Michael Jackson’s appearance has always been a subject of fascination and speculation. While much of the conversation around his evolving looks has focused on his well-documented plastic surgeries, many overlook the crucial role makeup played in shaping his iconic image. Jackson’s commitment to his appearance was more than just cosmetic surgery—he worked tirelessly with makeup to perfect his look and transform his face, not just for his music videos but also as part of his everyday routine.

Throughout his career, Jackson was incredibly dedicated to his image, often making requests to his personal makeup artist, Karen Faye, like “hurt me, hurt me,” meaning that he wanted his appearance to be so flawless it almost seemed painful. This phrase symbolized his desire to achieve perfection and impress his fans. It wasn’t just about looking good—it was about creating a look that could take people’s breath away.

Jackson’s focus on his looks began early. As a child star with the Jackson Five, his image as a cute, charismatic performer was one of the group’s major selling points. However, as he entered his teenage years, he battled with acne, a condition that many young teens find hard to cope with. This struggle was magnified due to his immense fame, and Jackson often turned to makeup to cover his imperfections during performances or photo shoots.

As Michael Jackson’s solo career took off, he became increasingly meticulous about his appearance. He often said that one should always aim to look better and perfect one’s image, something he applied not just to his stage persona but to his day-to-day life. Makeup was an essential part of this. Jackson loved not only the transformative nature of makeup to enhance his beauty but also to create characters, such as his portrayal of the Scarecrow in The Wiz and later the werecat in Thriller.

The Thriller music video was a landmark moment in Jackson’s career, where makeup became a powerful tool for transformation. Jackson worked with Rick Baker, a prosthetics artist who had previously worked on An American Werewolf in London, to create his werecat look. The transformation involved intricate prosthetics and silicone molds, as well as every imaginable shade of stage makeup, showcasing Jackson’s desire to push boundaries and experiment with his image.

During the Victory tour in 1984, Michael Jackson’s commitment to his image was evident. A photo taken backstage shows him applying his own makeup before a show. His makeup routine was a symbol of his growing interest in androgyny and gender fluidity. Rather than adhering strictly to femininity, he blurred the lines of gender expression, something that would continue throughout his career.

As Jackson’s fame grew, so did his dedication to his looks. The success of Thriller in particular pushed him to achieve a higher standard of physical perfection. He slimmed down significantly, wore heavier makeup, and employed new techniques such as contouring to accentuate his facial features. This shift became evident in his stage appearances, where theatrical makeup like base, concealer, eyeliner, and eyeshadow helped him look flawless under harsh stage lights. His favorite makeup brand during this period was Rachel Perry Inc., known for its holistic skincare and natural products.

The change in Jackson’s appearance became more noticeable with the release of Bad in 1987. Speculation surrounding his lighter complexion ignited media debates, with many wondering whether his skin lightening was due to makeup, skin treatments, or surgery. It’s likely that the lighter appearance was a combination of both makeup and the effects of his skin condition, vitiligo, which causes patches of lighter skin. Makeup, such as Lancome dual finish powder, became essential in giving him a smooth, even tone, which was necessary for both his on-stage performances and public appearances.

As Jackson’s skin condition developed, makeup was used increasingly to cover up patches of vitiligo. Dermablend, a heavy-duty foundation designed to cover severe skin imperfections, became a key product in Jackson’s routine. His makeup was so intricate during his Dangerous era that it resembled a mask, a way to shield himself from public scrutiny and protect his privacy from the harsh tabloid press. His makeup routines became more exaggerated, with darker eyeliner and dramatic contouring to hide his condition and maintain a smooth, flawless appearance.

In the early 1990s, after enduring public criticism and harsh media attacks, Jackson’s makeup style became even more intense. He started experimenting with more dramatic looks, including the application of lipstick and eyelash extensions. The long-term effects of his lupus condition, which caused hair loss, likely led to these experiments. Eyebrow tattoos and permanent makeup became necessary for Jackson as he continued to fight the challenges of his changing appearance.

By the late 1990s, Jackson’s look softened somewhat, although makeup remained an essential part of his public image. Despite the physical toll of years of cosmetic surgeries and medical conditions, Jackson’s dedication to his beauty routine never wavered. His makeup became a way to not only cover imperfections but also express his identity as an artist, constantly experimenting with his look in ways that mirrored his constant reinvention on stage.

Michael Jackson’s makeup journey was about more than just covering imperfections—it was about crafting a persona, experimenting with new identities, and shaping how he was seen by the world. His evolving beauty routine was a testament to his relentless pursuit of perfection, both on and off the stage.