Jill Sobule

Regardless of the size of the bulge in your jeans or the cut of your six-pack, it takes something extraordinary to silence a bar full of horny gay men on a Saturday night—and Jill Sobule's got it. The first time the clip for her 1995 single "I Kissed a Girl" flashed on the TV screen at my favorite homo watering hole, every queen in the place quit yapping, instantly absorbed in the singer's fairy tale of ditching Mr. Right in favor of locking lips with her neighbor Genny.

As the song unfolded, it was the qualities that made the track a hit—an irrepressible melody, coy yet knowing lyrics, and Sobule's unaffected, exuberant delivery—that held the crowd's attention. But what made all conversation grind to a halt in the first place? The heroine's forsaken he-man, portrayed by that epitome of heterosexual masculinity: Fabio.

A few hours before her recent Seattle gig opening for Warren Zevon at Century Ballroom, Sobule recalled coercing the heartthrob to postpone his "I Can't Believe It's Not Butter" commitments to appear in her video. "I wanted the guy I left to be the corniest male icon. It was between him and David Hasselhoff," she chuckles. "We had a meeting, with the director, Fabio, Fabio's manager, and me. And his manager said, 'This isn't talking about homosexuality, is it? We don't want to promote that.' Meanwhile, the director's kicking me under the table, going, 'Oh, not at all.'"

"I Kissed a Girl" sent me racing to procure Sobule's self-titled second album on Atlantic Records (her 1990 MCA debut, Things Here Are Different, is out of print), which turned out to be a treasure trove of character sketches about forgotten classmates ("Margaret"), shoe store managers with secret lives ("Karen By Night"), and teenage girls with runway dreams ("Supermodel," featured in Clueless). Sobule's incisive wit and keen delivery also yielded some remarkably truthful takes on romance, including the kiss-off "Good Person Inside" ("Whenever I think what a dick, what a liar/I try to remember the good things inside").

Sadly, 1997's Happy Town didn't measure up to its predecessor, in songwriting quality or sales, and her label dropped her. But Sobule soldiered on, playing guitar with Lloyd Cole's band, the Negatives, and serving as a political commentator for a New York radio station, penning original tunes inspired by current events. Based on the handful she featured in her Seattle set, including "Kathie Lee's in Love with Me" and a chipper number about the death penalty's popularity in Texas, let's hope she cuts a whole disc of these tunes soon.

Fortunately, at least one of them made it on to her forthcoming Pink Pearl (on Beyond Music), a winning return to form. "Mary Kay" recounts the infamous Washington schoolteacher's seduction of a student and subsequent conviction with surprising sympathy. "That one came to me after watching Court TV," Jill reveals. "I thought, 'What a modern-day Greek tragedy.'"

"Lucy at the Gym," another one of the album's many gems, shares parallels with the singer's own teenage years. Like the song's body-conscious subject, who climbs a Stairmaster to Heaven, Sobule once suffered from a poor self-image. "Before it was well-known and there were TV movies about this, I had an eating disorder," she admits. Since then, she's avoided any strict diet or exercise regimen. "I try never to put myself on any kind of restrictions and say 'You can have this, you can't have that.'"

While high school is a recurring theme in her work (including Happy Town's "Underachiever"), Jill's own experience in Denver was remarkably pleasant once she'd weathered eighth grade. "I decided I wanted to reinvent myself and went to parochial school," she discloses. "I was one of the only Jewish girls in a Catholic all-girls school. We had really cool uniforms, which I wish I still had. This fall I went to JC Penny and bought the large-size girls' back-to-school Catholic uniform." And then Britney Spears went and ruined the look for everyone. "Damn that little bitch and her fake boobs," she laughs.

"Heroes," Pink Pearl's most biting track, rattles off a roll call of icons who've disappointed the wide-eyed blonde, from Pablo Picasso and Orson Welles to the author of Seven Years in Tibet and the Old Testament God (who can be "so petty"). "I used to idolize Dorothy Parker," the singer explains. "She was so witty. And later you realize she was just a mean, hateful drunk." But that's not what prompted her to pen this litany of couplets like "Paul McCartney, jealous of John/Even more so now that he's gone/Dylan was so mean to Donovan in that movie." What did was learning that one of her favorite poets was an anti-Semite. "I adore T.S. Eliot, but he was an asshole," she concludes. "Plus he gave us Cats."

Pink Pearl (Beyond Music) will be released Tuesday, April 18.

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