In 1991, the red carpet at the 63rd Academy Awards was lit not just by film stars, but by two of the most iconic figures in music history — Madonna and Michael Jackson. Their surprise appearance together, walking hand-in-hand, instantly made headlines and set off a media frenzy. It was their first official date, and it marked the beginning of what would become a short-lived romance and an ultimately failed musical collaboration.

Before that fateful Oscars night, the two had only crossed paths once — back in 1984, when Madonna attended Jackson’s Victory Tour at Madison Square Garden. At the time, Jackson was already a global sensation, while Madonna was still emerging. She admired Jackson deeply, even hiring his manager, Freddy DeMann, in hopes of mirroring his success. That same year, she expressed admiration for Jackson in an interview, even incorporating “Billie Jean” into her own performances.

By 1991, Madonna’s fame had skyrocketed, making her one of the few artists whose star power could match Jackson’s. As Jackson worked on his Dangerous album, he saw an opportunity to team up with Madonna — combining their talents and media magnetism. He reached out, and the two arranged a dinner date at the Los Angeles hotspot “The Ivy.” The paparazzi swarmed, and during dinner, the upcoming Academy Awards came up. Madonna, recently single after her split with Warren Beatty, asked Jackson to attend with her — and he agreed.

The pair stunned the world on Oscar night. Madonna paid homage to Marilyn Monroe, wearing a glittering Bob Mackie gown, white opera gloves, and $20 million in Harry Winston diamonds. Jackson matched her glamour with a sequined blazer, gold belt, and signature flair. After the ceremony, they appeared together at Spago’s for the afterparty, although Madonna reportedly spent much of the night with Beatty. Jackson was left alone until Diana Ross came to his rescue.

In interviews years later, Madonna confirmed she made the first move and kissed Jackson. She admitted he was shy and needed a little encouragement — and even a glass of chardonnay. Rumors swirled that she spent the night at Neverland Ranch, but things quickly soured. Madonna reportedly refused to go to Disneyland, Jackson’s favorite place, jokingly calling it a deal-breaker.

The two also attempted to collaborate musically. Jackson offered Madonna the chance to co-write a song titled “In the Closet.” She contributed lyrics and pitched a provocative concept — both appearing in drag in the music video. Jackson rejected the idea, and Madonna walked away from the project, calling it a “silly love song.” Jackson ended up recording the track with Princess Stéphanie of Monaco instead, using a much tamer concept than Madonna had envisioned.

The relationship took a further turn for the worse when Madonna began publicly criticizing Jackson. In a 1991 interview, she said she wanted to revamp his image — cutting his hair and removing his iconic buckles. Jackson, deeply offended, was reportedly “mad as hell.” He criticized Madonna in the unauthorized biography The Magic and the Madness, saying she couldn’t sing or dance and was only skilled at marketing herself.

In a taped conversation with spiritual advisor Shmuley Boteach, Jackson claimed Madonna was rude to children and not a nice person. In another account, during a restaurant encounter, Madonna allegedly snatched Jackson’s sunglasses and broke them, saying, “Tonight, you’re gonna be normal like the rest of us.”

Despite the fallout, Madonna occasionally defended Jackson. In 2003, she criticized the Living with Michael Jackson documentary as “exploitative” and “unfair.” After Jackson’s death in 2009, she paid tribute during her Sticky & Sweet Tour, performing “Billie Jean” and “Wanna Be Startin’ Somethin’.” She later shared a throwback photo of their Oscar night, calling it the “Best Date Ever.”

In 2019, Madonna defended Jackson again amid the Leaving Neverland allegations. “People are innocent until proven guilty,” she said, emphasizing her own experience with false accusations and calling for fairness.

Though their romantic and musical union never materialized, the brief connection between Madonna and Michael Jackson remains one of pop culture’s most fascinating “what ifs.” Their date may have been legendary, but their relationship was anything but a fairy tale.