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Lisa Loeb

I have a secret crush on Lisa Loeb. When I was 13, I sang every word to “Do You Sleep?” in solidarity with Loeb, alone in my bedroom. The line “You can’t give yourself/Absolutely to someone else” was heartbreakingly true, or so I judged from my middle-school relationships. Later my musical world broadened, but not enough to keep me from watching (and adoring) her quest for new love after the demise of her relationship with Dweezil Zappa on the 2005 E! reality show #1 Single, where she pranced goofily around in her underwear whenever possible and ate half a box of doughnuts on a first date.

So it felt slightly surreal when I finally met Loeb last Thursday — fully clothed and wearing her signature tortoise-shell glasses as she sat beside a micro-fridge in the cramped employee lounge at the Newbury Street Newbury Comics. She was in town for a free show to promote the CD release of The Purple Tape (Furious Rose Productions), which had been a cassette-tape demo for record-label execs and show attendees in New York City in the early ’90s. She recorded the tape, which includes rough versions of songs from her debut album, Tails (Geffen), at an ex-boyfriend’s apartment in the days before “Stay” — the song that her friend Ethan Hawke squeezed onto the Reality Bites soundtrack and that catapulted her into the mainstream music world.

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Re-releasing the album, she said at Newbury Comics, was like “looking at an old photo album and remembering what I was feeling at that time. Some of the lyrics are a bit embarrassing now, but I’m trying not to judge it.” Later she played a 30-minute career-spanning set based mainly on requests from fans who’d packed into the pop/rock CD section to see her. She performed “Stay” and then “Garden of Delights,” another track from Tails. “I wrote this song freshman year of college,” she explained. “I’ve got so many images going through my head of, like, calzones and perms.”

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