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The True Story Behind Regina Spektor's Lost Debut Album, 11:11

Regina Spektor’s debut CD was a record of legend. Twenty years later, it’s available on streaming for the very first time. This is the story of how it happened.

by Caitlin Wolper

It was 2001 in the Bronx, and Regina Spektor was surrounded by boxes. She had just ordered 1,000 CDs of her debut record, 11:11, and consequently filled her parents’ apartment with copies. But what was at first exciting had become a catch-22: she needed to sell CDs (and recoup her hard-earned $1,000 investment), but she felt the album no longer represented her music.

Although Spektor created 11:11 as a student in SUNY Purchase College’s studio composition program, some of its earliest songs were written when she was just 16. By the time she was actively playing gigs — and the album was completed — she was 20.

“When you're very young, and you've sort of moved on from something, a stage, you feel it so acutely, and it translates into embarrassment,” Spektor says. Even as she sold copies of 11:11 after shows, she felt sheepish: They’d wanted a CD after hearing her play newer work, and the CD didn’t sound like that. But she was broke, too, and needed to sell them either way.

In those early days, she played open mics in lower Manhattan at now-closed spots like The Living Room and Sidewalk Cafe, often very early (before the crowds) or very late (when everyone had gone home). Those were the slots you got as a small-time musician. She couldn’t book her own show, in part because “you were supposed to be able to bring a certain amount of people and have an audience to get a show… [but] you couldn't have an audience without a show.”

Her first real show was actually in Switzerland. A couple who’d attended an open mic in New York took a copy of 11:11 home and showed it to their friend; that friend later reached out and asked for Spektor’s fee. (Spektor calculated the cost of her plane ticket and asked for a bit less, figuring she’d spot the rest; the booker then bought her ticket and paid the fee too.) Returning to New York — where things tended to be a little less friendly — Spektor had more faith in her career. She was writing songs at a furious pace, and rapidly putting 11:11 in the rearview, but the single copy she’d shoved in her bag had helped her book that first gig.

Regina Spektor opening for The Strokes in 2003.Don Murray/Getty Images Entertainment/Getty Images

At the time, Spektor couldn’t have known 11:11 would become a record of legend: As her following grew, fans looked for the CDs that had either disappeared to the backs of collections or were aggressively marked up on Craigslist. Now, with the musician set to re-release 11:11 on Aug. 26 — over 20 years after those first thousand copies were printed — the album will be available on streaming, and in a special vinyl box set, for the very first time.

“At that time of [writing] 11:11, I was really living in a bubble,” Spektor says. Over the phone, her voice is tinged with wonder. “I wrote those songs; the most I could maybe do is play them in a class to a bunch of other music school kids.”

Purchase was the perfect incubator for her work — a school full of artsy kids hyperfocused on their chosen disciplines, and all for the sake of art itself. Former classmate Richie Castellano, who produced 11:11, said Spektor was a clear standout from the beginning with her “lyrical maturity,” use of multiple languages and sounds, and sincere vocals.

“Regina was very quiet, and one day she sat at the piano for [composition] class and she played the song ‘Braille,’ and all of our jaws hit the floor. I just remember, personally, I melted in my chair when she did that: it was obvious that we were hearing something very unique and special,” says Castellano, who currently plays in the rock band Blue Öyster Cult.

He adds that “it was not just the song, which is brilliant. It was the whole thing. It was the voice, and the fact that she was playing piano so beautifully. And she obviously had some kind of classical chops … it was rare to see someone who could write a song that great, play piano perfectly, and sing like that.”

Soon after, she asked him to work with her on recording a demo (which quickly became a full record, thanks to her steadfast work ethic).

“She was just working so hard, writing, writing, writing, writing. And also it was amazing because you just get one fantastic song after the next,” he laughs. “I'd look at her and say, ‘Who are you? What planet are you from?’ Some people can struggle their entire lives and not get one of those, one song like a Regina song.”

The pool Spektor pulled from was more often classical or a bit older, Mozart or The Beatles. As an immigrant from Soviet-era Russia, Spektor was far more accustomed to pirated music and mixtapes, so she says she had little concept of records as a unit. And she often didn’t know the musicians her friends cited: Jeff Buckley, Tom Waits, Nina Simone. Students burned her CDs, and she became enamored with blues and jazz. In the studio, classmate Chris Kuffner joined her and Castellano to play bass; Castellano says, “she really liked the sound of the upright bass and she thought it gave a little more heft to what she was doing.”

She was adamant about recording songs in a single take. “I was like, ‘The only real music is like when it's done in one take and when you don't edit anything, and you have to just like perform it and it has to have that spirit to it; it has to be the magic take,’” Spektor says.

Castellano says her eye for authenticity gave songs “that experience of hearing what it would be like to sit with her — basically the experience that I had the first time I heard her, where she sits down and she's at the piano and she's telling you a story. And she's connecting with you.”

Spektor and Castellano recorded a handful of songs before she went to study abroad in London. When she returned, he says, she “was more experimental with the production side.” Songs like the piano-led “Buildings” made way for the rhythmic and ramshackle “Pavlov’s Daughter.”

It was classmate Jack Dishel — whom Spektor married in 2011 — who recommended a company that could make her 1,000 CDs for $1,000. After all, she needed something to hand out when she played live.

The cover of Regina Spektor’s 11:11.Regina Spektor

Joe Mendelson had one foot out the door. A minority owner of The Living Room, a music venue on the Lower East Side, he usually didn’t check out the early shows — they were for newbies, the acts that didn’t draw a crowd.

That night, Spektor sat at the piano alongside a bassist. It was a 6 or 7 p.m. show, and the audience comprised two older people: her parents, he later learned. But as Mendelson left, he “was literally pulled back into the room.” A 20-year-old Spektor had begun the a cappella number “I Want To Sing.”

“I'm halfway out the door and within five seconds, I was like, ‘You know what, I need to come back in,’” Mendelson recalls. He gets choked up as he recollects — they first met after that show, and have been friends for 20 years.

“She was drawing on classical music, she was drawing on jazz music, she was trying on experimental music. She was doing things that literally just nobody was doing. She played entire songs with her left hand only, which comes from an old classical tradition,” Mendelson says. “She was singing in multiple languages: singing in Russian, singing in French, singing in English, making up sounds with her voice, banging on a chair with a drumstick while playing the piano with her other hand. It was just nuts. She was just miles ahead.”

Mendelson later produced her second self-released record, Songs, released in 2002 on CDs. He says it wasn’t long before fans, scouts, and producers were turning up at her shows. He was simultaneously “telling everyone I knew, ‘You’ve got to see this girl, she is not just another singer-songwriter.’”

“Something about all those songs is very, very, very just me, but then other things, I could just see myself searching and trying, and I did not discover certain things.”

She was also playing Sidewalk Cafe, where musician Lach was booking acts week-round as well as running Monday’s Antihoot, a weekly antifolk show that often garnered as many as 80 signups. Spektor, Lach says, came up in the show, and frequently brought new work. He recalls the community as warm, and interested in heart over anything; Lach would hold up appreciative signs during shows, like one for a “cool rhyme.”

Amid all the other players, he recalls her glottal stop; “Chemo Limo” and, of course, “Samson”; and when she hit a stool with a drumstick as she played piano one-handed. That song, “Poor Little Rich Boy,” was on her first major-label record, Soviet Kitsch.

She signed to Warner Brothers’ Sire Records in 2004 with a self-recorded Soviet Kitsch in hand. But when they offered to re-release 11:11 as part of the deal, she refused. “My biggest fear was that somebody would go to check me out and they would go listen to 11:11 and they'd be like, ‘Oh, she makes this kind of music,’” Spektor says. “I was like, ‘No, I have to just bury those deep in the dungeon, and, maybe when I'm an old lady [I’ll share them].’”

“I thought [her early work] was great, but I think she's just being a careful artist and wants to be in charge of the curation of her work, which is completely understandable,” Lach says.

The last of the CDs were sold or given away or kept, but as Spektor gained popularity, they became a commodity: Reddit users have sought it; physical copies sold for a median of $250 on Discogs; and Castellano wrote in his own FAQ that he doesn’t have any extra copies, so don’t ask.

11:11 had never been available for streaming, and was kept alive mostly by CD rips people posted to YouTube and the forum posters who kept looking for it.

“The thing is, because of the internet — this is the wonderful sort of thing about the internet, and why it makes you get over your ego and your ideas and agendas,” Spektor says, “those little sneaky records kept finding their way.”

Regina Spektor performing at Cyndi Lauper’s 8th Annual 'Home For The Holidays' Benefit Concert in 2018.Kevin Mazur/Getty Images Entertainment/Getty Images

Twenty years later, in 2021, Dishel told Spektor she should do something for 11:11’s anniversary. Her dad unearthed old recordings, and her mom old fliers. She shuddered her way listening through her earliest work, but, slowly, came to it with kindness.

“Something about all those songs is very, very, very just me,” Spektor says, “but then other things, I could just see myself searching and trying, and I did not discover certain things.”

Looking back, especially at the old videos her father (who recently passed away) took quite religiously, was jarring; but as she rewatched, she gave herself grace. She heard “familiar negative things, but there was also a counterpoint of positivity that surprised me,” writes Spektor in new liner notes for the re-release of 11:11. She writes that it was “healing” to realize that this past girl she’d cringed at had indeed worked very hard.

The 11:11 re-release is accompanied by Papa’s Bootlegs, a double LP of her father’s recordings of early shows. She liked the idea of sharing her earliest album alongside the sort of room it would be set in: “all those clinking glasses; what it felt like to play with people sometimes talking or drinking or eating.”

In the time since 11:11, Spektor has self-released Songs as well as six studio albums, and written music for shows like Weeds and Orange is the New Black; she’s played at the Obama White House; and she had a day named after her in the Bronx. 11:11, at its core, is the entry into all Spektor continues to show: deft, unique vocals; canny storytelling; impressionistic lyrics; and a gracious eye for the grand and small.

“She's inviting you, the listener, to play in her sandbox, or come into my playroom, and inside my playground, it's like Willy Wonka's chocolate factory: It's the most amazing playroom you've ever seen. It's got windup toys from the old country; it's got newfangled machines from steampunk. It's got 10 different kinds of pianos and a glockenspiel,” Mendelson says. “It's like, ‘Come into my music playroom and play with me.’ There's nothing ever in her music that pushes the listener away.”

Regina Spektor’s 11:11 anniversary box set is out now.