew about Whiskeytown. Maybe it took a minute, and then I think maybe because of what it was, I think something happened. But the first time that I ever realised that I had done something that mattered, was… I didn’t have a computer - I didn’t even have an ATM card; I didn’t even know what the fuck they were. Like, I literally kept my money in my sock. I was such a Luddite. Which is really funny. I literally didn’t know anything about anything.

But by the time that I got back from the solo tour and I got to Nashville - where I had been and had met a few people and was starting to think about playing and assembling a new band - the bass player in my band, Billy, he used to get MOJO magazine - it might have been Q or something - and he goes, ‘Ryan, you’re in this!’ I was like, ‘What?’ It was a live shot of me playing, and somebody did this review of my acoustic show somewhere, and I couldn’t believe it. I remember looking at it and I was like, ‘How did they even get that photograph?’ Like, I was so tuned out of my career or what was going on. And so, at some point - I don’t know how - it just found its way. You know, those were the days when people took chances on records, I guess. I mean, record stores were still a destination spot that I think people went to weekly, before people bought stuff on iTunes.

Well Ryan, we could probably sit here all night because I could talk about ‘Heartbreaker’ until the cows come home, but I don’t think either of us has got the time.

By the way, when do the cows come home?

Very soon, I think.

What do you think it means though, that the cows are coming home? I’ve always wondered about that expression. Like, are the cows on vacation?

I think maybe they’ve just been out to pasture, having their lunch, and need to get home for milking.

I mean, how do you get the cows to come back, because I’ve only ever seen them out in the field. I guess maybe you have to ring that fucking bell, right?

Oh no, you don’t want to start with cowbells - that’s when the jazz bass solo comes in!

I guess if you really wanted to call those cows back and didn’t feel like ringing the bells you could just play ‘Don’t Fear The Reaper’. That’d be kinda cool, to try that out sometime. See, that would be something to back to North Carolina to experiment on, but that would be the only reason. Maybe I shout write a fourth verse to ‘Oh My Sweet Carolina’ and say I will only ever come back if I can experiment with playing ‘Don’t Fear The Reaper’ to see if the cows will come home. (Laughs) Maybe this is why my current music has a different flavour than ‘Heartbreaker’, because I’m willing to put a line like that in a song now. (Laughs) It’s like, thank God for a sense of humour that only can manifest itself after something like that record. I’m really glad that we had this conversation, and it was nice to talk to you about it.

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Ryan Adams’ debut album ‘Heartbreaker’ special 180gm 4-LD/1-DVD deluxe edition box set featuring the original album remastered, demos and unreleased outtakes, plus a live DVD of unseen footage is released this Friday, May 6th, on Pax-Am Records.