The Foolish Games hitmaker recently released a new memoir, titled Never Broken, in which she details an unlikely relationship with the Oscar winner when she was just starting out in Hollywood.
On the heels of her debut album in 1995, Jewel appeared on comedian Conan O'Brien's late night talk show and caught the attention of Penn, who had separated from then-girlfriend Robin Wright earlier that year (95).
In her tome, she writes, "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."
Jewel goes on to say that she wrote a song called Emily for the movie, and after that, the two struck up a secret romance.
She writes, "We spoke on the phone a lot and he was a fantastic flirt and I did not mind one bit. 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.
"I moved very slowly with him but he was a persistent and inventive suitor, and I enjoyed it immensely. I kept our burgeoning relationship very quiet."
While they were together, Jewel also asked Penn to cut out all alcohol and drugs from his life, writing, "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 soundcheck, he responded with a melancholy stare and then canary-eating grin and said it would be impossible not to fall in love with me. I looked at him to see if he was serious. It seemed he was... I enjoyed Sean and would eventually fall in love."
Jewel also describes intimate moments they shared undercover at the Venice Film Festival and in France, but after a few months, their relationship fizzled out, and they split that same year (95).
Penn reunited with Wright, the mother of his two young kids with, and they wed in 1996. The actors finalised their divorce in 2010. He recently split from longtime girlfriend Charlize Theron.
Jewel filed for divorce from her rodeo cowboy husband Ty Murray last year (14).