There’s a moment in George Michael’s music video for “Freedom! ’90” where director David Fincher’s camera zooms in on a leather jacket hanging in a closet. It’s the piece Michael sported proudly three years earlier in the music video for “Faith” — the item that helped Michael reinvent himself from the squeaky-clean teen idol in Wham! into a bad-ass sex god of the 1980s. But with “Freedom! ’90,” Michael sought to overhaul his image once again. And a few moments later, that leather jacket spontaneously combusts; ditto the “Faith” video’s Wurlitzer jukebox and his Gretsch guitar. Goodbye to all that.

“They were horrified,” Michael recalled of his label Sony’s reaction, in an MTV interview in 2004. “Why would you burn something that made Sony $150 million dollars? But I quite enjoyed it.”

It might be hard to imagine now, but when George Michael’s “Freedom! ’90” music video was released in 1990, it was nothing short of revolutionary. Its creator, who was embroiled in a dispute with his label, Sony, over his refusal to heavily promote his album Listen Without Prejudice Vol. 1, chose not to star in his own music video. Instead, he scored a cast of lip-synching supermodels — Naomi Campbell, Cindy Crawford, Linda Evangelista, Tatjana Patitz, Christy Turlington, plus a crew of male models — who vamped gorgeously in a dark and dingy space. And for a Grammy-winning artist who was shaped into a global pop star thanks to MTV, Michael was slyly flipping off the network that helped make him a star.

“George was thumbing his nose at MTV with the video,” producer Simon Straker told EW in 1991.

But once it hit airwaves, “Freedom! ’90” went into heavy rotation on the cable channel, scored five MTV Video Music Awards nominations (it won zero), became one of the most memorable videos of the last two-and-a-half decades, and served as a rallying anthem for the LGBT movement. It was such a classic, in fact, that Michael himself tried to recapture some of that supermodel magic for his 1992 single “Too Funky.”

“One of my better ideas was getting five gorgeous supermodels [miming to the song] that people still want to look at today,” Michael said in an interview at the time, according to the biography Careless Whispers. “If you’re going to say to your record company, ‘Look, I’m not going to be in this video,’ I’d say that’s a fairly good consolation prize really, you know, those five gorgeous babes.”

While Michael chose not to get in front the camera, he was heavily involved in its creative execution. The inspiration for supermodel stars came after Michael saw a portrait of the women shot by Peter Lindbergh for the January 1990 cover of British Vogue. And he hired director David Fincher, who’d had success helming Madonna’s “Express Yourself” video, and top stylist Camilla Nickerson. The team holed up on a London soundstage for several days. “They were long days,” Turlington told Harper’s Bazaar. “I don’t recall any specific direction from David Fincher. He was focused on the lighting I recall. George was there the whole time and very involved.”

As Nickerson told Allure in a definitive history of the video, “It was epic. It had a grandeur and a Blade Runner feel.”

Michael was friendly with his model cast prior to shooting, but they didn’t know what they were getting themselves into upon arriving on set. Evangelista reportedly had to be convinced to participate. And Michael had sent his stars music to learn just days before production began. Turlington recalled to Bazaar that each model largely shot her parts separately. And the scenes were somewhat uncomfortable. “I do remember feeling a little bit like, ‘Oh, why did I get stuck in the tub? I want the big glamour-puss hair. I want to be wearing the heels or blowing cool smoke rings, like Tatjana,” Crawford told Allure. “But if you were working with good people, you just did what they asked.”

Off-camera, however, the vibe on-set was jovial among cast and crew. “We’d drink red wine and sing songs in the evening because it kind of went on late,” hair stylist Guido told Allure. “And George was just like one of the gang, in the trailers, hanging out.”

“Freedom! ’90” would go on to become one of Michael’s signature songs — he performed it at the closing ceremony of the 2012 Olympics — and the video remains a defining moment in MTV’s history. As for Michael bidding farewell to his past as an ’80s pop icon and embracing an uncertain future at the dawn of a new decade, he felt vindicated: “I thought that was a wonderful way to get rid of the image, really… I felt that way,” he told MTV in 2004. “I wanted to get rid of that. I felt like I’d cornered myself again.”