Jewel: I Dated, Fell in Love With Sean Penn During His Separation From Robin Wright

jewel and Sean Penn
Jewel revealed in her new memoir, Never Broken, that she dated and fell in love with Sean Penn in the '90s, while he was on a break from Robin Wright. Jennifer Lourie/Getty Images; Jeff Kravitz/FilmMagic)

Now this is a gem of a celebrity memoir. In Jewel’s new book, Never Broken, the “Foolish Games” singer-songwriter, 41, writes that she fell in love with Sean Penn in the mid-’90s, during his brief break from his future second wife, Robin Wright.

In the tome, she recalls when her music career was in its beginning stages. “Around this time, in 1995, I got my first TV break,” she writes of her television debut on Conan O’Brien‘s show. “I think I was wearing purple polyester pants with a black T-shirt and a tacky belt with a rainbow buckle that I loved. The performance was a huge break for me.”

The singer’s debut album, Pieces of You (which included her smash single, “Who Will Save Your Soul”), was released that same year, and went on become one of the highest-selling breakout records of all time.

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Jewel then briefly returned home to Alaska, when her father, Atz Kilcher of Discovery’s Alaska: The Last Frontier, received an odd phone call at his home. “One day my dad came to find me, saying ‘Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn,'” she writes. “‘No sh–,’ I said, chuckling. ‘What did you do?'”

Her dad said he hung up on the person — only to answer the call again. It really was Sean Penn. “He had seen me on Conan and was working on a movie he’d written called The Crossing Guard. He wanted me to compose a song for it. I told him I would and he said he would meet me anywhere to screen the movie, I could name the day. I gave him my cell number and figured I would never hear from him again.”

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Instead, they secretly fell in love. The stars first met at a salon in San Diego, where Jewel was getting her hair cut. Jewel ended up writing a song called “Emily” for Penn’s 1995 flick, as planned, and their romance followed. “We spoke on the phone a lot and he was a fantastic flirt and I did not mind one bit,” she shares. “But I was no fool and knew I was most likely a trifle to him. I intended to give him no such conquest. I put that man through his paces and he took it in stride. He began to court me in earnest, following me around on tour, acting as my de facto roadie.”

Jewel recalled how they would discuss books, and art, and that the two-time Oscar winner, now 55, “sincerely believed” in her music. (Penn, of course, was married to another music superstar, Madonna, from 1985 to 1989.) “I moved very slowly with him but he was a persistent and inventive suitor, and I enjoyed it immensely,” she recalls in her book. “I kept our burgeoning relationship very quiet.”

She also asked him to be completely sober. “I liked his mind sober, and had fun playing this way. When I told him this in all seriousness, in a dive bar after a sound check, he responded with a melancholy stare and then canary-eating grin and said it would be impossible not to fall in love with me,” she continues. “I looked at him to see if he was serious. It seemed he was.”

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The two then went on the down-low to the Venice Film Festival together, which Jewel discusses in great detail including an epic Jack Nicholson encounter. “Sean would whisper in my ear and explain everyone’s backstory to me. It was not my world and I was pretty sure it never would be. Sean took me to see the sights in Montartre and wrote me in notes that he hid in my pockets,” she reveals. “…I enjoyed Sean and would eventually fall in love.”

As the narrative goes, the under-the-radar pair split that same year. Penn — who had fathered two kids, Hopper and Dylan, with Forrest Gump actress Robin Wright — got back together with the House of Cards actress, and they married in 1996. Wright and Penn finalized their divorce in 2010.

sean penn and robin
Robin Wright and Sean Penn attend the “Forrest Gump” Hollywood Premiere on June 23, 1994 Ron Galella, Ltd./WireImage

Jewel eventually married cowboy Ty Murray in 2008, from whom she eventually filed for divorce in 2014. They share share one son, Kase, 4.

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On Monday, the songstress opened up to Howard Stern about her split from Penn. “It was hard on me. He really believed in me at a time when nobody else did,” she recalled. “And he really made me feel good about myself and I was so desperate for that. Having that go away was hard.”

Meanwhile, Penn made headlines on Tuesday, Sept. 22, after filing a $10 million defamation lawsuit against Lee Daniels for indirectly linking him to domestic abuse. One portion of Penn’s suit referred to another one of his famous exes. “Penn (unlike Howard) has never been arrested, much less convicted, for domestic violence,” the suit obtained by Us Weekly reads. “As his ex-wives (including Madonna) would confirm and attest.”

For more details from Jewel’s life, pick up a copy of her memoir, Jewel — Never Broken: Songs Are Only Half the Story, available now.

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