In 1994 when Lisa Loeb’s breakout song, “Stay (I Missed You),” landed at No. 1 on the charts it was a remarkable and unparalleled feat for an unsigned artist. Though perhaps not a surprising one for the recent Brown grad, the girl with the cat-eye glasses, who at the time was already making her mark in New York’s burgeoning singer-songwriter scene. For anyone who knew her back then, or who saw her perform at various clubs around town including the Cottonwood Café, The Bitter End, the Bottom Line and CB’s Gallery, it wasn’t a question of if, but when Loeb would hit it big.

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