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Four years before her fourth album, 2006’s Begin to Hope, made Regina Spektor one of the brightest stars of the ‘00s indie boom, the Russia-born American singer-songwriter was just another starving artist traipsing around New York City, playing free gigs and selling CD-Rs out of her backpack. Flashy newcomers such as The Strokes and Yeah Yeah Yeahs were bringing national attention to the exploding downtown Manhattan scene in the early ’00s, but Spektor’s syllable-stuffed piano songs were a far cry from the sneering rock that major labels were looking to sign as they scoured the streets for new talent.

Spektor’s 2002 set Songs, her second self-released effort, was culled from 40-some songs she recorded at a friend’s studio on Christmas, simply so she wouldn’t forget them. Twelve of those (including “Samson” and “Ne Me Quitte Pas,” which she later re-recorded for Begin to Hope and 2011’s What We Saw From the Cheap Seats, respectively) became Songs, which she sold for $10 after each gig – sometimes netting enough profit to splurge on something crazy, like a modest dinner.

When her 2003 major-label debut Soviet Kitsch — and, more importantly, Begin to Hope’s breakout hit “Fidelity” (a Billboard Hot 100 entry that appeared in a laundry list of TV shows and movies) — made Regina Spektor a national name, Songs faded into the background. It’s a shame, since Songs is something of a lost masterpiece: the work of an idiosyncratic talent bursting with ideas, pithy observations, humor and pathos about the overwhelming yet inspiring minutiae of life. (If Spektor were a character in The Great Gatsby, she would probably agree with Nick Carraway when he said, “I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life.”)

But fortunately for fans, that’s about to change. On Nov. 29, Songs will be officially released on Warner Music – newly mastered by the legendary Bob Ludwig, no less, who came out of retirement to help Songs sing. In honor of its first commercial release and 22nd anniversary, Spektor will perform the album in full (plus more) at Brooklyn’s Warsaw on Dec. 9-10.

Here, Spektor talks to Billboard about those lean but creatively fruitful days selling CD-Rs out of a backpack, getting Ludwig to briefly come out of retirement to do her a solid, and how a few generous concertgoers helped her stay motivated to keep making music,

Songs is finally officially coming out 22 years after you first self-released it – and I’m thrilled you’re playing Warsaw, which is one of my favorite venues, to celebrate it.

It’s going to be fun to visit these songs as myself now and see what it feels like. Also, it’s fun to play songs people want to hear – songs they have a connection with — so I’m excited to play the shows. Obviously, people are coming to hear that record, and the record is not long enough to be a full show.

What’s it gonna feel like to play Songs in its entirety? I don’t even know, because the songs on the record were picked from whatever 40 songs I recorded that year at my friend’s studio. And the studio was not even a real studio, it was his little post-production studio — it was just his little upright piano in the corner. Nobody works on Christmas, so that’s when we would record these sessions. I think the first title of the record — we were joking around — I was like, “We should just call it Two Jews on Christmas.” [Laughs.]

It’s going to be so interesting to even see what it feels like to play the songs in that order, because I’ve never started a show with “Samson.” For many years now, I finished shows with “Samson” — that’s going to be so weird. The version of “Samson” that’s on Songs is so much slower than the one that I recorded properly for Begin to Hope –– or whatever “properly” is, you know — and so I’m going to have to tune to that version and play it how it is on the record. I’m going to stay as true to the record as I can, because I think that’s gonna be fun for me and the audience.

Also, I was joking around with somebody on my team when we were mastering it, I was like, “Why did I write so many words? Why did I write so many chords? Why did I write so many notes?” There’s just so much work in there. I’m like, “Damn it, girl, you could have been a little bit lazier! Give Future Regina a break!”

So you recorded these songs on Christmas – was the intention to have some demos to shop around?

We did we did two of these. We did it one year, and then we did it the next year. [This is me and] my friend Joe Mendelson, who was part owner of the old Living Room on Stanton and Allen. I had two homes: one was SideWalk Cafe and one was the Living Room. They had totally different vibes and I would play both of them and I loved both of them for different reasons. But both of them shared this thing where you could go and hear somebody for free. It was really a mystery, you were sort of rolling the dice.

And in that time, I was passionate about a bunch of things, but some of my passion was coming out of certain fears. I had this terrible fear of how boring it is to just have one instrument and listen to a person sing over just one instrument: “Who could ever deal with an hour of music on one instrument?” So I tried really hard to be as diverse with my accompaniment as I possibly could. If I had a really arpeggiated song that I wrote, or it was really watery with pedal, then the next one had to be really staccato. I was just trying to create this world where I wouldn’t have to play a song next to another song that sounded the same or similar. So that was kind of an obsession.

And then I also had this other misunderstanding, I guess, that if you were playing a show again in a venue, you had to have new songs. You couldn’t just play the same songs that you had played. And because my parents were kind enough to say, “You could live at home, and you can stop pretending that you’ll ever earn enough money from your stupid day job to pay rent. Let’s just all stop pretending,” I all of a sudden had this free time, and I was just obsessed with writing songs. I was writing so, so much.

And Joe mentioned something about some song from three shows ago, and I couldn’t understand what he was talking about. I said to him, “Oh, my God, I think I remember vaguely, but I don’t remember the song, and I don’t know it anymore.” And this thing started happening where I started forgetting songs. And it was a terrible, terrible feeling to be forgetting things that you care about. So he said, “Let’s just make a standing date, and that you will write down the names of all your songs and try and practice them throughout the year — and on Christmas of every year, you’ll just come in and we’ll record all of it.”

So it didn’t come through this need of trying to shop anything or demo anything. I didn’t even think of these things as anything that you could do that with. I was under the impression that other than downtown people, who would want this anyway?

When you were selling these at your live shows back then, how much would they go for? And who was buying them?

First of all, I ended up giving a lot away. You just trade with fellow musicians out of your respective backpacks. But if I was lucky, I could sell a few of them, anywhere from one or two to three at a certain point, and I would sell them for 10 bucks. And it really made a huge difference in my life. I played this show in Hoboken, it’ll forever stay with me. My mom drove me and there was this young guy there. I guess he had seen me before and he wanted to buy a CD. I said it was $10 and then he gave me $20 and he wouldn’t take the money back. He wouldn’t take change back, and he said, “No, I want you to have this.”

And — I’m like, gonna start crying — but this thing would happen sometimes where you’d go to collect your tips, and then there would be a really large [one], somebody would have put in like 20 bucks or 40 bucks. It was like this encouragement or vote of confidence or support. It would be so much more than even just the financial. It would be like, “I went through something with you, and I want you to have this money so that you can make more of what you’re doing.”

Obviously, my parents supported me more than anybody, because there was shelter and food and laundry. But if I sold three CDs, now I could look at the menu and order something for dinner at this cafe that I played. Now I can afford to go into the city for another three nights in a row to play open mics, and take my backpack and hope that maybe I’ll sell another two. You’re going from tiny payday to tiny payday.

How were you thinking about your future at the time? Were you hoping to make it to a major label, or were you just feeling, “Well, this is my life, playing music at these downtown venues and selling CDs out of a backpack”?

Well, it’s a really good question, because I think actually at that time — I very much feared all big labels. Even when I started talking to them all, I was still very much terrified. One of the people who signed me [to Sire], Goldie, Michael Goldstone, he basically, at a certain point was like, “Why are you talking me out of signing you?” [laughs] And I was like, “Because I won’t do this, and I’m not going to do that.” I just had heard all of the horror stories, and I was very fiercely protective. I knew in my mind that the most important things were the songs to have that chance and time to develop without being under scrutiny and without everybody’s opinion in there.

When I think about musicians and artists that are starting now — forget about labels, everybody’s opinions are there all the time because of social media. You can’t get away from people’s opinions and thoughts and ideas for you and about you. That’s a hard path, because there’s something so wonderful about just being so underground and free and making your own decisions based on a feeling rather than a comment. But that being said, I think that we have to be careful. Much like when you read A Moveable Feast, all of a sudden you want to move to Paris and starve with everybody. There is definitely a magic and a nostalgia that I have — I loved that time, I was very lit up, and it was really, really creative.

And then there was another part of it that was really, really hard; it oftentimes felt endless and exhausting and confusing. Growing up is not easy for anybody, and it was part of growing up and figuring out how to be your own person in the world. And when your world is New York City, it’s pretty full-on — it doesn’t take it easy on you. I mean, just living in the Bronx and playing downtown. I lived on the subway. I could easily spend four to five hours a day on the subway, traveling to and from places, because if I couldn’t afford to eat in Manhattan, I would come back to the Bronx and then come back to Manhattan [to play again]. The reality of trying to be an artist in the world that doesn’t really support art. But the people who bought those records allowed me to live.

When you started revisiting this project, what was it like? Did it feel familiar, or like the work of a totally different person?

There was the very first re-finding of it, which was the CD-Rs that I sold at shows. They had so much interference and little things on them. I hadn’t listened to it in, whatever, 20 years and I was like, “Oh no, I can’t just put this out like this.” My friend’s studio actually was right near Times Square, so there’s a lot of interference. It wasn’t meant for live recording, really. But we were able to find an old hard drive that had original files on it. And through that, Bob Ludwig — who is mastering extraordinaire, and I’ve had the pleasure of being friends with him, and he’s mastered everything from Begin to Hope and on, and then he retired — I reached out to him. And he basically came out of retirement to help me.

[After that] I could listen to these songs instead of just obsessing with every little interference. Once that layer was gone, it’s kind of like when you look at baby pictures of yourself, or have memories of yourself at six or eight or 12. You’re not exactly that person, but in a way, you could be right there. That person is still inside you. That person is just there, but another layer grew over it, like the center of the onion.

I completely understand her [when I listen to Songs]. Some things, you’re like, “Wow, I’m really proud of you for that” or “I’m really amazed at you for that.” Versus sometimes it’s with an eye roll of like, “Oh my God, now I have to say this thing? Why did you write that?” It’s mixed. Same as Future Regina is going to be doing an eye roll about something I’m doing now, and then she’s gonna hug me into the past for something I’m doing now. We don’t know what those things are. But I absolutely recognize the person that wrote [Songs].