Spektor turned 21 the same year she self-released 11:11, but the seriousness of adulthood never sunk its claws into her. Back then, and arguably still, she anchored her outlook with a buoyant optimism and sense of wonder. During a semester abroad in London in the then-dreary neighborhood of Tottenham, she fawned over Argos catalogs and found comfort in the area’s similarities to the Bronx. The summer prior, she worked on a butterfly farm in a Wisconsin town called Luck, running through fields catching monarchs and painted ladies, an oversized net in hand, to be re-homed at botanical gardens. She wrote songs romanticizing life’s highs and lows because she was busy experiencing them firsthand, like a child pressing their face and palms against an airplane window in awe of everything below.
You can hear her embrace this outlook on 11:11 fan favorite “Pavlov’s Daughter.” At nearly eight minutes, it’s a theatrical production on piano that examines neighborly espionage verging on voyeurism, with lyrics that remain open to interpretation. (Is it a call-and-response to Suzanne Vega’s “Luka”? Or is Lucille actually Lucifer, with Regina playing God and Pavlov’s daughter representing humankind?) Most importantly, it’s Spektor’s earliest song that prompts the impulse to sing along dramatically. She molds words in her mouth to sound beautiful or ugly, their transformation dependent upon where in the song they fall rather than their definition: she repeats her name like hiccups (“Regin-AH! Regin-AH!“), drags the end of the word “garb-aaage” like it’s trailing on the ground behind her, and beats the word “quiet” back and forth violently until, on its 22nd utterance, it lays lifeless and still.
As she compiled era-appropriate photos to accompany the reissue of 11:11, Spektor received a USB drive from her father filled with footage of her earliest shows. Her initial instinct was to hide it out of embarrassment, but ultimately she compiled the recordings for the box set edition, handpicking 20 songs that capture her college years and ensuing entrance into New York City’s anti-folk scene. Before Spektor became a doyenne of the genre beside fellow luminaries Kimya Dawson, Jeffrey Lewis, and Diane Cluck, she was doing her part to squash the homogeneity of open-mic bars and cafes. Spanning her first-ever set in 1998 to shows promoting 11:11 in 2001, Papa’s Bootlegs preserves a storied era of her career that’s become difficult to revisit as 404 errors replace defunct fan blogs.
The joy of listening to Papa’s Bootlegs is the feeling of sitting in the crowd experiencing it first-hand: “This is my first-ever standing song!” Spektor declares ahead of “Wasteside.” She laughs shyly while performing the looping melody of “Rejazz,” asking herself and the audience, “How do we end this?” For every slightly off-key pitch or delayed keystroke, there are two belting, goosebump-raising notes. Spektor transposes the jazz and blues artists who inspired her in college—Nina Simone, Bessie Smith, Sidney Bechet—into her performance style, prefiguring her work to come. There’s the gorgeous chord progressions of “Amplifiers” that echo Begin to Hope, the solemn undercurrent of “Train Ballad” like a musical prelude to “Human of the Year,” and a whirlwind of piano runs on “Quarters” fit for Soviet Kitsch. You might imagine Spektor’s father, camcorder in hand, grinning with pride. Occasionally he caves and emits a small “Woo!” while the audience claps.
Barely two years after releasing 11:11, Spektor embarked on her first-ever nationwide tour opening for another New York act, the Strokes. Despite her intimate performance style and oddball songs, she quickly swept to international fame. That impending shift makes the intimacy of this box set all the more rewarding. Previously immortalized through digital file sharing after the CDs sold out, 11:11 is a portrait of an artist who appears too genuine to be human, too creative to be self-conscious, and too curious to be contained. Alongside Papa’s Bootlegs, it’s a time capsule for Spektor’s early days in New York City and a document of the spark that ignited her songwriting career.