Madonna’s ex Jenny Shimizu recalls ‘crazy’ relationship with Queen of Pop

Angelina Jolie’s former girlfriend Jenny Shimizu has recalled her “crazy” relationship with Madonna in the 90s. 

Model Shimizu, best-known as one of the faces of CK One by Calvin Klein, spoke about her relationship with Madonna in docu-series In Vogue: The 90s.

“I mean, you’re not gonna say no to Madonna in the 90s,” she said. “It [was] great feeling like a high-class hooker. You’d get a phone call like: ‘Hey can you meet me at my Paris show’,” she claimed.

Shimizu, who was voted sexiest woman in a poll for The Pink Paper in 2005, continued: “So, I’d be like, ‘Yeah, I’m just finishing Prada. Right after Prada I’ll catch a plane over’. And I would. I’d go over to her hotel, to the Ritz, at like four in the morning, have sex, then fly back to Milan.”

Michelle Harper (L) and Jenny Shimzu attend W magazine's 40th anniversary dinner at the Gramercy Park Hotel.
Jenny Shimizu (R) married Michelle Harper in 2014. (Evan Falk/WWD/Penske Media via Getty Images)

Shimizu, who married Michelle Harper in 2014, joked: “My wife is going to kill me”, before adding of her first campaign billboard for Banana Republic above New York’s famous Times Square: “That time was so crazy and fun. There’s really something heartfelt about certain moments.” 

In 2007, Shimizu revealed that she had sexual relationships with Madonna and Girl, Interrupted star Jolie at the same time. 

She previously claimed that Madonna used her as a “sex slave”, adding: “I was her secret ‘booty call’, available any time of the day or night for secret sex sessions.”

Jolie has also been open about their relationship, telling Girlfriends magazine in 1997: “”I probably would have married Jenny Shimizu if I hadn’t married my husband [Jonny Lee Miller]. I fell in love with her the first second I saw her.”

In Vogue: The 90s is streaming on Hulu in the US.

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