We’ve Got A File On You: Jewel

Dana Trippe

We’ve Got A File On You: Jewel

Dana Trippe

We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

Jewel Kilcher is a badass. Over the years, particularly at the start of her career in the mid-’90s, much has been made about the fact that the singer-songwriter grew up in a frontier-like setting in Homer, Alaska, without indoor plumbing and “living off what we could kill or can,” as she once put it. Every profile you read about Jewel will mention that she was at one point homeless, living in her van, before breaking through on tour with eventual mentors Bob Dylan and Neil Young. But even after achieving global fame via 1995’s Pieces Of You and its 1998 follow-up, Spirit, Jewel was put through the industry wringer many times over. She still doesn’t get enough credit for her strength, candor, and strategic decision-making.

At the moment, Jewel is preparing to release, Freewheelin’ Woman — her first album in seven years and 13th overall. It’s produced by Butch Walker and finds Jewel leaning more into her vocal capabilities as opposed to songwriting and lyrics being the primary focus. Jewel also wanted the album to reflect her role as a single mom (she shares a son, Kase Townes Murray, with ex Ty Murray). “It was a really intense process writing this album,” she says over the phone. “This industry’s notoriously unkind to women and even more unkind to women as we age. We lose a lot of women songwriters because it’s so difficult. It’s difficult to be a mom and have your child in school and be a musician. I really haven’t seen many women talking about it. You’re supposed to kind of pretend you don’t have kids, you’re supposed to pretend you’re not middle-aged, you’re supposed to pretend like you’re a sex kitten forever, and I thought that that’s really distasteful.”

Jewel’s frankness is arresting, but what is even more striking is the fact that she’s always been this way. Even as a much greener performer, Jewel was iconoclastic and decisive, often performing multiple shows in one day, turning down seemingly major career opportunities (to her management’s chagrin) and, at one point, controversially pivoting her sound from folk to straightforward pop. Through it all she fought against sexism from record execs, radio DJs, and journalists. Read on for Jewel’s brutally honest stories from a career that’s now thirty years strong.

Freewheelin’ Woman (2022)

What were your intentions surrounding Freewheelin’ Woman? Are you doing anything on this album that you perhaps hadn’t before?

JEWEL: When I got discovered, I almost didn’t sign the record deal because I was, I think, soberly aware of the fact that I had a lot of emotional baggage and that God forbid somebody like me get famous — it’s a recipe for what we’ve seen all too often in the music industry. Substance abuse or death, or unhappiness, all of which were unacceptable.

So it absolutely really frightened me. I was afraid to sign the record deal because during that year that I was homeless, I had just started learning how to be happy. As odd as that sounds, I’d started getting a grip on my panic attacks. I started really healing my agoraphobia, and I didn’t want to trade that. I wasn’t optimistic that fame would be good for me. I made myself a promise that I would always make my number one job to learn how to be a happy, whole human and not a human full of holes. My number two job would be to learn how to be a musician, and that my goal would always to be to support art over fame.

So those are the two north stars that I’ve navigated my career by. It’s why, especially in context of that first choice, I would always choose how to be happy over fame. That’s why I took like two years off at the height of my career way back after “Hands” was a hit. It’s why I’ve taken years off between records to psychologically adjust. It’s why I’ve taken the risks I have musically and switched genres because I felt like that was good for my music.

So bringing us up to speed here to this album, I was a single mom, I had gotten a divorce and realized that touring constantly with a child is obviously not great for a child. So I took several years to focus on [being a] mom and on just healing after the divorce, and decided finally that it was time to start making a record. I wanted the record to really represent who I am now. This is the first record I’ve written from scratch, every other album I’ve had thousands of songs in my back catalog, and so could always just pick songs out of my catalog without having to write the album.

So to me, this album is a celebration. I feel like I’m at the heights of my ability. I feel I’m singing better than I’ve ever sang. I feel I’m writing than I’ve ever written. I’m really proud of who I am. I feel really empowered. I feel proud that I’ve gotten to live life on my terms. I’ve gotten to have my career on my terms. The reason I called the album Freewheelin’ Woman is because that’s how I feel. I’ve fought for my autonomy, I’ve fought for my liberty as a woman, and been able to make a living, and even support my child on my thoughts and my ideas and my feelings. I’m proud and I wanted the record to encapsulate that whole feeling.

I’m struck by everything that you said about your mentality going into signing a record deal at the beginning of your career and where that’s taken you since. In the last couple of years, there’s been a major reckoning around the way famous women were treated by the media in the ‘90s and ‘00s. Did any of that discussion in the last couple of years resonate with you, based on what you’re talking to me about now?

JEWEL: Certainly. My whole career, the slant that the media gave it was through a really, I dare say, patriarchal lens. You think of my origin story, right? The whole world knows I lived in my car. They think because I was fighting for my dream of music. That is an absolute misrepresentation of what happened. I was living in my car because I wouldn’t have sex with my boss. I refused to be leveraged and he wouldn’t give me my paycheck and I couldn’t pay my rent and I started living in my car and then my car got stolen and I was homeless because of that, because I wouldn’t bang a boss.

I said that at the time, I said that in every interview, but it was almost like people didn’t even have the ears to hear it. They would just write the story, “Jewel lived in her car to pursue her music career.” That’s not why I lived in my car. I was not even thinking I would be a musician. I was trying to figure out how to stand up for myself, how to refuse to be leveraged for anything or anyone. It was an active defiance, it was an act courage. It cost me a lot, but it won me myself. It won me my humanity. I’m so proud of that decision. It was so funny to see it portrayed as some cute, fluffy little, “Aw, she was fighting for her dream.” I didn’t even have a dream. It’s not what I was doing.

When I took years between records, it was like, “Oh, where’s Jewel? She’s a has-been, she’s washed up, she couldn’t cut it.” None of that was true. I took two years off at the height of my fame after “Hands” because I couldn’t psychologically handle the adjustment and nobody cared about psychology. Nobody cared if you were doing well, they would offer you drugs and just want to keep you touring because that’s how you made money.

So it was again very funny to have that portrayed in the media as if it was a disempowered thing, when it was an empowered thing, it was a difficult choice. Again, fighting for my humanity, for my psychology, for my happiness. In the ’90s, when I was doing radio interviews, I would go in there and they’d say, “So, Jewel, how do you give a blowjob with those fucked up teeth?” Live on air.

I would go, “You know what? I can fix my teeth, but you’ll never fix being stupid.” And I’d get kicked out of the radio station. They kicked me out. I got escorted out of so many radio stations because I wouldn’t take shit. My label was like, “Jewel, would you please?” And I was like, “I will not. I will not let anybody talk to me like that.” I remember South Carolina live on air, “Hey, you may have heard me describe my next guest as a large breasted woman from Alaska. Jewel, how are you?”

I said, “You must be the small penis man I’ve heard so much about from South Carolina.” Escorted out of the radio station. Like, that was just life. That’s what life was like. Even my lyrics that were at the heights of grunge, I was writing about sensitivity and kindness and those things. The cynicism that that was met with, I would be called Pollyanna or that I was some kind of cult figure with like a cult following. Not in a good way, [but] “cult following,” as if we were all stupid.

Then the Spice Girls, right? I think “Hands” was a hit at the height of the Spice Girls. So my whole career has been a complete anomaly because I write songs that are very sincere, they’re heartfelt, and it was never that cool.

Facing Off Against Kurt Loder On 1515 (1998)

Looking back at an interview you did with MTV to promote your book of poetry, A Night Without Armor, Kurt Loder seems to have bought into that “Jewel is uncool” narrative. Did you ever get an apology from him for the condescending way he spoke to you and about your book?

JEWEL: Poetry was my first medium. I have thousands and thousands of poems. I write every day. It was definitely before songs. There’s been years where I don’t write songs, but I still write poetry every day. When I really, really wanted to release that book and no publishing company wanted it — because poetry’s wildly unpopular — I had to bribe them with an autobiographical book. I was like, “If you let me first, I first want to publish a poetry book. [Then] I’ll give you something.”

So they agreed to that, and much to even my surprise, that book became the best-selling poetry book of all time. I don’t know if that’s still true, but at the time the publishers told me that, and it really shocks people. It also is funny. It really upset people. Poetry is a darling of the literary crowd and to have a pop singer write a successful poetry book. I don’t know why that book really pissed people off, and it was met with a tremendous amount of cynicism.

But my whole career had been met with a lot of cynicism. Nobody liked that I was writing about being sensitive and kind. It was made fun of. Which I found weak. I found cynicism to be easy. Cynicism is a very easy coping mechanism to hide your dreams, your aspirations. The more cynical you are, is usually the more sensitive you are. You’re just hiding behind this mask. I felt that was cowardly. So I had a really strong opinion about cynicism, that it was as cowardly as it was a disservice to audiences to hide and to pretend behind this mask, because you only become cynical and bitter if you feel like you had this dream that didn’t get met and you gave up.

All that to say, I was pretty used to that feedback by the time the poetry book came out. But I was also very tough, right? Because the poetry book did so well, I think because it had this very honest… I mean, when I did TRL, I did a poetry reading on MTV. I don’t think that’s ever been done. The ones the kids wanted me to read were rough. They were about unprotected sex and really, like, rough, raw poems. These kids, it was like what Bukowski did for me or what Anaïs Nin did for me. They took the veneer off of life and I felt proud that.

Not that my writing was brilliant, but I felt proud that I was willing to take the veneer off and to be met with this appetite that people wanted that. So when I did the Kurt Loder thing, I mean, I was kind of prepared for some cynicism, but when he was setting me up, I couldn’t figure out why he was setting me up. It was something about a word, right? Grammar, I think.

He corrected your use of the word “casualty” versus “casualness.”

JEWEL: Yeah. I used the word incorrectly. He was setting me up, and then he dropped the hammer or something as if to expose me that I wasn’t educated or something. Did they put in when I said, “Fuck you.” Was that in that?

The transcript is still out there. You call him a smart-ass.

JEWEL: Wow. That’s amazing. Yeah, I just remember looking at him and like saying, “Fuck you.” I am uneducated, straight-up. An uneducated kid that was homeless. You’re a college-educated man going after a kid, “Fuck you.” I was so pissed. No, no apology. No, he was just a dick. What an ass to show himself like that. It was almost that thing where you’d feel sorry for somebody, it’s like, “Wow, here’s a full grown man who does news for children, on a children’s network, for teenagers.” Yeah. You’re bitter.

Ugh. Well, I’ve certainly run into my share of those more-educated-than-thou types in the journalism world.

JEWEL: One of the articles that always made me like laugh — just since we’re getting into journalism and articles — is my second Rolling Stone cover. I really connected with the writer. It was one of those times — I don’t know if this still happens — where the writer hangs out with you for multiple days.

It’s very rare these days.

JEWEL: We really hit it off. We both loved like the The Master And Margarita and just kind of obscure Russian literature. So on the last day I was like, “Just stay in my guest room. You’re welcome in the house, stay in the guest room.” In the article, he made it sound like I didn’t leave the room. I went into his room, I made sure he had towels, and of course I left and went to bed. He just never put a button on it. He kind of insinuated that I stayed the night with him.

I was very upset, like very upset. I called him. I was like, “What the fuck?” Like, it’s my honor. You know what I mean? I was so fucking pissed. But the thing comes out, it’s promoting the second album Spirit, “Hands.” I sit down with, I think, Entertainment Weekly. We’re in my hotel suite, in the living room, I’m doing a press junket. The guy comes in, his opening line is, “Wow. I read the Rolling Stone piece. So I guess if you don’t kiss me in the first five minutes, I should be insulted.”

Uh, what??

JEWEL: I said, “Fuck you.” That was how the fucking interview started, and there’s nobody in the room with me, there’s no handlers.

I go, “Fuck you.” And we fucking went at it. So, of course, they have the power because they’re writing it. So in the cover, I think it was like I’m portrayed as a diva — it says diva, I think maybe on that cover, and in bold quotes. I think the quote is something like, “All of these fucking journalists do the same. You’re a carbon copy of a carbon copy. You don’t have an original thought in your head.”

So I was just so fighting back and it’s a helpless thing. There’s no fighting back, they’re going to win, they print what they need to print. Don’t get me wrong, I’ve benefited from press, right? But I never did take it sitting down.

I am so sorry that happened. That must have felt incredibly violating.

JEWEL: I lived the life, I stood up for the things I wanted to stand up for, and you do it because it’s the right thing to do. But it is fun to be around long enough to be able to talk about it.

Guest Hosting MTV’s Alternative Nation (1996)

Did is seem strange in the mid-‘90s that the industry wanted to classify your music as “alternative”?

JEWEL: There was really no place for somebody like me. My music didn’t fit within a genre specifically. I mean, I was definitely folky, but there was no format for folkish. Americana wasn’t even a genre, right? That’s a brand-new word. “Alternative” as music at the time was the most accepting wide subject, if you will. I was able to sort of sneak in alternative, which I was really thankful for. I mean, it was hard to find a space for me. That first album failed for multiple years and we just kept fighting. The label, amazingly, stuck with it.

I remember when I heard “Who Will Save Your Soul” play between Nirvana and Soundgarden — [it] made no sense, but I’m all for it. I was just thankful that anybody was willing to take a risk because I was laughed out of every radio station. I was told by every club owner and radio promoter that there would be no place for me, that [my] music wasn’t relevant. But I just on the street was seeing something different. I feel like grunge ripped the scab off of a wound, of a generation of people that didn’t feel like happy, shiny people in Madonna and glam rock’s beautiful world. They felt unhappy.

Kurt Cobain gave a voice to that unhappiness, but you can only feel that badly for so long before you kill yourself, and my music just happened to be about, “Okay, I don’t want to kill myself. So what do I do about it? How do I handle this?” Because I have to take all this pain and figure out how to transmute it. So I was seeing that that was relevant. I’m playing clubs and in coffee shops and on college campuses. It’s just that the gatekeepers didn’t see it. Thankfully I was able to stick around long enough till the time shifted.

Performing “She Cries” At The Arthouse In Carlsbad, California (1994)

Speaking of those really early performances, what did the year before Pieces Of You’s release look like for you? What would a day in the life look like for you in 1994?

JEWEL: So when I got discovered, there ended up being a bidding war over me and I turned down a million dollar signing bonus as a homeless kid because I had read a book about how the business works. That it was a loan, basically. I owed that million dollars back through record sales and that I would never make any more money until I paid that money back.

The reason I turned it down is because I felt like that front-loaded pressure on art, right? So going back to my number two goal was to learn how to be a musician and caring about art more than fame. So I felt like taking a million dollars was basically putting a bounty on a baby kid, despite the kind of heat that was around me during that signing frenzy. I didn’t want to put that bounty on my little record because that’s how artists get dropped. If you don’t recoup in a certain amount of time, the label just cuts their loss and like, “All right, didn’t work.”

’94 was a tough year. I sold maybe 2,000 copies [of Pieces Of You] in a year, all in San Diego probably. So I realized, you can’t be more talented than somebody else, right? You’re on a label with 600 other artists, you’re in an industry with thousands of artists, you’re not going to out-talent somebody, but you could outwork somebody. So I felt like that was really one of my only competitive advantages. I was willing to outwork people.

I also had to fight. Like, I knew I was making music that people weren’t dying to put on the radio. It meant I had to get gritty and stay gritty and stay very determined. So that year I think I did over a thousand shows. I was doing four shows a day minimum, up to six shows a day. I was singing in high schools in the morning and it was part of this thing called Earth Jam. They would pay for my rental van. I never took a tour bus. I kept my costs extremely low. I was costing a label nothing. So while I kept failing, the label had no reason to drop me, because they never got into a meeting and went, “Holy shit, this line item of Jewel, why is this costing us so much?”

So I was just cheap and worked hard. I did coffee shops or high schools in the morning. Then I would do usually two radio shows, at least one record store, a show out in the parking lot. Then I would open for somebody like Peter Murphy of Bauhaus at night. I paid him to open for him. I paid him $500 a show. Then I did a solo coffee shop gig at midnight. That was my day. I did that for over a year. I would do these little circuits where I called it “hard wood grows slowly.”

I’m ambitious, right? It doesn’t mean it’s going to work, but my ambition was to be one of the best singer-songwriters of all time, which is a really ambitious, crazy goal. But it meant, again, always putting the art first. It meant “hard wood grows slowly,” meaning I wanted to be around for 60 years. If you grow too quickly, that’s bad for a long-term arc. There’s no shortcut to building something that hopefully lasts a long time.

So I had really long perspective and that made me make weird choices. I did these residency tours. Nobody had ever done them. I don’t know if people have done them since, but I would basically play Boston every Monday, I’d play at Philadelphia every Tuesday, I’d play New York every Wednesday, I’d play D.C. every Thursday. You get the idea. I would do a circuit, and I would stay there for one to two months. Maybe three people would happen to been there in my first show, then it was six people, then it was 20 people, and then maybe a hundred people. So I built very, very grassroots that way. I toured like that doing thousands of shows a year for at least a couple years until that album actually started to take off.

The Masked Singer (2021), Extreme Makeover: Home Edition (2006, 2010), Ace Of Cakes (2010), Nashville Star (2008), Dancing With The Stars (2009)

Over the last 10 to 15 years, you’ve appeared in a number of reality shows about music but also spanning subjects like baking and lifestyle. You won The Masked Singer and represented Alaska on the Eurovision-inspired American Song Contest. How does TV fit into your overall career strategy?

JEWEL: Again, it kind of always comes down to what my main goals are. Going back to the beginning of my career, I was offered to be on The Real World, which was the very first reality TV show. My label was super pumped about it. I hadn’t even made my record yet. And it was in Northern California, it was the season that ended up being huge. They were like, “You’re going to live in this house. You’re going to go from living in a car to making the record on television. The whole world will get to watch it, and it’s going to be a huge thing for you.” It didn’t fit my strategy of hard wood grows slowly. I felt like it front-loaded too much visibility when I hadn’t earned my stripes. It didn’t stand for what I wanted to stand for. I was a songwriter, I’m not a reality star.

I turned it down, which my label was really shocked by. I took the hard bitter pill of working my way into oblivion, but that paid off and that fit my strategy and I felt like I got to be known for what I wanted to be known for on my own terms. It’s a risk, but I mean, hey, luckily it worked out.

Later in my career now, I’m a mom, and so my strategy has to be really different. I cannot go promote a record for two years. I will not go tour a record for two years. I really won’t promote something in person for more than a couple weeks and maybe will tour a couple months. So the strategy has to change from when it did when I was young. Especially as a mom, because my son’s in school, I have a really different pressure on me than I think male musicians do — especially as a single mom. So doing a show like the The Masked Singer just fit my strategy, right? It took very little time to film, I could keep my son in school. It’s kind of a risk because it’s a cheesy show, but it also let me do something I really wanted to do, which was really just show off my singing, which I’ve never had a chance to do.

So you just weigh all that out and you go, “It’s a cheesy show, but it checks my box of letting me be a mom, it helps me promote an album that’s going to be coming out in no time.” So you make different decisions. The TV shows that I do are really kind of, what are my main priorities and does it help me achieve those. And I do, I think it’s really different. It’s different for a mom, it’s different when you’re middle-aged. You’re making different decisions.

Performing At (But Not Hosting) SNL (1998)

Still on the subject of TV, you’ve spoken before about regretting turning down an offer to host SNL in the ‘90s. But at the time, did you also think that hosting would also be too much exposure?

JEWEL: I remember making the decision. I was flying back from Zurich. What year was that? That was probably during “Hands.”

So I was doing at least a thousand shows a year for multiple years in a rental car. Exhausting doesn’t even begin to come close to describing that. Then I hit. So then you’re capitalizing on this. It has its own momentum. I went from selling 2,000 albums in a year to, at some point, selling a million albums every month. It took on a life of its own. It was an insane pace. I hadn’t broke Europe and I always wanted to break Europe because I felt like that’s incredibly loyal fan base. Long after your star has faded in America, you can go tour Europe and make real money. I thought that was a good insurance policy and I just really cared about Europe.

I would go from selling out huge 15,000, 20,000-seat venues here in the States, and I would go open for Willy DeVille in Europe. Crappy. I just had a fist fight with Europe. They were not having the folk music at all. But for whatever reason, that real scrappy part of me just kept going over there, and it was just brutal. All that to say, I was really tired, so I never rested once I got there. I went right into making “Hands.” Thankfully, “Hands” worked well, but I was really tired. And then I filmed that movie for Ang Lee [Ride With The Devil], which was really stressful. Really fun and really stressful.

I was flying back from Zurich. I was really sick — I had pneumonia, and they offered hosting Saturday Night Live, which is an incredible honor. But I was near mental-health breakdown. I was exhausted in a way that is hard to describe. The psychological adjustment of the level of fame that I suddenly achieved was really, really difficult. It’s so hard to describe the psychological pressure of that level of fame, and who wants to go therapy, right? You’re rich and you’re famous and you’re living your dreams. It’s not a really pitiable thing, but that’s why you saw Mariah Carey, — did she have a mental-health [breakdown]? I feel like she had been hospitalized. [Editor’s note: Mariah Carey was indeed hospitalized in 2001 for “extreme exhaustion” in 2001.]

Too many artists have mental health breakdowns, and I was like, “Yeah, this is how it happens. This is a shit show.” I remember telling my team, “I can’t do it. I do not have the reserves. I don’t have the capacity.” It is a regret, looking back, I would’ve loved to host it. I’ve never gotten to show like my humorous side, unless you really see me live, I do a kind of standup, but it was never really out in the public eye and it’s something I wished I could have done. I just couldn’t, I didn’t have the reserves in the tank.

It probably pissed them off, by the way. I’m probably the only person that’s ever turned it down and it probably made them hate me. I mean, it’s just like, “Oh god.”

You did end up performing on the show in the fall of ’98. There’s a funny clip of the late Norm Macdonald talking about meeting you that week.

JEWEL: The cast was wonderful. But yeah, I always wondered if I just pissed them off. Like, “Who the fuck does this girl think she is?”

Roasting Rob Lowe (2015)

Well, since then, you have had the opportunity to show your humorous side, specifically on the Comedy Central Roast Of Rob Lowe, where you joked about not wanting to kiss him when you were both acting in The Lyon’s Den. We can joke about it now, but what was going through your mind in 2003?

JEWEL: I loved acting. I’d always wanted to have a double career. I liked acting because it let me explore psychology in a way that writing doesn’t. It’s very different when you have to act out that psychology over the arc of a movie. But as I got into really what acting takes, the auditioning process is pretty humiliating. It’s these cattle calls, they want to look at your body, it was really like, “Wow, this is dehumanizing.” You go in auditions for things like Swordfish, where you had to show your boobs.

I was just really appalled at the time of what they were asking women to do. I turned down that Swordfish audition because I was like, “I’m not going to show my tits.” It’s so gratuitous in the scene. At the time I was just really keyed onto that. My whole career [had] to be taken seriously — there’s so much more to me than my sexuality. So in the Rob Lowe thing, I just pushed back because I always push back on, “Yeah. Are these things gratuitous? Is it really important to the scene?” Like, “Is there another way to write this?”

So I push back and [my] agents, everybody was like, “What the fuck? You’re an actress.” Like, “Do your job.” Which is fair, I totally get it. I just couldn’t help but question it. I did end up kissing him, but it was apparently a really big deal that I even brought it up and pushed back. It is so funny. It’s very funny that that’s what made his biography. That that was actually a note in his biography that I didn’t want to kiss him. Apparently it was a radical thing.

The roast was super fun. If you’ve see me live, especially in theaters, I do a ton of stand-up. It’s all improv. I’m really kind of rotten, my audiences have always just been incredibly gracious with me. But it’s nothing I’ve ever been able to do like on television or a larger scale. So the roast was kind of a fun opportunity, except I’d never done that type of stand-up that was a legit thing. It was definitely one of those kind of high-risk things — like if I won, it would be winning big, and if I failed, it would be very, very public. There’s just no way to hide failing at stand-up. It is what it is. So it was a scary thing to do, but I really enjoyed it.

“Intuition” (2003)

When you were preparing to release “Intuition” and the accompanying album 0304, what was the industry pushback like, if any? It was a major shift in your overall sound and aesthetic. Did you get more of that “just do your job” kind of rhetoric?

JEWEL: I grew up loving Cole Porter, his intelligence. He was so pop but so smart.

I had been experimenting on the prior album [2001’s This Way], like with “Serve The Ego” and a bunch of dance remixes where I started to get into electronic music. The idea of kind of reinterpreting folk music, classic storytelling lyrics, but in a pop setting. This is before like David Gray or those things. It just kind of wasn’t happening or it wasn’t a genre yet.

My whole thing, my whole career was save your money so that you could make any art you like. I never had to have a record be successful. So that lets you take risks, that lets you fail. So I knew it was going to make a popper. I knew it would be really controversial, because in the ’90s, credibility was everything. Selling out was a big deal. For women, you had a tremendous amount of extra pressure on because there weren’t many female singer-songwriters. You’re held to this real standard, and so were the men — just credibility-selling.

I felt like selling out was repeating myself. I felt like selling out was doing what people expected me to do and being afraid to be authentic. So for me, the pop album, it was funny that it was considered a sellout when it was the opposite. To me, selling out was never changing because people wanted to do a “You Were Meant For Me” 2.0 or 3.0. Maybe the world would’ve been happy if I made “You Were Meant For Me” 2.0 and 3.0, but I would’ve known I was selling out. I would’ve known I was playing it safe for public approval.

It was just so where I wanted to go creatively. To me, the consistency in all my music has been the heart. I write like a singer-songwriter, which means 80 percent of the record is about culture. It’s not about love and just trying to be hooky. And writing a pop song that it isn’t about a relationship, it’s really hard. So writing “Intuition” was incredibly difficult, right? To write a pop hit that is about intuition and something really soulful.

The catch for me was what was happening in my personal life. It was during this album that I found out I was broke. It was during this album I found out I was three million dollars in debt. It was during this album I found out my mom wasn’t who I thought she was. Me taking this risk because I was like, “Oh, screw it. If it doesn’t work, it doesn’t work. I’m loaded.” It gives you a lot of courage. Scary when you’re three million dollars in debt.

I definitely took a long, hard pause in the middle of production to go, “Should I be doing this?” Like, “I need the money now.” I wanted to do it, I just couldn’t get off the track. It was just really what I wanted to do. So I did it. I think by this time too, like I started realizing it’s interesting that as a female you’re put in this box, that, “All right. Now you’re taken seriously. You’re smart, but you’re not allowed to be sexy. You better not be sexy.” And I was like, “Fuck you. I can be if I want.”

But one of the most memorable things to me about that time was I think it was [David] Geffen took me aside, he called me into his office. I didn’t work with Geffen; he wasn’t part of my label or my career. I obviously knew him from working with Joni Mitchell. I thought maybe he wanted me to write for somebody, like write for one of his artists. So I go in and the environment in the room was like I was in trouble. It was like I got called into the principal’s office. I don’t even know this guy and I feel like I’m in trouble.

I walk in, I pull up a chair, he pulls up a chair sitting almost knee-to-knee with me, and he gives a finger. He doesn’t say hi. He doesn’t say how are you, he doesn’t introduce himself. He got a finger out and he pointed at me and he said, “Nobody wants this generation’s Joni Mitchell to wear a mini skirt. You need to knock it the fuck off.”

Oh God.

JEWEL: That really strikes the chord. But yeah, it was an interesting album. I love that album. I love the writing on that album. I love the lyrics on that album. Like “Becoming” is incredibly poetic and you hear an “Intuition” acoustic, like that song stands up. So I love it. It just really pissed a lot of people off. But I daresay now, like Taylor Swift going into pop, I think that transition might have been easier for her. I don’t know.

Like, let’s say I wake up in the morning and you know me and we’re around each other. One morning, I’m going to wake up with sweatpants, one morning I might wear my pajamas till noon, one morning I might get on yoga pants, one morning I might get into a couture gown because I have an event to go to. You wouldn’t question my authenticity, right? You would go, “That makes sense. She’s in a different mood today. She’s doing something different today.” Music is the exact same. You’re talking about something that’s a reflection of my personal humanity over what I hope is 50, 60 years.

So I always found it so odd that the heart remains authentic, right? It’s always from a singer-songwriter’s perspective. It’s always lyric-driven. Then whether I dress it in a banjo or I dress it in an accordion or I dress it in cellos or I dress it in horn arrangements, it’s just dressing the heart. It’s so funny that it made people question [my] authenticity. When, to me, that was absurd. My authenticity is beyond reproach. That’s my, what do you call it? My currency is my authenticity. So I found it really funny that it scared people as if like a child almost, “Mommy’s dressed different today. Is it still mommy?” I thought it was so funny. Not to mention, I wrote every song on the album, right?

Also, I knew what I was up against. I knew it was going to be really hard. Again, I’ll go right back to this historical perspective of my goal has always been, “I want to be one of the best singer-songwriters.” Not one of the best females, I want to be one of the best, and that’s a lifelong ambition, a goal that I won’t know if I’ve achieved until I’m probably on my death bed. But when I looked at heroes for women that have pulled that off, there are not a lot of female singer-songwriters that have had the accolades or the credibility or the ticket power that Bob Dylan has had or Neil Young has had.

It’s still very hard even for males, right? There’s just not a lot of legendary singer-songwriters in general. But the women, like Joni, who’s every ounce as good as Dylan or Neil, doesn’t have the ticket power. [It’s] harder to age. They aren’t able to make the move that the men have made. Who knows why? The women that have had enduring iconic careers were always on top, right? Cher, Madonna come to mind. Whole different currency, whole different way of having a 50, 60-year career. Very valid, no looking down at it. It’s hard as fuck, that’s why nobody pulls it off, but it was always done through reinvention, and frankly contrivance a lot of the time.

Like when I think of Madonna, no offense, but I think of somebody who’s very smart, very strategic, and using that strategy to reinvent herself kind of from optics. That’s not how I work. I am not from optics. I’m from like the inside out, I’m from heart. But you have to realize, or what I realized, was the press has never seen a female do it from an authentic standpoint. They did get to see Dylan do it, right? And they were pissed, they hated that he went electric. You would’ve thought he killed somebody.

Neil fought really hard to be able to go from grunge to these Harvest-type records. But no female really had ever done as an authentic, real muse. So it was met with a lot of cynicism. It was met with like, “As if I was Madonna.” But again, that’s just where you make what you think is the right choice, and you have to play the long game, and you hope it comes out in the wash. You don’t get a guarantee of that. You still have to make the choice you think is right.

Jewel’s Freewheelin’ Woman is out 4/15 via Words Matter Music.

more from We've Got A File On You