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The Untold Story Behind Prince’s Iconic ‘Sign O’ the Times’ Album Cover

Images of Prince by photographer Jeff Katz reveal the artist’s enduring impact.

Vogue

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'Sing o' the Times' album cover

Photo: Jeff Katz Photography

There is only one Prince. The music legend may have left us in 2016, but his legacy lives through countless songs, videos, and visuals. There is always something original to discover within his prolific catalog. The launch of an extended version of 1987’s Sign O’ the Times on September 25 treats fans to new music and a host of previously unseen treasures. At present, the 24-hour news cycle and infinite content scroll rarely offer time to gain perspective on albums or experience yearning for the performers who create them. Yet back in 1987, Prince was the master of leaving his audience wanting more. The critically acclaimed album gave the world hits like “U Got the Look” and “If I Was Your Girlfriend.” However, several LPs worth of music was left on the cutting room floor. This year’s massive reissue comes complete with 45 unreleased studio recordings straight from his vault. 

For those who witnessed the process firsthand, the album still brings up fond memories. For Jeff Katz, who served as the artist’s photographer during the mid-’80s, Sign O’ the Times remains one of the most resonant releases of all time. A record that touches on poverty, drug abuse, gang violence, and the AIDS crisis, it went far beyond the dance-pop that dominated radio during the era. “It’s such an incredibly poignant and political album,” shared Katz on the phone from Los Angeles. “The music completely holds up; the lyrics are poignant and as meaningful, given our current situation in the world right now.” Katz’s connection to the record runs deep. He shot its now iconic cover, and the rerelease came with a portfolio of images of Prince from the photo sessions and beyond.

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Photo: Jeff Katz Photography

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Photo: Jeff Katz Photography

At the start of his photography career, Katz was shooting imagery for Warner Bros. Records, working his way up the ladder in Los Angeles. A few years after graduating from Ithaca College in upstate New York, Katz was presented with the opportunity of a lifetime: working with Prince behind the scenes. At the height of his ’80s pop-culture domination, Prince had been shot by many of photography’s luminaries, but he wanted to collaborate with someone who could bring his vision to life. “At that time he had the Paisley Park label, his band called The Family, and he’d already won an Academy Award for Purple Rain. He’s one of the most famous people on the planet,” explains Katz. “He needed someone he could work with and share ideas, not someone who already came with a specific style.” 

Katz’s relative newness worked in his favor. Open to experimenting and going the extra mile to execute a concept, he made an impression during their first meeting, shooting the cover of 1985’s The Family album. “I walked up to him, shook his hand, and said, ‘I’m here to do whatever you want to do,’” says Katz. “We spent the entire day collaborating on shoots and setups. After an hour, he just had me shoot the whole thing, and I realized that we got along well.” Working together meant translating the famously terse musician’s desires into visuals. “I was given the framework, esoteric concepts—I almost had to be a mind reader early on,” says Katz. “He didn’t overexplain; he trusted me to understand. [Over time] he learned more about photography, but he trusted me to bring his vision to the pictures.”

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Photo: Jeff Katz Photography

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Photo: Jeff Katz Photography

The successful shoot quickly led to other opportunities, namely a gig shooting behind the scenes of Prince’s directorial debut, Under the Cherry Moon, the album cover for his 1986 release, Parade, and a spot as his official tour photographer. Though Katz was present for many Prince milestones, the Sign O’ the Times session stands out as a highlight. At the beginning of their working relationship, Katz was contacted for assignments via management, but after months of being on the road together and building a rapport, the artist reached out personally. “He just calls and goes ‘Would you take my picture?’” says Katz. “I would never ask why. I just said, ‘Sure,’ and had all my gear ready.”

A warehouse in Eden Prairie, Minnesota, close to the future location of Paisley Park, served as the shoot’s set. “I walk in, and it is empty, except for a drum kit sitting on top of the riser,” says Katz. “That was it.” These days nearly every shoot involves weeks of planning and teams of people, but when Prince and Katz worked together, the process was stripped down and organic. Case in point: That striking yellow look on the album’s cover was achieved without a stylist’s input. “I’ve worked with many pop stars, rock stars, rappers, bands—you name it, but the thing that set Prince apart from everyone else was that for each album, each theme, and type of music, he embraced it fully,” says Katz. “Those are his ideas, clothes; the style and accessories came from his artistic vision for the project and himself. He had a whole wardrobe department at Paisley Park that worked round the clock on his entire look, and it’s not like he wore stage clothes then throws on a T-shirt and jeans. That was his look 24/7.” 

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Katz behind the scenes with Prince Photo: Jeff Katz Photography

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Photo: Jeff Katz Photography

The digital retouching and editing now routine on photo shoots from magazines to Instagram was also nonexistent. Katz worked entirely on film, designing the lighting himself. “There is no photo manipulation, no composites. It was all done old school,” he says. “Every image you see exists on a piece of film; the colors are exactly how they appeared in life.” At first glance, the cover photo’s multilayered look might seem like a collage, but it was created using a variety of props and backdrops in the studio. “The props had been taken from his apartment,” says Katz, who recalls the artist’s attention to detail. “He always wanted to see the film afterward; he would just hold it up to the light and see it.” Even the slightly out-of-focus blur that features in the final photo was a result of Prince’s willingness to think outside the box. “The shoot was pretty much over, and I had an apple box sitting in front of the camera, he just walked up to me with a smirk,” says Katz. “He sat on it, put his face right up to my lens, and so I shot it. Without even seeing it, he laughed and said, ‘That’s the cover.’”

Those kinds of organic interactions between subject and photographer are increasingly rare. The “fix it in post” mentality and speed of digital creation can become a hindrance, but back in the ’80s, that wasn’t an issue. “It was just him and me at work,” says Katz. “When you’re creating without being self-conscious, you’re letting yourself go, and that’s why when the pictures are shot on film, you can see more of the person in there. If you shoot thousands of digital images, you are basically using a video camera, and you can miss those jewel moments. That’s what I try to tell people, especially younger photographers. Slow down, shoot less, think more, and compose your shots.” 

The intimacy that approach creates is evident in Katz’s photographs of Prince. The two would go on to travel the world together on tour and create classic images for several more albums, memories that have stuck with Katz three decades on. “He taught me so much about how to think on my feet and create at a moment’s notice, how to make things happen organically,” says Katz. “I’ve carried those lessons to each photo shoot that I’ve done since. It was a baptism by fire; people always ask if I was nervous [working with him], but you didn’t have time to be nervous. We fully embraced it and just dove right in. I remember every shoot we did and place we traveled like it was yesterday.”

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Photo: Jeff Katz Photography

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This post originally appeared on Vogue and was published September 10, 2020. This article is republished here with permission.

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