In the rarefied air of pop royalty, Michael Jackson stands alone, an artist whose shadow looms over the entirety of modern music. His albums were not mere releases; they were global events. His music videos were not promotional clips; they were cinematic short films that redefined a medium. But for an artist who defined collaboration with “We Are the World,” Jackson’s solo career is equally defined by the ghosts of partnerships that never were.

The history of music is littered with “what ifs,” but the list of artists who almost, almost worked with Michael Jackson is a veritable Hall of Fame. These weren’t just missed connections; they were seismic shifts in music history that failed to happen, often for reasons so shocking, so personal, or so utterly bizarre, they sound like industry folklore. Yet, they are true. We are pulling back the curtain on the alliances that crumbled, the feuds that ignited, and the egos that clashed, revealing the complex, perfectionist, and fiercely protective man behind the King of Pop.

The Clash of the Titans: When Pop Ate Itself

Some egos are simply too large to share a studio. Such was the case with the two defining male artists of the 1980s: Michael Jackson and Prince.

The year was 1986, and Jackson was recording his follow-up to Thriller. The album, Bad, was conceived with a secret weapon: its title track was written specifically as a duet with his one true rival, Prince. Producer Quincy Jones, a genius in his own right, orchestrated a secret meeting at Michael’s home, hoping to unite the two superstars. The plan was pure marketing gold: Michael and Prince would pretend to feud in the press, only to shock the world with their joint masterpiece.

It imploded on the launchpad. Prince listened to the demo, his focus narrowing in on the song’s very first line: “Your butt is mine”. As he later told Chris Rock, the ambiguity was a deal-breaker. “Now I’m saying, ‘Who’s going to sing that to whom?’ Because you sure ain’t singing it to me, and I sure ain’t singing it to you”. The meeting was tense. Prince reportedly questioned the entire song, and the greatest pop rivalry collaboration of all time died before a single note was recorded.

If the “Bad” duet was a battle of male egos, the intended collaboration for “In the Closet” was a clash of artistic philosophies. Before Princess Stephanie of Monaco laid down the breathy, mysterious vocals, the part was offered to Madonna. Fresh off her “Justify My Love” controversy, the Queen of Pop was on a mission to push every boundary. Her concept for the video was pure provocation: Madonna would dress as a man, and Michael would dress as a woman.

Michael, however, was in a different place. Increasingly besieged by speculation about his personal life, he recoiled from the idea. He wanted art; she wanted a statement. “I said, ‘Well, why come to me?’” Madonna later lamented. “It’s like asking Quentin Tarantino not to put any violence in his films”. She found Michael “too shy” and walked away, leaving another dream duet to dissolve.

The Llama, the Chimp, and the Unbelievable

While ego and creative differences are common in the industry, some of Jackson’s failed partnerships defy all logic. The most legendary involves the golden-voiced frontman of Queen, Freddie Mercury. In 1983, Mercury and Jackson were actively working in Michael’s home studio, laying down tracks for “State of Shock” and “There Must Be More to Life than This”. The fusion of two of the greatest vocalists in history was underway.

Then came Louie. Michael, famously eccentric, brought his pet llama into the control room. For Freddie, a man known for his own wild eccentricities, this was a step too far. Queen’s manager, Jim Beach, received a frantic call from the singer: “You have to get me out of the studio. I’m recording with a llama”. The sessions collapsed. While some sources point to Mercury’s rumored drug use in Michael’s drug-free home as a point of friction, the llama remains the incident’s furry, inexplicable mascot.

In an equally bizarre, though likely apocryphal, tale, a collaboration with hip-hop pioneers Run DMC was also allegedly derailed by an animal. A track titled “Crack Kills” was reportedly in the works during the Bad sessions. The urban legend claims the partnership ended when Michael’s pet chimpanzee, Bubbles, bit Jam Master Jay. The more plausible explanation? Creative differences. Run DMC’s raw, stripped-down sound was the antithesis of Michael’s polished pop, and the two worlds simply couldn’t merge.

Perfectionism, Protectionism, and the Rap Game

As Michael’s career progressed, his perfectionism became a fortress. He was an artist who would rather release nothing at all than release something that was merely “good.” Hip-hop legend LL Cool J learned this firsthand. The two recorded multiple tracks together in the early ’90s, including “Serious Effect,” intended for the Dangerous album. Insiders called it an innovative fusion, but Michael ultimately shelved it. “They weren’t good enough,” LL Cool J admitted decades later, not with bitterness, but with respect for Michael’s impossible standards.

This protectionism extended beyond his music to his personal loyalties. When producer QD3, son of Quincy Jones, approached Michael to feature on Tupac’s “Thug Nature,” it seemed like a perfect fit. The track cleverly sampled “Human Nature”. But this was the height of the East Coast vs. West Coast feud. Michael had already worked with Tupac’s sworn enemy, The Notorious B.I.G., on the song “This Time Around”. Michael’s reply was simple and final: “He liked Biggie”. Loyalty, it turned out, trumped a collaboration, and Michael refused to be drawn into the war.

Even Pharrell Williams, the Midas of 2000s production, couldn’t crack the code. He produced eight tracks specifically for Michael, none of which were used. Some eventually found a home with Justin Timberlake. Pharrell later said that Michael admitted he regretted passing on them.

The Lines That Can’t Be Crossed

For all his eccentricities, Michael Jackson was a deeply sensitive man, and disrespect was a non-negotiable offense. Two of music’s biggest white rappers learned this the hard way.

Dr. Dre, the architect of West Coast hip-hop, was rumored to have disrespected Michael in a song. Whether it was a joke about his appearance or personal life, it was enough. Despite their similar circles and Michael’s interest in contemporary sounds, the King of Pop allegedly refused any and all opportunities to work with him.

But no feud was more public, or more painful, than the one with Eminem. In 2004, Eminem released the music video for “Just Lose It,” which featured a grotesque and brutal mockery of Jackson. The video parodied Michael’s plastic surgery, the child abuse allegations, and his changing skin color. For Michael, who was in one of the darkest periods of his life, this was not satire; it was a cruel and devastating blow.

He was crushed, but he was also a businessman. Michael’s response was not a diss track; it was a checkmate. He instructed his team to purchase the rights to Eminem’s entire publishing catalog. In one move, Michael Jackson became the owner of his tormentor’s work, earning money from every song Eminem sold. He then made it clear to his management: he would never work with Eminem, under any circumstances.

The Duets That Business Broke

Sometimes, the reasons were heartbreakingly simple and had nothing to do with Michael at all. For his soaring Bad ballad, “I Just Can’t Stop Loving You,” his first choice was not Ceda Garrett. It was Barbra Streisand. But Streisand, 16 years his senior, declined. She felt the romantic lyrics would be “unbelievable” and inappropriate coming from them, a quaint notion by today’s standards.

Even more tragic was the lost duet with Whitney Houston. At the peak of her powers in 1987, she was Michael’s choice for the same song. The combination of their voices would have been revolutionary. But Houston’s label, Arista Records, blocked it. They feared the collaboration would overexpose their star and interfere with the promotion of her upcoming second album. Business, in its infinite short-sightedness, chose album sales over one of the greatest duets in history.

In the end, the artist who respected Michael’s legacy the most was will.i.am. The two worked closely in Michael’s final years. After his death in 2009, the industry was rabid for unreleased material. will.i.am had tapes worth millions. He refused to release a single one. “He was a perfectionist,” will.i.am explained, “he wouldn’t want unfinished songs out there”. It was the ultimate act of respect, a quiet testament to the perfectionism that defined, and sometimes limited, the most singular artist the world has ever known.