Madonna's Ex Jenny Shimizu Felt 'Like a High Class Hooker' While Dating the Singer: 'So Crazy and Fun'

Mar. 15, 2025

Jenny Shimizu (left); Madonna (right).Photo:Rommel Demano/Getty; Jeff Kravitz/GettyJenny Shimizuwas having the time of her life in the ’90s.Not only was she living her truth as an openly gay model and enjoying professional success, but she was also having fun behind the scenes. In the new docuseriesIn Vogue: The 90s,the former Calvin Klein and Banana Republic model, now 57, opens up about her time romping around Europe with Madonna"I mean, you’re not gonna say no to Madonna in the ’90s," she recalls 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?’ ““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.”Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.Madonna (left) and Jenny Shimizu in 1993.Mediapunch/Shutterstock"My wife is going to kill me,” Shimizu joked in the docuseries, referring to wife Michelle Harper, whom she wed in 2014.Shimizu also touched on that time in her life in her memoir, released last year.‘It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy,” she wrote. “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.“The time the two spent together reportedly overlapped with Shimizu’s relationship with another big star —Angelina Jolie.Jolie reportedly toldGirlfriendsmagazine in 1997, perInStyle, that the model “could have been a deep love” for her.“I probably would have married Jenny Shimizu if I hadn’t married my husband,” she added, referring to her ex Jonny Lee Miller. “I fell in love with her the first second I saw her.““That time was so crazy and fun. There’s really something heartfelt about certain moments,” Shimizu adds in the docuseries, looking back at the first time she appeared on a campaign billboard in New York City.“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,” she says.“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. And I really am grateful to Calvin because he actually did something that was so positive globally.”In Vogue: The 90sis now streaming on Hulu.

Jenny Shimizu (left); Madonna (right).Photo:Rommel Demano/Getty; Jeff Kravitz/Getty

Rommel Demano/Getty; Jeff Kravitz/Getty

Jenny Shimizuwas having the time of her life in the ’90s.Not only was she living her truth as an openly gay model and enjoying professional success, but she was also having fun behind the scenes. In the new docuseriesIn Vogue: The 90s,the former Calvin Klein and Banana Republic model, now 57, opens up about her time romping around Europe with Madonna"I mean, you’re not gonna say no to Madonna in the ’90s,” she recalls 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?’ ““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.”Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.Madonna (left) and Jenny Shimizu in 1993.Mediapunch/Shutterstock"My wife is going to kill me,” Shimizu joked in the docuseries, referring to wife Michelle Harper, whom she wed in 2014.Shimizu also touched on that time in her life in her memoir, released last year.‘It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy,” she wrote. “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.“The time the two spent together reportedly overlapped with Shimizu’s relationship with another big star —Angelina Jolie.Jolie reportedly toldGirlfriendsmagazine in 1997, perInStyle, that the model “could have been a deep love” for her.“I probably would have married Jenny Shimizu if I hadn’t married my husband,” she added, referring to her ex Jonny Lee Miller. “I fell in love with her the first second I saw her.““That time was so crazy and fun. There’s really something heartfelt about certain moments,” Shimizu adds in the docuseries, looking back at the first time she appeared on a campaign billboard in New York City.“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,” she says.“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. And I really am grateful to Calvin because he actually did something that was so positive globally.”In Vogue: The 90sis now streaming on Hulu.

Jenny Shimizuwas having the time of her life in the ’90s.

Not only was she living her truth as an openly gay model and enjoying professional success, but she was also having fun behind the scenes. In the new docuseriesIn Vogue: The 90s,the former Calvin Klein and Banana Republic model, now 57, opens up about her time romping around Europe with Madonna

“I mean, you’re not gonna say no to Madonna in the ’90s,” she recalls 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?’ "

“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.”

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.

Madonna (left) and Jenny Shimizu in 1993.Mediapunch/Shutterstock

Mediapunch/Shutterstock

“My wife is going to kill me,” Shimizu joked in the docuseries, referring to wife Michelle Harper, whom she wed in 2014.

Shimizu also touched on that time in her life in her memoir, released last year.

‘It wasn’t about an emotional bond, it was about taking each other to the heights of sexual ecstasy,” she wrote. “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.”

The time the two spent together reportedly overlapped with Shimizu’s relationship with another big star —Angelina Jolie.

Jolie reportedly toldGirlfriendsmagazine in 1997, perInStyle, that the model “could have been a deep love” for her.

“I probably would have married Jenny Shimizu if I hadn’t married my husband,” she added, referring to her ex Jonny Lee Miller. “I fell in love with her the first second I saw her.”

“That time was so crazy and fun. There’s really something heartfelt about certain moments,” Shimizu adds in the docuseries, looking back at the first time she appeared on a campaign billboard in New York City.

“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,” she says.

“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. And I really am grateful to Calvin because he actually did something that was so positive globally.”

In Vogue: The 90sis now streaming on Hulu.

source: people.com