Exclusive interview with Jill Sobule by Caty Simon. Jill appears this Saturday at the Iron Horse at 7PM.

"It's great that a song like that can piss off "Focus on the Family," and still be on the radio."

Singer/songwriter Jill Sobule rose to fame on the strength of her 1995 hit single "I Kissed a Girl," a tongue in cheek nod to the media's fascination with "lesbian chic." Born in Denver, CO in 1961, Sobule grew enamored of rock music at a young age, but did not seriously consider a career as a performer until she spent her junior year of college abroad in Spain. Upon her return to the U.S., she dropped out of school to devote her full energies to music, but her work found little success as she battled with depression and anorexia. In 1990, Sobule finally made her debut with Things Here Are Different, which the songwriter recorded with producer Todd Rundgren, (who recently played the Iron Horse, a testament to that particular stage's hallowed history.) The album vanished from sight upon its release, however, and she was dropped by her label, MCA. Disheartened, Sobule moved to Los Angeles and took a job as an assistant to a wedding photographer. Sobule's fortunes turned when her lawyer played her demo tape for an Atlantic Records executive, who was so impressed by the contrast her winsome, folk-flavored pop offered in comparison to the then-current chart dominance of grunge that he quickly signed her to a contract. After the 1995 release of Jill Sobule and the subsequent popularity of "I Kissed a Girl," she scored another hit with the satirical "Supermodel," which was featured prominently in Amy Heckerling's comedy smash Clueless. The LP Happy Town followed in 1997, impressing critics with a new level of depth and maturity; unfortunately, it didn't match Sobule's level of commercial success, and Atlantic dropped her from its roster. (Jerks!) She took some time off from her solo recording career to regroup, and joined Lloyd Cole's new backing band The Negatives (also featuring our friend and my old house-mate Dave Derby, former Dambuilder, current Gramercy Arm) as a guitarist in 1999. After landing a new recording contract with Beyond, Sobule returned in 2000 with a new album, Pink Pearl. In the years that followed, she dabbled in off-Broadway musicals, made an appearance on NBC's West Wing, composed songs for a Nickelodeon series called Unfabulous, and played a busking musician in the indie film Mind the Gap, a movie that featured songs included on 2004's "Underdog Victorious."

I asked my friend Caty Simon to do an interview with Jill, who plays the Iron Horse this Saturday, May 9th at 8PM. Caty had responded enthusiastically when we announced the show and I thought that pairing these two creative women for a conversation would be worthwhile. I was right.

Caty: You're very open about depression and decompensating in your lyrics. You don't shy away from talking about staying in bed all day, or being the crazy girlfriend that smashes her boyfriend's windshield. But you don't glamorize it in any goth or grunge way, either. Could you comment on that?

Jill: I guess for me somehow mixing an angst lyric or story with bombastic or similar feeling music seems too much. In fact sometimes I like to play with the exact opposite. It can sometimes end up being more uncomfortable and wrong (in a good way). Plus, I think, I do have, no matter how grim something seems, that light at the end of the tunnel thing. And, sometimes, I will throw in a "joke". That's how, in my real life, I have dealt with...stuff.

Caty: Do you think you get pigeonholed at all as a "joke" songwriter? What can you say about the use of humor in your songs, and how it affects how you're perceived?

Jill: One time I was playing a show at a college and I saw the banner for me that said, "Jill Sobule -Stand -up Comedian." I was upset at first , then ended up doing the most depressive angry set ever. Although I did do one joke -one very blue joke. But yes, I have had to deal with that. I remember Warren Zevon telling me "I Kissed a Girl" was my "Werewolves in London."

Caty: Every album of yours contains such an eclectic use of musical styles, it's hard to tell what your influences are. In fact, in "Heroes", you denounce most of the influences you do mention. Can you tell me about the musicians, writers, and artists that inspire you?

Jill: Your right. I love music and I have such a wide range of taste -if you saw my iTunes collection... Boy, lyrically, I probably was influenced by those iconic writers that told stories and sometimes...used humor. I'm thinking Randy Newman, John Prine, and even Joni sometimes ("watching your hairline recede my vain darling.") But, musically, I wasn't so much a folky. I grew up being obsessed with Bowie.

Caty: Can you tell me about what it's like to be mostly known for one song--1996's "I Kissed A Girl"? Do you ever get resentful about being roped into the "lesbian chic" trend of those years?

Jill: It was sometimes irritating to be "the kissed a girl girl". Or rather, that that was, sometimes, the only thing that people knew about me. However, I am proud of it. It was the first, I think, blatant "queer" song to make the top 40. Of course now Katy Perry has taken the title and made it her own. More power to her, however I will say, hers' is more of a "girls gone wild" thing. The intent of "the Classic" (someone referred to my song as that) was hopefully more to empower and explore one's sexuality as more than just a fun thing to turn on your boyfriend. That said, I still think, it's great that a song like that can piss off Focus on the Family, and still be on the radio.

Caty: On a related note--since this is Northampton-- can you talk about your relationship with the queer community? You've written a bunch of songs about the problems queer youth face: "Underachiever", on your third album about the correspondence you had with a closeted lesbian high school student who wrote to you for help, and how her experience reminded you of your own high school days with your crush on your history teacher. There's "Underdog Victorious", too, about an ostracized gay kid who dreams of his future success, and the song "Under the Disco Ball" is about a gay boy who grows up in a Christian household. After "I Kissed A Girl", you were featured in a number of lesbian magazines. But what's your reception in the lesbian community been like since? Has the lesbian community continued to embrace you, or do you feel that they're unwilling to accept you as bisexual woman who mostly dates men? I remember reading an interview with you once where the interviewer asked if you ever considered playing the pronoun game in order to make your songs universally appealing to people of all sexual orientations, and you said you didn't want to do that, b/c that would be just like what you did in your first album, in which you chronicled your relationship with a woman, but you were too scared to be out and used "you" instead of "she" and "her."

Jill: When "I Kissed a Girl" came out (1995), it was a tough call on talking about my sexuality. I wanted to talk about all the songs, but all anyone wanted to talk about was "so, what are you?". I didn't want to be an exclusive queer artist-only to play the "womyn festivals". At the same time, the idea of the song was to celebrate the joy of that first same-sex kiss and I did not want to underplay that. Since then, I have developed a diverse fan-base with a good sized gay following.
And, I did play that...Womyn's festival. The community is very important to me. I am part of the family.

Caty: You seem to love to tell stories in your songs. It's not that you don't also write confessional music, but your fascination with other people's lives is clear from your lyrics. I'm thinking particularly of "Karen by Night", a quirky song about a shoe store manager who leads a double life as a motorcycling dominatrix. Many of your songs are a fun musical equivalent of people watching. What started your fascination with chronicling other people's lives in your songs?

Jill: I think it started by reading - "Harriet the Spy"? If I wasn't going to be rock star growing up, I wanted to be a detective. But it's not just voyeurism. I think I relate to each of the characters I write about. In some way, I am(or we all wish we could be) "Karen By Night."
We all keep secrets. We also wish we could, "let the freak flag fly" sometimes.

Caty: So I have to ask how you got the brilliant, original idea to fund your latest album solely through audience anticipation-- you put up a website asking fans to contribute, and a ten-dollar donation bought a digital download of the album; a hundred-dollar donation brought a hard copy of the CD, a “Junior Executive Producer” T-shirt, and a mention in the liner notes; a five-hundred-dollar donation earned mention in a song. There was even a ten-thousand-dollar level that would let a fan sing on the record. It was a wildly successful scheme. How'd you come up with this?

Jill: It was something I have thought about for a long time. The idea of going into another A&R office, hoping they'll give me another record deal, sounded just awful. I would have payed for the new record all by myself, but was completely broke. I didn't want the fans just to...give me money, so I came up with different levels of "gifts and services" for their donations. It turned out more successful than I had ever thought. I'm glad, actually, I didn't have the money to do it
myself. It has increased the communication and appreciation between myself and the ones who matter the most these days -the fan.

To be continued.....