Jill Sobule's summer-vacation success with "I Kissed a Girl" almost sank her in cement as a one-hit wonder, even though that fun tune surely got her all the dates she could endure for a while. Sporting a potentially dismissable, fresh-out-of-fourth-grade, alt-cute girl voice, she could easily fall into the princess-sized crack somewhere between the careers of Suzanne Vega and Liz Phair, and it's just too soon for that. But our girl has grown up, it seems, for on Happy Town, Sobule's third and clearly most serious album, she proves to be not only a contemplative lyricist with a sense of humor but a competent arranger as well, adding wisps of well-placed clarinets, smoldering guitar work and Latin grooves to her busy tracks. With its itchy, poppy, hip-hoppy motions, "Bitter" makes for a compelling and innovative single, something to be proud about in this business. But the most unusual and memorable single may be "Underachiever," the poignant tale of an oversensitive high school history student who loves to gaze the hour away at her teacher without thought to her declining grades. It's great to confess a love for this stuff, from the indulgent adolescent subject matter to grown-up musical moments. Glad the girl stuck it out.
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AllMusic Review by Becky Byrkit