JOAN WASSER: This is the first song off my first album. An album that I made because I had to, and one that I didn’t have any preconceptions about. I knew I liked what I had made and that my close people would hear it, but other than that I had no idea if anyone else would hear it and like it.

Also, I was releasing it at the age of 36. I’d already had a whole career in music as an instrumentalist, as a band member, and as an arranger, but not as a singer or a songwriter. So I really had no idea, but what I did know from my experience in the music industry was that I was going to do everything exactly the way I wanted to. And one of those things was putting this song first, which is something that maybe not many people would have done, but I felt like it set the mood of what I was doing on this record.

The song is about going to the post office to mail a letter to someone, though it was actually to mail a letter and a cassette tape of the song, which I don’t mention in the lyrics. I was mailing it to this person overseas and hoping that the song and the letter will convince them that I am the one for them. I really like the way the song describes the actions and the feelings in that moment, and then it goes into a sort of aria-type section where I’m singing “I’m real life / You’re real life / We’re real life,” before going back to the story again at the end.

I chose it for this list because I think the song was crafted in a way that I truly felt worked well for me. I think if something feels true then you know it’s right, and it seems that other people really do feel that too.

BEST FIT: I loved the twist to the story that you talked about on your Joanthology podcast, where you were saying, “I’m real life / You’re real life,” and he was like, “Er, no.”

[laughs] Yeah, I don’t remember what I said on the podcast. To be honest, I don’t ever remember much of what I say. But what he said in response was really quite profound. There’s a part in the song where I sing “So take the chance, be reckless with me,” and what he said was “But Joan, I don’t want to be reckless with you.” That was so generous, actually, and proved that he was a very decent person. I mean, there was a reason why I wanted him to be the one, even though he knew that it wasn’t right.

I totally see now that it wasn’t right, but you know how it is when you get obsessed with an idea. It was a fantasy. I created a fantasy in my mind of what it would be like, and I think we often do that with our love interests. He was more reality-based.

There's a gorgeous poetry to this song. The line “How a man, desired, feels the weight of a letter” is a Joan all-timer for me. What’s the story of how this song came together? Was it one that you had to labour over?

It was one of those fever dream-type songs where I was feeling like I just had to get it out of me and work on it every second until it was finished. At the time I was living in a place where my piano actually had its own room. By which I mean the room was the size of the upright piano and not much room for anything else. It was tiny, but it had a window that looked out on a tree that was really, really beautiful. I remember the feeling of losing time while writing this song. I could see the tree and then all of a sudden it was as though it was a different colour, and then all of a sudden I couldn’t see the tree anymore. That’s what it felt like to me, though I think the song was pretty much done in a few days, with more or less continuous work.

The success of Real Life put you in good company among the group of American artists who were first embraced by the UK and in the rest of Europe, and in your case it was quite a while before America caught up. I remember that the album wasn’t released there until about a year after it came out over here. What was that period of time like for you, being away from home so much in Europe?

It was so exciting, and so surprising too. I was touring Europe basically the whole time and was really learning how to play live without a band. In 2004, I went on tour with Rufus Wainwright and opened the shows solo, even before a lot of the songs on Real Life had been written, and that had its benefits and its troubles. I mean, first of all, no one had any idea who I was – they were all there to see Rufus – but it definitely taught me a lot. A lot of people did listen but there were also times when the whole place would just be talking throughout my set. So the fact that I was able to come back with Real Life and play my own shows, and have everyone just be silently paying attention… it was so emotional for me. It was so different, and really I just couldn’t believe it, you know?

JOAN WASSER: My dad was a really good person. I think we should honour it when parents are really good, because we hear so much about people who are terrible parents, or at least I do. I guess everybody’s doing what they can, but, you know, there are a lot of stories. Anyway, my dad was a really good father who was very supportive of me. He was quite a foil to my mum, who was great in other ways, but she could be quite harsh. She could be very judgmental and strict, whereas my father was so quiet and low-key. I don’t think anyone ever really know what was going on inside him.

My dad was a scientist, and I felt like he kind of lived in that world. Like, he truly did not judge anyone. He just didn’t have that built into his character in any way, and I wanted to thank him for that. There’s something he said that I put into the song, which was “I could never see what passing judgement on anybody else would ever do for me,” and I was like, “What the fuck dude?” because it was just so beautifully put. I wish he would have written a book.

He didn’t study Buddhism – he was an absolute atheist – but he just had things worked out in his head. People can make things very convoluted and confusing but [accepting people for who they are] is pretty simple, and I think he saw that. It was a great relief to me, to have a dad who was that way, and I really wanted to honour that. I wanted to write a song that would remind me, every time I play, it that his way was a way to be, a way that I can also be if I want.

With this song, again, I found that when I feel like I have actually captured what it is I wanted to say, it ends up really resonating with others. A lot of people have told me how much they really love this song.

BEST FIT: What is it that you love about how it turned out, musically speaking?

Well, that record, Damned Devotion, was a record that came off the back of doing a collaborative record with my friend Benjamin Lazar Davis. I had done some home recording before, but Benjamin is really all-in with that stuff and I learned so much from him. I learned how easy home recording can be, and then I just ran with it from there. So I think Damned Devotion has a different kind of feeling to it, because I’ve taken a lot of sounds that were not made from live instruments and altered them. It was a really fun exercise in sound design for me, and I just love the combination of live musicians with affected or simulated sounds, and this song has some of that on it.

The main reason I chose it, though, is really that I feel like I somehow hit the truth of what I was trying to say, not only in the lyrics but in the melodies and the arrangements.

I thought it was interesting that, unlike “Real Life” and “The Magic”, this song doesn’t appear on your Joanthology retrospective. Would you say that this song has become more important to you as the years go by?

You know, I have no idea what’s on Joanthology. I didn’t even realise that! There are so many songs on that record. I’m not sure why I didn’t put this one on there, but it’s not because I didn’t like the song.

With a collection, I feel like I always want to put all the songs that come last on my records, because those are the songs that people don’t often hear and they’re just as important. Not every song can go first, right? But, yeah, this song has always meant a lot to me. I’ve written a lot of songs about the people that I’ve lost, and I feel like this is the one that reminds me that I can continue on in life happily.

BEST FIT: Most people find it hard to choose a personal best from a brand new record where they are often very invested in every song, so it’s always interesting to see which one they go for. What’s special for you about this particular track, which is quite an unsual song for you?

JOAN WASSER: Yeah, typically I write songs starting with the music and getting some kind of chord progression going, but I’m always interested in figuring out new ways to write songs. I also love reading and writing words, so several years ago I started to take writing workshops to see if I could start songwriting with the words coming first.

Last summer, I took a workshop with the great poet Marie Howe and wrote most of the words that ended up becoming “Lemons, Limes and Orchids” through that. Then, when I was figuring out the record, I was considering what it was that it needed to have in terms of songs. I love Bob Dylan and Leonard Cohen, and I love an epic song that has a lot of verses with a lot of words and a very simple chorus, but I’d never really considered the idea that I could make a song like that myself. I just didn’t think it was in my wheelhouse, even though I love that music so, so much. This time around I just thought, ‘Let’s see what I can do here. Let’s see if I can make this happen.’

So, I went back to that piece that I wrote, reworked it a little and added a simple chorus, and it came together very quickly. The song has very simple chords because it’s really all about the words. I love different voicings in music and I love to try out putting chords together that don’t necessarily ‘make sense’ or whatever, but this song doesn’t have any of that. I had to ask myself, like, ‘Does this song stand on its own without any particularly interesting chords?’ and, at first, when I’d finished it, I really didn’t know what I thought about it. Now I love it, and I wanted to include it here because it feels like something different for me and kind of exciting.

The song is about a time in my life, before cell phones, when I would wander around on the west side of Manhattan. This was before it was developed at all so it was really deserted. I mean, any part of New York City that’s ‘deserted’ still has a lot of people in it, you know? I wasn’t doing well at the time, and it really helped me to just walk for hours and hours in a place where I knew the chances were low that I would see anyone I knew. I think these days they call it something like walking meditation but that did not exist in my vocabulary at the time. This song is really just documenting that time in my life where I was just trying to figure some stuff out and I needed to walk.

The song poses a question that you let linger without an answer: “What is more beautiful than what really happened / What truly happened there on the west side?” Can you shed some light on what inspired that?

That’s just about transformation, which is something that can happen basically anywhere if you’re open to it, and if you give it time and patience. I think that’s the hardest thing to do for me, to be patient with things and think ‘Okay, I just gotta give it some more time.’ But it will come if you just allow it, and it can happen in any space. You don’t have to be in some pristine retreat. It can happen while out walking in the filthy streets filled with lots of people who are also trying to figure things out.

I’ve only played it live a couple of times so far, but I’ve found that people have really responded to it. It’s always interesting to me when people bring their own experiences to a song and say, ‘Oh, that happened to me too,’ even though it’s often not what had happened to me. It just brings something up in them, and I feel like that, for me, is the magic of music and the magic of words. Once I put something out in the world, it’s not mine anymore, it’s the listeners’. I think we all use music in the way we need to, and the only way we can hear it is through our personal experience.

I love that the song has an almost romantic sounding title but is actually referring to discarded flowers and fruit peels in the dirty city streets. Is that an image you remember from real life?

Yeah. I mean, there's so much trash in the city. It's so funny whenever somebody comes to New York and they're like, “Wow, it's so dirty here,” because I don't ever really pay attention to that until someone points it out. I'm so used to it.

Trash is always present in New York, and it's actually something I love about this place. I observe it as part of the beautiful landscape of the city. Going to a clean city kinda makes me nervous.