02/08/2013 02:28 pm ET Updated Feb 08, 2013

Jewel Talks 'Greatest Hits' Album, Homelessness, And The $39.99 Sundress That Redefined Her Life

At 38, Jewel has plenty of life experience to draw from. But the four-time Grammy award nominee still remembers a time when she was just a struggling teenager, convinced she "was going to end up in [her] car again."

Performing in New York City on Tuesday to celebrate the release of her new "Greatest Hits" album, Jewel showcased a vulnerable side, detailing to the audience how she ended up homeless after turning down a record producer's demands for sex. But, in an interview with The Huffington Post before the show, she also revealed just how determined she can be. "I can move every muscle in my face," she said. "I just remember, like in 4th grade science class, they said your muscles in your face were involuntary. And it just pissed me off. I was like ‘they’re my muscles. Bullshit! They’re my bitch. I’m gonna dominate!’"

Jewel is not afraid to wear her stories on her sleeve, and perhaps it's that conscious honesty and authenticity that has helped her to continue to find paying work despite the fact that it has been almost two decades since her most successful album went platinum 15 times over. She hosted "Nashville Star," a country music television competition, and appeared as a guest judge on the Season 6 premiere of "American Idol." "It’s very repetitive for the judges, so it’s hard for you to stay fresh," the singer told The Huffington Post. "You actually have people’s lives and hopes and dreams in your hand. I think that’s why I like 'The Voice' -- the mentoring. I think that’s what makes that show really great. The panelists are looking at the talent from the viewpoint of an artist, not just a record person, not just like mercenary pop, like 'What’s going to be a hit?'"

Jewel takes the mentoring thing seriously, even when it comes to her fellow pop stars. Case in point: for the new album, she re-recorded her 1997 hit "Foolish Games" with "American Idol" winner Kelly Clarkson. "I guess she had sung the song in several talent shows growing up," Jewel shared. "It’s neat to be able to influence artists that I really like."

She can even claim to have held sway over America's reigning country-pop goddess. "Me and Taylor Swift had a gig together years ago, and her mom was like, 'She listened to your record a bunch when she was a kid.' It’s neat."

So, how was it singing with Clarkson? "She’s kind of a freak of nature vocally. I go in there and I was holding to this long note, holding the melody, and it’s as high as I can sing and I’m like on my tippy toes trying to reach it and she goes in there and she just nails the harmony, above it, in full chest voice. I mean, it’s like watching a thoroughbred run. It isn’t right."

During Tuesday's concert, which was sponsored by iHeartRadio, she recalled a different kind of humbling experience: hearing her song "Hands" on the radio in the wake of 9/11, a song that chronicles her struggles to maintain control in an industry that requires painstaking perseverance.

Jewel's hands are unusually small -- they measure in at 5.25 inches, about an inch and a half below average -- but that's not what the song is about. It's really about what she used to do with those hands, and why she decided to stop. "I had taken to shoplifting, and it started with carrots, which are apparently the gateway vegetable because they led to the hard stuff, like peanut butter," she said. "And then one day I wanted a sundress, so it looked like I was gonna escalate. I was standing there thinking about stealing it and I saw the tab and it was like $39.99 and I thought 'When did I lose faith in myself? When did I stop thinking I could earn $40?' And I didn’t steal the dress. I didn’t steal anything again. I just wrote these lyrics about how nobody owes you anything."



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