The 1980s were defined by two unparalleled musical icons: Michael Jackson and Prince. Both artists revolutionized the industry, yet their dominance fueled an intense rivalry that was marked by competition, petty disputes, and even moments of outright hostility.

From the outset, their careers mirrored one another. Prince debuted with For You in 1978, while Jackson launched his solo career with Off the Wall in 1979. As 1999 dominated the charts, Jackson countered with Thriller, which in turn provoked Purple Rain. This back-and-forth wasn’t just limited to music sales—it extended to personal and professional interactions as well.

One of their first direct encounters came at a James Brown concert in 1983. Jackson took the stage, dazzling the crowd before suggesting Brown invite Prince up next. Unprepared, Prince attempted to play a malfunctioning guitar and then attempted to swing over the audience using a stage prop, only to crash into the crowd. Jackson reportedly mocked him endlessly, and according to Quincy Jones, Prince was so embarrassed that he later attempted to run over Jackson with his limo.

Their rivalry intensified in 1985 at the American Music Awards when Purple Rain bested Thriller for Favorite Pop/Rock Album. That same night, Prince was expected to participate in We Are the World, a charity single led by Jackson, but he refused, reportedly disliking the song. The following year, Jackson sought to collaborate with Prince on the song Bad, but Prince declined, objecting to the lyric, “Your butt is mine.”

The tension wasn’t just professional; it was deeply personal. At one point, Prince gifted Jackson a box of voodoo artifacts, making Jackson believe he was being cursed. Jackson, in turn, dismissed Prince as “rude and nasty,” expressing concern for his rival’s mental well-being.

Despite their animosity, Jackson continued to reach out, proposing collaborations even into the 2000s. In 2006, will.i.am arranged for Jackson to attend Prince’s Las Vegas show. Prince, knowing where Jackson was seated, deliberately performed directly in front of him in a seemingly taunting display. Jackson was reportedly upset, calling Prince “a big meanie.”

Though their rivalry never fully dissolved, Prince expressed regret after Jackson’s passing in 2009. In a 2010 interview, he reflected on their shared struggles with fame and religion, lamenting that they had never truly reconciled.

Their rivalry, though contentious, was fueled by mutual brilliance. While comparisons between the two were inevitable, both left an indelible mark on music history. Today, their legacy lives on—not as competitors, but as two of the greatest artists of all time.