Copyright ©2001 PopEntertainment.com.  All rights reserved.

It’s Friday evening at the Upstage; a new Philadelphia venue built in a beautiful old bank building that has been used as a Goth nightclub for the last several years. Lloyd Cole, the Scottish cult-singer who turned some heads with his 80s band the Commotions, is unpacking for a soundcheck with his newest band, the Negatives. His guitarist carries her beat-up guitar case into the club.

She looks familiar, especially if you had MTV in the mid-1990s. It is Jill Sobule, who has recorded four critically acclaimed albums. She even had a fluke smash hit with the 1995 tune "I Kissed A Girl." Sobule has also skirted pop radio airplay with the funny romp "Supermodel" from the soundtrack to the film Clueless and with the beautiful, jazzy early single "Too Cool To Fall In Love."

In ten years, Jill Sobule has released four terrific albums … on three different labels. Hot on the heels of listening to Sobule’s new career anthology I Never Learned To Swim (1990-2000) one has to sit back and think why? Why isn’t Jill Sobule huge? In a world where Puff Daddy (or P. Diddy or whatever it is this week) and Limp Bizkit can move millions of albums, isn’t there a place in the world for a singer who is smart and insightful and funny?

Sobule looks at her stint with friend Cole’s band as a grounding experience. She joined the band soon after she left Atlantic Records in the late 90s and was feeling disillusioned with the music biz. Sobule wanted to remember the feeling of being part of band, driving from gig to gig, where the tour bus is a van, staying in seedy hotels and looking for the local liquor stores in a new city in case she wants a glass of wine after the show. She also contributed to the band’s 2001 release The Negatives. In the meantime, Sobule has continued recording her own music, releasing Pink Pearl in 2000 and doing some new songs for the career retrospective. It is just like the early days in her hometown of Denver.

In Denver, Sobule was a guitarist and songwriter who never even considered singing her own songs. Sobule never tested her voice until she was in her 20s and travelling in Spain. "I didn’t really sing until my third year in college. I did one of those year-abroad programs and I busked on the streets. It was the first time I ever sang my songs, because I thought I’ll never see these people again. So when I was little I didn’t think I’d be doing this."

A publisher from Nashville heard of Sobule and this led to her signing with MCA Records to record her debut album. She was hooked up with notoriously prickly perfectionist Todd Rundgren as the record's producer. Sobule knew she was out of her element the first day that she worked with Rundgren. He invited her to his annual Labor Day party, where a bunch of people sat around doing drugs while watching Jerry Lewis’ Muscular Dystrophy Telethon. Sobule sat on a loveseat with Rundgren’s father, the only two people not partaking of the coke or the has-been lounge singers.

"It was my first (experience) ever in a studio, so I had a hard time," Sobule admits now. "I think working with Todd was probably a wrong choice for my first time, even though I can work with him now. I love Todd. But, he doesn’t necessarily… You have to get to know him and I was so scared and he doesn’t have the best social graces. After a while I started enjoying it. But it took a while."

The debut album Things Here Are Different didn’t make much of a splash when it was released in 1990, although the sultry jazz ballad "Too Cool To Fall In Love" did garner some airplay. Similar in sound to then-popular jazz-based artists like Basia, Swing Out Sister and Sade, "Too Cool To Fall In Love" was also pretty much unlike anything she has done since. But that comes from an immense diversity that has Sobule’s music drawing from all sorts of influences like pop, rock, country, folk, R&B and jazz. Sadly "Too Cool To Fall In Love" was the last song cut off of I Never Learned To Swim, with Sobule explaining "it was between that and ‘Pilar.’ We weren’t sure. Because it really wasn’t a greatest hits (album)…"

Sobule recorded a second album for MCA that was produced by Joe Jackson. It was quite a coup because the iconoclastic Jackson rarely produces other artists' work. But MCA dropped her from the label before the follow-up was released, so that work never saw the light of day. This led to a few years of hard times, floating from Denver to New York, taking any job she could. "I waited tables," Sobule recalls. "Worked for a wedding photographer. (I got back in because) I had friends who had a studio and they gave me time, because I was dirt poor."

The low point was when she was working as a waitress in New York. "At one bar Sandra Bernhard and Madonna came in and did not tip me. I wasn’t a good waitress, but still… That’s always bothered me." Sobule also worked at the famous department store Barney’s. All the while she was stockpiling songs. Finally she was signed to Atlantic Records and her second released album Jill Sobule came out in 1995.

So, perhaps it is kind of funny, at the very least ironic, that when Sobule finally got her big hit… her "K-Tel moment of glory" as she puts it… it was a bit of a joke. "I Kissed A Girl" is an extremely funny story song about a pair of suburban women experimenting with bisexuality. Between the witty lyrics, a kitschy music video (featuring Fabio!) and a bouncy folkish tune (which was rather similar to Sheryl Crow’s debut single "Leaving Las Vegas," which was released at the same time), "I Kissed A Girl" became a left-field smash in 1995.

"I Kissed A Girl" was sometimes written off as a bit of a fluke novelty tune, just a precursor of "lesbian chic." Sobule never bought into that, she was just writing a song. She doesn’t even like the lesbian artist designation. Sobule will only say that she has had relations with both men and women. Any more is none of our business. Still, she admits she was amazed the song took off as it did. "In fact, that would probably be the last song that I wrote… that I’d think would be a hit," Sobule laughs.

That song was followed quickly by the quirky single "Supermodel" which came from the soundtrack to the popular Alicia Silverstone comedy Clueless.  But after that sales for Sobule’s album slowed down. It’s too bad; Jill Sobule was a brilliant album. It also featured "Karen By Night," a story song about a conservative woman who has a double-life where she goes to leather bars after work. It was loosely based on her boss from Barney’s. "Oh yeah, everyone likes ‘Karen,’" Sobule agrees. "A lot of people feel it was a mistake for the label not to put that out as a single. I think each album sort of represents the year before the record…"

Sobule then went into the studio and recorded what quite possibly was her best album, Happy Town. But the writing was already on the wall for Sobule at Atlantic Records. They did release the album, but gave it little or no support. By the time it was coming out, Sobule knew it was probably her last for the label.

Strangely, the first single could have been huge. "Bitter" was sort of a dance music diatribe about the music business. In it, Sobule wondered why she was a struggling while there are other singers who "made it because her breasts were really big." But the tone of the song was a bit bemused with good-hearted resignation, as shown in the chorus, "I don’t want to get bitter, I don’t want to turn cruel, I don’t want to turn old before I have to. I don’t want to get jaded, petrified and weighted, I don’t want to get bitter like you."

That song came from Sobule’s realization that there was nothing she can do about how the world works. She can only do the best work she can and not worry about whether people who may not have as much to say are doing better on the Billboard charts. "I think I did (feel resentful). Not so much anymore. Yeah, you can go, ‘oh, that person stunk so much.’ But it’s wasting a lot of energy. It does no good."

After she was cut loose by Atlantic, Sobule hooked up old friend Cole. She needed a break from the music business treadmill and decided to take a gig on his latest band. But the call of the music was too strong; she was soon signed up again by Beyond Records. In 2000 she released her fourth solo album Pink Pearl. Still, she kept her job with the Negatives, enjoying the freedom both positions gave her. Also, while she was touring with the Negatives, Sobule could play her own music as the opening act.

This led to the 2001 anthology I Never Learned To Swim. This release included some new songs, including a remake of the Fifth Dimension’s "Stoned Soul Picnic" (which had actually been recorded as part of a Laura Nyro tribute album). "Talk about tunes," Sobule says enthusiastically. "(When I was young) I secretly… while I was supposed to be listening to the Clash and the Sex Pistols like my friends, I had my mother’s Laura Nyro and Fifth Dimension records."

Another great new tune from the album is the story song "Big Shoes," an amazing pop tune that sprung from the personal hurt about being teased in school. But the shimmering tune has a way of soothing the insecurity of the lyrics.

"I think it’s probably indicative of the way I deal with my life," Sobule laughs. "You take a depressing issue, and the only way you can deal with it… you can slice your wrists or you can kind of laugh at the tragedy of it. So it becomes a little more theater of the absurd. I can’t be too maudlin. Sometimes I think it’s more effective to deal with an issue where you’re not pounding someone over the head with a depressing minor chord melody. Sometimes I like to switch them around. It makes it a little sicker."