“You Don’t Say No To Madonna:” Model Jenny Shimizu Reflects On Their Wild ’90s Romance

“I felt like a high-class hooker,” said Jenny Shimizu, a former model for Calvin Klein and Banana Republic, reminiscing about her whirlwind romance with pop icon Madonna during the ’90s.

The testimony comes as part of Disney’s docuseries In Vogue: The 90s where, in its final episode, the now 57-year-old reflected on the exhilarating time she spent traveling across Europe with the superstar.

“I mean, you’re not gonna say no to Madonna in the ’90s,” Shimizu recalled, explaining how she used to get calls out of nowhere from the singer, who would fly her no matter where she was in the world to her hotels for intimate, one-night encounters.

Far from feeling demeaned by being treated as an escort, the former model relished in the dynamic. 

“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 it.”

Asian-American model Jenny Shimizu confessed to have felt like “high-class hooker” during her relationship with Madonna in the 90s

Image credits: Mediapunch / Shutterstock / Vida Press

Jenny Lynn Shimizu, born in 1967 in San Jose, California, has always led an openly gay life. The 2001 book Bad and Beautiful: Inside the Dazzling and Deadly World of Supermodels details how she was discovered by Calvin Klein while working as a mechanic.

Her androgynous looks became the trademark of her career, with her breakout campaign being for Banana Republic’s American Beauty collection. Prada soon hired the model and turned her into the first Asian to model for its catwalk, opening the show in 1994.

Image credits: Penske Media / Getty

In 2005, Shimizu became part of the judging panel for Tyra Banks’ reality show America’s Next Top Model, as well as Bravo TV’s Make Me a Supermodel.

Shimizu would marry fashion entrepreneur Michelle Harper in 2014. The pair met a New York party in 2012, and keep a healthy relationship to this day.

Shimizu was also known to have had an affair with actress Angelina Jolie in 1997, with the former stating that the they shared a “deep love”

 

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Madonna wasn’t the only high-profile fling that the model had during her career, as Angelina Jolie revealed in a 1997 interview that she had fallen “in love with her the first second [she] saw her,” after they shared the set of Foxfire, a 1996 an American teen drama film.

Image credits: Sonia Moskowitz / Getty

“I would probably have married Jenny if I hadn’t married my husband,” she confessed, making a reference to Jonny Lee Miller, a british actor whom she had married a year earlier in 1996, and separated from during that year.

The couple divorced in 1999, but it’s unclear whether Jolie’s affair with the model had anything to do with the decision.

 

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The model recently participated in the latest edition of the famous Pirelli calendar, an annual publication dating back to 1964.

The 2025 photo collection is expected to release later this year, and will feature models such as Hunter Schafer, Padma Lakshmi and Mugler Muse.

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