A High-Class Escort The Midtown Times —The '90s were a whirlwind for Jenny Shimizu, the renowned model who entangled with one of the biggest pop stars of the era, Madonna. In the newly released docuseries "In Vogue: The 90s," Shimizu, now 57, revisits her memorable experiences, including an electrifying relationship with the global icon. At …
Former Supermodel Jenny Shimizu Reflects on Wild Days with Madonna: ‘Like a High-Class Escort’
The Midtown Times
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A High-Class Escort
The Midtown Times —The ’90s were a whirlwind for Jenny Shimizu, the renowned model who entangled with one of the biggest pop stars of the era, Madonna. In the newly released docuseries “In Vogue: The 90s,” Shimizu, now 57, revisits her memorable experiences, including an electrifying relationship with the global icon.
At the height of her modeling career, representing brands like Calvin Klein and Banana Republic, Shimizu reveled in the adventurous nature of her fling with Madonna. “You couldn’t turn down Madonna in the ’90s,” she reflects in the final episode of the series. Shimizu humorously recalled feeling like “a high-class escort,” often summoned to accompany the singer at a moment’s notice. “I’d get a call saying, ‘Hey, meet me at my show in Paris, you’re in Europe, right?’” she shared. “I’d be wrapping up a show with Prada, then catch a flight straight to her hotel for a rendezvous.”
Shimizu, who is now married to Michelle Harper, looked back on the affair with humor, joking, “My wife is going to kill me,” when recalling those wild days. Her relationship with Madonna wasn’t based on deep emotional connections, as she revealed in her memoir last year, but rather on intense sexual encounters. “I loved being at her beck and call. It was thrilling,” she wrote.
Shimizu’s time with Madonna she has coincided with her much-publicized romance with another Hollywood A-lister, Angelina Jolie. Jolie once told “Girlfriends” magazine in 1997 that Shimizu could have been “a deep love,” admitting she might have married Shimizu if not for her then-husband, Jonny Lee Miller.
Beyond the headlines about her star-studded relationships, Shimizu also shared how deeply personal her modeling career was. Appearing on a campaign billboard in Times Square for Banana Republic was a milestone moment for her. “For someone who’s Japanese-American, whose family went through internment, and who was openly gay, to see ‘American Beauty’ under my photo—it was powerful,” Shimizu recalled. “It was a global statement, and I’m grateful to Calvin [Klein] for that.”
In this poignant reflection, Shimizu celebrates her wild and fulfilling journey through fame, fashion, and relationships, cementing her legacy as a model and an icon of a transformative era.
The Midtown Times is committed to delivering accurate, timely, and comprehensive news to our readers.
