Why Madonna's Ex Jenny Shimizu Felt 'Like a High Class Hooker' While Dating Pop Icon

Jenny Shimizu is looking back at life in the '90s. The openly gay model not only was living it up on the runway, she was having the time of her life behind the scenes too. In the new docuseries In Vogue: The 90s, the former Calvin Klein and Banana Republic model opens up about her time traveling around Europe with Madonna. "I mean, you're not gonna say no to Madonna in the '90s," Shimizu, now 57, recalled in the final installment of the six-episode series. "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?'" She 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 4 in the morning, have sex, and then fly back to Milan." "My wife is going to kill me," Shimizu joked in the doc, referring to wife Michelle Harper, to whom she tied the knot in 2014. She also reflected on that time in her life in her 2023 memoir, spilling on the physical relationship she had with the now 66-year-old music icon. "It wasn't about an emotional bond, it was about taking each other to the heights of sexual ecstasy," she wrote of her brief love affair with the "Vogue" singer. "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." Shimizu's time with Madonna reportedly overlapped with her relationship with another A-lister -- Angelina Jolie. Back in 1997, per InStyle, Jolie told Girlfriends magazine that Shimizu "could have been a deep love" for her. "I probably would have married Jenny Shimizu if I hadn't married my husband," Jolie reportedly said at the time, referring to her ex Jonny Lee Miller. "I fell in love with her the first second I saw her." Touching on her modeling career, Shimizu described the era as "crazy and fun." Looking back at the first time she appeared on a campaign billboard in New York City, she added, "I remember my friends bought me to Times Square and said 'Look!' And I had just done a Banana Republic campaign. And underneath it said, 'American Beauty,' and never in my life had I been described as American or as a beauty." "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," Shimizu continued. "And I really am grateful to Calvin because he actually did something that was so positive globally." In Vogue: The 90s is now streaming on Hulu.