Jenny Shimizu Spills On Her Wild ’90s Romps with Madonna

Jenny Shimizu lived life to the fullest in the ’90s. As a boundary-pushing model, she’d gone out into the world as an outspoken gay woman, causing ripples both on and off the catwalk. But behind all that glitz and glamour, Jenny’s private life was just as riveting-especially when it came to those trysts with Madonna.

In the new docuseries In Vogue: The ’90s, 57-year-old Jenny talks about her frenetic days as a Calvin Klein and Banana Republic model. She also spills all on her crazy exploits with the Queen of Pop herself. 

“I mean, you’re not gonna say no to Madonna in the ’90s,” Jenny said in the show’s final episode of recalling when Madonna called her as she jet-setted her way across Europe. 

“Not only was it great feeling like a high class hooker — because really it was. You’d get a phone call like, ‘Hey can you meet me at my Paris show. You’re in Europe right?’” Jenny added.

Jenny would hop on a flight, meet Madonna at her hotel at 4 a.m., and fly back to Milan after their rendezvous.

In her words: “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 4 in the morning, have sex, and then fly back to Milan.”

Those are light moments now, but she jokingly confesses her wife, Michelle Harper, perhaps may not like to know of all those. “My wife is going to kill me,” she playfully said, talking of Michelle whom she married in 2014.

Jenny also spoke about her love life in her memoir that came out last year. She penned a candid memoir about the time spent with Madonna: “‘It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy.”

“I loved the fact that I was at this woman’s beck and call. It turned me on, being ordered to her room whenever she felt like sex,” she said further. 

Jenny’s love life with Madonna reportedly ran parallel to her time with Angelina Jolie. In a 1997 interview with Girlfriends magazine, Angelina uttered the most famous words about Jenny: that she “could have been a deep love” and admitted, “I probably would have married Jenny if I hadn’t married my husband.” At that moment, Angelina was referring to her then-husband, Jonny Lee Miller.

“I fell in love with her the first second I saw her,” Angelina added. 

Meanwhile, Jenny’s career was taking off in a very groundbreaking manner. She remembers that one surreal moment of seeing herself for the first time on a billboard in Times Square. It was for a Banana Republic campaign, and below her image, the words “American Beauty” were written.

She was, after all, a Japanese American woman who had grown up confronting discrimination and whose parents had been interned. That moment’s resonance wasn’t lost on her.

“For “Being Japanese and having my parents going through internment camps, and being gay, and — to walk down the street and always get harassed in some way, for one second, seeing that campaign… it was such a, you know, it was a big statement,” she reflected, adding, “And I really am grateful to Calvin because he actually did something that was so positive globally.”