Behind The Music: Michael Jackson’s ‘Dirty Diana’

Released in 1988 as the final single from Michael Jackson’s Bad album, “Dirty Diana” marked a turning point in Jackson’s career, blending his pop roots with a darker, more rock-infused sound. This powerful track, both musically and thematically, would become one of the most iconic songs in pop history, capturing Jackson’s internal battle against the temptations of fame, lust, and the dangers that came with it.

The inspiration behind “Dirty Diana” stems from a blend of Michael Jackson’s real-life experiences and the influence of contemporaries like Prince. After the monumental success of Thriller, Jackson sought to expand his musical horizons by embracing the rock genre, a theme pioneered by his rival-turned-peer, Prince. The release of Purple Rain in 1984, with its blend of rock, psychedelia, and darkly explicit tracks like “Darling Nikki,” caught Jackson’s attention. The raw, unfiltered honesty of Prince’s work was a bold statement in pop music, and Jackson, in his own way, wanted to explore this edgier, more dangerous side of fame.

“Dirty Diana” tells the story of a persistent, seductive woman—an archetype of the professional groupie—who refuses to take no for an answer. Diana’s pursuit of Jackson becomes more than just a fleeting temptation; it’s a representation of the dangerous allure of celebrity. Jackson portrays himself as a man caught between desire and the responsibility to stay true to his own values, an internal struggle that had long been part of his life as a global icon. As Jackson explained in interviews, the song was inspired by women he encountered throughout his career—those who would do anything to be close to the famous musicians they idolized.

The production of the track is just as compelling as its lyrics. Recorded in 1986, “Dirty Diana” required an authentic rock edge, and Michael Jackson turned to a familiar collaborator for the intense guitar riff: Steve Stevens, guitarist for Billy Idol. Stevens brought a heavier, raw sound to the track, which was far darker than anything Jackson had previously explored. He described the experience of working on the song as “great,” as it allowed him to dig into the heavier side of rock. The result was a powerful track that blended Jackson’s smooth pop style with the grit of rock, creating a sound that was both polished and ferocious.

The music video for “Dirty Diana,” directed by Joe Pytka, was a spectacle in itself. Filmed in Long Beach, Los Angeles, it featured Jackson performing the track in a raw, live performance setting. The video’s most memorable aspect was the casting of Lisa Dean, who played the titular Diana. Chosen for her striking beauty and model-worthy legs, Dean embodied the character of the “ultimate woman” who lures Jackson into a web of temptation. Despite the video’s overt sensuality, Jackson’s portrayal of Diana remained free of romantic interest. Instead, he maintained an air of professionalism, focusing more on his performance than on any personal connection with the actress. The resulting image was one of mystery and allure, where less was often more.

Upon its release, “Dirty Diana” would go on to make history. It peaked at number one on the Billboard Hot 100, making Michael Jackson the first artist ever to have five number-one hits from one album. The success of the song solidified Jackson’s place in pop culture and further cemented his reputation as the King of Pop. However, despite its commercial triumph, “Dirty Diana” was not without its controversy. Critics described the song as deeply misogynistic, with its portrayal of a manipulative woman challenging Jackson’s “good guy” image. Some even speculated that the song was aimed at his longtime friend, Diana Ross, a claim Jackson denied, asserting that “Dirty Diana” was based on a composite of real-life experiences with groupies.

Interestingly, Jackson would later go on to perform “Dirty Diana” during his Bad World Tour, but notably removed it from the setlist for a performance at London’s Wembley Stadium in 1988, when he found out that Princess Diana would be in attendance. In a gesture of respect for the royal, Jackson took the song out of the show, later recounting that the princess had expressed interest in hearing it. Jackson’s consideration of the princess’s feelings showed a level of sensitivity and awareness that contrasted with the darker, more provocative themes of the song itself.

Despite mixed reviews, “Dirty Diana” remains one of Michael Jackson’s most captivating songs, blending the worlds of rock and pop while tackling themes of temptation, fame, and the darker side of celebrity. It showcased a side of Jackson that the public rarely saw, a more vulnerable yet defiant artist, grappling with the pressures of fame and the complicated relationships that came with it. As one of the defining tracks of the Bad era, “Dirty Diana” is a testament to Jackson’s ability to evolve, take risks, and push boundaries—both musically and personally—solidifying his place as one of the greatest artists in history.