(Credit: Alamy)
Thu 15 January 2026 0:00, UK
When she was at her pop peak across the 1980s and ‘90s, Madonna stood in the cultural landscape as a virtual institution unto her own.
Punk burnished Madonna’s spiky spirit. At the start of the decade, when a young Madonna Louise Ciccone was a hungry dancer and two-bit rock drummer, the potent melting pot that descended upon New York’s East Village of mutant disco, new wave edge, and the seamier ends of the dance underground all instilled in Madonna a healthy instinct for pushing boundaries and subverting sexual mores.
Such intuition would serve her more than well. Bagging a deal with Sire and surrounding herself with the right producers with access to the latest LinnDrum drum machines and Oberheim OB-X synthesisers, Madonna would marry her striking electro-disco sound with a keen visual identity ready-made for MTV’s eager promo mill.
Before long, Madonna exploded as one of the era’s veritable chart icons, enjoying the Queen of Pop crown securely as the 21st century arrived.
Yet, one artist out-deified even the ‘Like a Virgin’ star. Just as Madonna was dominating the cultural conversation by the late 1980s, Michael Jackson was practically worshipped like a god during the Bad era, garnering an almost musical cult of personality among his feverishly devoted fanbase. Such iconic stature hadn’t been seen since Elvis Presley, dwelling in a lofty pop pedestal few could understand, except Madonna, who struck up a unique friendship with the late pop star after inviting him as her date to the 1991 Academy Awards.
“I could certainly relate to him on many levels, but he was also a very shy person,” Madonna shared on Howard Stern‘s SiriusXM radio show in 2015. “He was famous since he was a child and didn’t really have a childhood. He was painfully shy.”
Mutually caught up in the whirlwind of their respective fame, parallel to each other, there was plenty of common ground between the two. “We didn’t really have a relationship about me revealing myself to him, but making fun of the crazy world we were living and working in,” Madonna reflected. “We didn’t talk about our childhoods… I think he felt eternally tortured. It was hard for him to look into people’s eyes.”
There lay the difference. Madonna was able to live a former life as a nobody, know the feelings of dreams and aspirations, melt into the social scene as a young adult, and enjoy all the adolescent milestones before fame came calling. Jackson’s penchant for lapsing into escapist fantasy due to his malformed early years would plague his creative output across the 1990s, unleashing a string of artistically bankrupt records and videos while Madonna was still dictating trends.
Jackson’s force of nature singing and dancing prowess was cruelly exploited by his father and manager, Joe Jackson, the bright Motown pop of the Jackson 5 shrouded by dark allegations of physical and emotional abuse by their supposedly bullying house tyrant. The Jackson story would end on a grim note, as serious cases of child sexual abuse would sour his pop legacy irrevocably.
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