Michael Jackson, the undisputed King of Pop, was not only known for his groundbreaking music and unforgettable performances but also for his lavish lifestyle, which extended into the world of fine art. Among the most fascinating aspects of Jackson’s private world was his extraordinary personal art collection—an imaginative and deeply personal archive filled with opulent, mythological, and self-reflective portraits.

Throughout his life, Jackson spent millions commissioning artwork that reimagined him as everything from a modern-day monarch to mythical figures. Many of these pieces were created by some of the most talented portrait artists in the world. These paintings served a dual purpose: to project an idealized version of himself to his fans and to reshape the image he saw in the mirror—one he struggled with since childhood.

According to those closest to him, Jackson had an intense relationship with his own image. He would often avoid mirrors, battling a long-standing inferiority complex. His brother Jermaine Jackson once stated that the more Michael looked at himself, the unhappier he became. Portrait artist Nate Giorgio explained that Jackson’s self-commissioned portraits were an attempt to portray the version of himself he wished to be.

The portraits often depicted Jackson in regal costumes set against extravagant backdrops reminiscent of French royal courts. In many, he wore royal robes or armor, standing alongside symbolic figures such as angels, children, or even his pet chimpanzee, Bubbles. One artist, Ralph Wolfe Cowan, painted Jackson multiple times. One of Cowan’s best-known works showed Jackson in full armor with a sword and parrot, though Jackson famously requested the removal of German Shepherds from the painting, stating simply: “I don’t like dogs. I like monkeys.”

Cowan was paid $30,000 for that particular eight-foot-tall portrait, which was later seen in the background of Jackson’s iconic 1993 interview with Oprah Winfrey. Yet, like many of Jackson’s collaborations, their working relationship ended abruptly. Cowan likened it to working for a king—if Jackson no longer wanted you, he simply stopped calling.

One of the most prolific and enduring artist relationships Jackson had was with David Nordahl. Their partnership began with a late-night phone call in 1988, which Nordahl first assumed was a prank. The pop star had seen Nordahl’s work in Steven Spielberg’s office and was captivated by it. Their initial conversations led to art lessons, and eventually, Nordahl became Jackson’s full-time portraitist for the next 17 years.

During that time, Nordahl produced thousands of sketches and around a dozen major oil paintings for Jackson. These paintings were rich in symbolism, grandeur, and fantasy. One such work, Field of Dreams, was a massive piece that depicted Jackson leading a group of children—among them real-life figures like AIDS activist Ryan White and actor Macaulay Culkin—through a sun-dappled path, symbolizing innocence and unity. Jackson wrote heartfelt notes to Nordahl to ensure the artwork reflected genuine human emotion and the “wonders of childhood.”

Another significant project was a series of paintings featuring Jackson being knighted and crowned—an image he wanted immortalized with poetic grandeur. For the first time, Jackson imposed a deadline on the artist, indicating the personal importance of the series.

Jackson also drew inspiration from classical works and artists such as Michelangelo. One Nordahl painting was based on The Return of Spring and included cherubic figures Jackson lovingly referred to as his “little angels.” In another, Nordahl used Michelangelo’s David statue as a reference for Jackson’s posture.

His artwork wasn’t limited to self-portraits. In 1995, Jackson commissioned a painting of himself and then-wife Lisa Marie Presley. The romantic piece, titled Camelot, was postponed due to other projects, and by the time it was completed, the couple had parted ways.

Nordahl often spoke of Jackson’s insecurities about his appearance. “He always considered himself to be extremely ugly,” Nordahl recalled. But despite Jackson’s struggles, the artist remembered how kind, humble, and deeply thoughtful Jackson was in private. “I would look into his eyes and I could see for a thousand miles,” he said. “Those eyes were unbelievable.”

Ultimately, Jackson’s art collection offers more than just a glimpse into his luxurious lifestyle—it reveals the dreams, fears, and imagination of one of the most enigmatic figures in modern history. Through these paintings, Michael Jackson crafted a parallel universe where he was forever young, powerful, and beautiful—a world of fantasy that shielded him from the often cruel reality outside.