And while the arrest threats in Canada, beef with the Pope and relationship drama with Warren Beatty are now legendary, nothing in the film is as famous as the shocking game of truth or dare the pop icon and her backup dancers play at the dinner table.
PEOPLE caught up with six of Madonna's Blond Ambition dancers, who are the focus of the new Dutch documentary Strike a Pose, premiering at the Tribeca Film Festival on Friday.
Salim "Slam" Gauwloos knows just how groundbreaking the on-camera kiss he shared with fellow dancer Gabriel Trupin really was.
When Luis Camacho, another member of Madonna's troupe, dared him to French-kiss Trupin, Gauwloos all but leapt from his seat and crossed the table for a passion round of PDA, as the pop star and other dancers hooted and hollered in approval.
Check out the iconic pop culture moment in the clip below, at the 1:06 mark. (DISCLAIMER: The video footage features mature content.)
"At that point, I was a little nervous because I was in a relationship," Gauwloos recalls. "I was like, 'Oh my God...'"
Adds Jose Gutierez, who was also on the Blond Ambition tour and who PEOPLE interviewed with Gauwloos: "He had a boyfriend at the time! And so did Gabriel! But you guys wanted it to happen. And Madonna wanted to see it so bad – she always wanted to see it."
But, what Gauwloos was even more worried about was exposing his sexuality so forthrightly.
"It was so early – 1990? Being out of the closet, it could have been hard to get more work, so I was a little nervous about that," he says. "But it inspired people."
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With Strike a Pose, filmmakers Reijer Zwaan and Ester Gould give an in-depth look at the dancers' lives now and what life events they've overcome. And at the end of the film, all six of the remaining dancers (Trupin died in 1995 of AIDS) reunite for the first time in over a decade.
At their reunion dinner, they, fittingly, play another game of truth or dare.
But this time, "I was like, 'I'm not kissing anybody!'" says Gauwloos. Feigning exasperation, he adds of attending the film's world premiere, which featured footage of the kiss, in Berlin: "I was there with my husband, and the kiss! The kiss! The kiss again?!"
Still, 26 years later, he has no regrets.
"We were being gay when it was not cool," he says, adding jokingly: "Now everybody's gay."