When you think of Michael Jackson, one of the first images that likely comes to mind is the fedora—tilted forward, casting a mysterious shadow as he slides effortlessly across the stage. That iconic look didn’t happen by accident—and country music legend Kenny Rogers had a surprising role in making it part of pop history.
Kenny, a close friend of both Lionel Richie and Michael, was one of the many artists invited to participate in the legendary 1985 recording of “We Are The World.” While the session itself was packed with over 45 musical legends—from Diana Ross and Bruce Springsteen to Cyndi Lauper and Bob Dylan—Kenny’s connection with Michael extended beyond the music.
A passionate photographer, Kenny released several photo books in the 1980s, one of which was titled Your Friends and Mine: A Collection of 80 Photographs. Among the stars featured? None other than Michael Jackson.
It was during this period that Kenny captured something extraordinary: the first professional photographs of Michael wearing what would become his trademark fedora. While Michael had worn hats in his early Jackson 5 days and sporadically throughout performances, it wasn’t until “Billie Jean”—first in the music video and then during the Motown 25th Anniversary performance—that the fedora became synonymous with his stage persona.
But here’s the fascinating part: Michael wanted to see how the hat would look in shadow, particularly on camera. According to an interview Kenny gave to Dan Rather years later, Michael came to his Los Angeles studio for a scheduled 15-minute session… and ended up staying eight hours. Not only did he bring Bubbles along for the ride, but the session turned into an intimate hangout between two icons.
“I said, ‘You’ll be in and out in 15 minutes.’ He stayed eight hours. He came over and brought Bubbles… and we sat and talked,” Kenny recalled. “He wanted to see if the shadows would cover [his face]… I shot the first pictures of him with the hat.”
At the time, Michael was beginning to make changes to his appearance, and the fedora wasn’t just a stylish accessory—it became a tool, a form of self-expression, and, in some ways, a shield. Kenny’s portraits captured this shift—images that Michael trusted him to take, not for publicity, but to see how he would be seen.
The trust Michael placed in Kenny speaks volumes. He could have chosen any fashion photographer in the world, but he opted for someone he considered a friend. Someone who gave him space not just in front of the lens, but behind the scenes, where he could just be Michael.
Though many of those photos have never been made public, their impact is still felt. The black fedora would go on to be a symbol of Michael’s artistry, elegance, and mystique—woven into performances, short films, and tours for decades to come.
You can watch the full interview here:
Did you know Kenny Rogers played a role in creating one of Michael Jackson’s most iconic looks? Now you do.
