Kenny Rogers Took The First Photos Of Michael Jackson Wearing His Signature Fedora: “Beautiful Pictures… Some No One’s Ever Seen Before”
Kenny Rogers was a major part of pop culture history… in a way you’d probably never expect. The late, great Kenny was good friends with both Lionel Richie and Michael Jackson back in the day, so he was a natural choice to represent country music when it came to the recording of the 1985 hit, “We Are The World.” Of course, the song features vocals from over 45 of music’s biggest names, including the aforementioned writers Lionel and Michael Jackson, as […] The post Kenny Rogers Took The First Photos Of Michael Jackson Wearing His Signature Fedora: “Beautiful Pictures… Some No One’s Ever Seen Before” first appeared on Whiskey Riff.


Kenny Rogers was a major part of pop culture history… in a way you’d probably never expect.
The late, great Kenny was good friends with both Lionel Richie and Michael Jackson back in the day, so he was a natural choice to represent country music when it came to the recording of the 1985 hit, “We Are The World.” Of course, the song features vocals from over 45 of music’s biggest names, including the aforementioned writers Lionel and Michael Jackson, as well as Cyndi Lauper, Bob Dylan, Smokey Robinson, Bruce Springsteen Diana Ross and Dionne Warwick, just to name a few.
It also includes country music’s own Willie Nelson, Waylon Jennings (who didn’t make it until the end of the recording) and Rogers, who said it was “very humbling very quickly” to walk into that studio and see so many legendary musicians in one room.
But aside from being an incredible musical artist, Rogers had a passion for photography, and he released several books with original photos in the 80’s, including one called Your Friends and Mine: A Collection of 80 Photographs, which Michael Jackson was featured in.
And it was around that time that Rogers took the first-ever photos of Jackson in his signature fedora. He wore it as a child and teenager when he was in the Jackson 5, and here and there during other performances, but he notably wore it in “Billie Jean” music video in 1983, and it became iconic when he debuted the moonwalk during a performance of the song at the Motown 25th anniversary special.
Of course, Jackson’s skin and face changed a lot following this performance, and he had multiple facial surgeries that change his look drastically, and so the fedora became a signature part of his look not only for it to be an accessory onstage, but to cover up some things he didn’t want everyone to see all the time.
Rogers recalled being the first one to shoot photos of Michael with the hat on when it became standard wear for him, because Jackson wanted to see if the shadows would completely cover his face and how it would look on film. In an interview with Dan Rather many years ago, Rogers also remembered his special time with Michael when he came to have his photograph taken with his chimpanzee, Bubbles, and he stayed much longer than 15 minutes at Rogers’ studio:
“You know, I did a photography book called ‘Your Friends And Mine.’ And I had a building in LA, and a studio in it. Once I got Elizabeth Taylor and Michael Jackson, people were calling me to be in it. And the reason I think I got so many people like George Burns, and Lucille Ball, and Gregory Beckett and all of these guys is that I promised everybody they’d be in and out in 15 minutes.
Because I was shooting in 8 x 10 format, so you have to have a separate piece of film for every shot. I said, ‘I’ll shoot two colors and two black and whites, and if you don’t like what I get, we just won’t put it in the book.’ Well Michael… I said, ‘You’ll be in and out in 15 minutes.’ He stayed eight hours. He came over and he brought Bubbles, his chimpanzee with him, and we sat and talked.
And I think when you get, it’s like Elvis, when you get to that status, you don’t have a lot of people you can just talk to. He couldn’t go anywhere. He couldn’t be a person. And we talked about… I shot the first pictures of him with the hat. Because I think he was gonna have some surgery done, and he wanted to see if the shadows would cover it. And they’re beautiful pictures, some no one’s ever seen before.”
What a story… to have been a fly on the wall during that eight hour conversation, too. It’s incredible to just imagine what they would’ve talked about, and I love that they were such good friends and had such a strong connection.
Plus, for Rogers to have been entrusted with taking the first fedora photos is just so cool… Michael didn’t need some fancy professional photographer, he trusted Kenny, and the rest, as they say, is pop culture history. I mean, Michael Jackson and his fedora, which he wore often while doing his iconic moonwalk, is one of the most recognizable and famous images of all-time, and it’s so interesting to know what kind of a role Kenny Rogers played in bringing that all together.
Legendary, to say the very least… what I would give to see the unpublished photographs that helped shape the imagine of Jackson as a global solo artist and the all-time great in pop music.
You can watch the full interview here:
The post Kenny Rogers Took The First Photos Of Michael Jackson Wearing His Signature Fedora: “Beautiful Pictures… Some No One’s Ever Seen Before” first appeared on Whiskey Riff.