Madonna’s ex Jenny Shimizu jokes she felt like a ‘high class hooker’ while flying across Europe for their late-night liaisons as she gives rare insight into their ‘crazy and heartfelt’ romance

Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance

As a lifestyle expert with decades of experience under my belt, I find myself captivated by the tales of the stars that defined the 90s, as portrayed in the Disney+ documentary “In Vogue: The 90s”. Jenny Shimizu‘s account of her relationships with both Madonna and Angelina Jolie is a testament to the era’s vibrant energy and the complexities of stardom.


During the peak of their passionate relationship, Madonna’s former girlfriend, Jenny Shimizu, humorously stated that she often felt like a sophisticated escort.

57-year-old model shares unique perspectives on her bond with the 66-year-old singer in the documentary ‘In Vogue: The 90s’, available on Disney+. This film revisits the celebrities who shaped an unforgettable era in the magazine’s history.

In the closing episode of the series, Jenny disclosed that she had a romantic involvement with Madonna while simultaneously dating Angelina Jolie, openly stating that she would travel through Europe for clandestine trysts with the famous figure at night.

In 2014, the actress mentioned that she traveled from Milan to Paris to spend a night with Madonna on one particular instance. Afterward, she hurriedly returned to Italy for her upcoming performance. Later, she also revealed that she is married to Michelle Harper.

She said: ‘I mean you are not going to say no to Madonna in the 90s. 

Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance

Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance

‘It felt fantastic to experience the luxury of being mistaken for a high-class model, which it truly was. I would often receive invitations like, ‘Meet me at your show in Paris, since you’re in Europe, aren’t you?’ To which I would casually respond, ‘I’m wrapping up work at Prada now, I can hop on a flight.”

‘And I would go to the Ritz at four in the morning and have sex and fly back to Milan.’

In 2014, Jenny tied the knot with her spouse Michelle Harper. Prior to this, she had shared the story of her romantic involvement with Madonna in her 2023 memoir. She wrote that their bond transcended mere physical attraction, delving into a profound emotional connection.

She expressed earlier: ‘It wasn’t a matter of emotional attachment, it was about reaching the pinnacles of sexual bliss together. I enjoyed being under her control. The thrill of being summoned to her room whenever she desired intimacy appealed to me.’

This model gained significant recognition following her engagement with Calvin Klein for modeling assignments. Moreover, she became the trailblazer as the first Asian model on the Prada runway, and also made history by being the first ethnic minority model to kick off the show.

Simultaneously, both Jenny and Madonna were romantically engaged, yet she was also entangled in a romantic relationship with her fellow Foxfire cast member, Angelina Jolie.

In a 1997 interview, Angelina openly admitted about their romance by stating: ‘From the moment I laid eyes on her, I felt an instant connection. If not for my current marriage to Jonny Lee Miller, I might have wed Jenny.’

In the documentary, Jenny shared insights about her journey to fame in the fashion world, commenting: ‘I can just imagine my wife’s reaction, but those days were wild, thrilling, and there was a genuine emotional depth to some of the experiences.’

Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance
Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance
Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' while flying across Europe for their late-night liaisons as she gives rare insight into their 'crazy and heartfelt' romance

One time, my pals took me to Times Square, and they exclaimed, “Check this out!” It so happened that I had recently completed a Banana Republic ad campaign, and beneath it was written “American Beauty.

For the first time in my life, I’ve never been referred to as an American or a beauty. Despite being Japanese, gay, and often faced with harassment while walking down the street, seeing that campaign from Calvin Klein was incredibly powerful for me. It was a significant statement, and I’m thankful to Calvin Klein for creating something so positive.

The documentary In Vogue: The 90s is a star-studded look at the fashion industry during the decade.

Communicates with ex-Vogue editors like Edward Enninful, and celebrities such as the supermodel Naomi Campbell, actress Gwyneth Paltrow, and Sarah Jessica Parker from Sex and the City.

The documentary additionally highlights exceptional, unseen-before records from influential figures within the field, bringing to light the unspoken tale of the era’s iconic pop culture instances and trends.

Additional participants will encompass fashion designers such as Tom Ford, Marc Jacobs, and Jean Paul Gaultier, actress Claire Danes, models Amber Valletta and Tyson Beckford, filmmaker Baz Luhrmann, and former U.S. political figure Hillary Clinton.

Currently, Madonna is dating Akeem Morris, a 28-year-old Jamaican football player, making this another addition to her extensive collection of romantic relationships.

In 2022, it seemed like they had their initial encounter, as he graced the cover of her August 2022 edition for Paper Magazine.

Starting this coming Friday, September 20th, you’ll have the chance to stream the last three episodes of the series “In Vogue: The 90s” on Disney+.

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2024-09-17 18:09

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