A digitally altered photo of Sam Jennings, found on his Facebook page. From 1998 to 2007, the Proviso East graduate ran Prince's fan website and designed many of his albums and much of his merchandise, among other duties.

Just months before his untimely death on Thursday at the age of 57, pop icon Prince announced that he’d signed an exclusive deal with Jay-Z’s independent streaming music service Tidal. Today, utilizing the internet, social media and other digital innovations to connect directly to fans, and to maintain financial and creative independence, is all the rage among artists.

But Prince was talking about that stuff 20 years ago, said Sam Jennings. Jennings should know. The Proviso East graduate (Class of 1989) was present at the creation. For nearly 10 years, Jennings literally worked side-by-side with the legendary artist as his in-house graphic and web designer.

“When we were first coming up with ideas, we spent a lot of time thinking about how we can utilize this tool [the internet] to connect to fans directly,” Jennings recalled during a recent phone interview.

“There really wasn’t anybody doing this back then. I think that’s why we had those discussions about what we were going to do. There was no social media, none of what’s out there now. It was really just about connecting with fans.”

Jennings landed his job with Prince in 1998 after he’d connected with the artist through an online fan community.

“When the internet first became a thing, I started web designing,” Jennings recalled. “I was a really big Prince fan and so I got connected with his online community. One year, he started hitting up the fans to see if any of us had certain skills he wanted.”

That Prince would seek to hire his own web and graphic design team was a rarity, Jennings said.

“Most artists rely heavily on their record label or managers to handle all that stuff,” he said. “Most musicians don’t want to deal with the details or don’t invest that heavily in web projects. Prince was doing this at a time when there weren’t a lot of companies doing these things.”

Initially, Jennings’s work was project-based, but after Prince discovered the Proviso East graduate’s talent, he hired him full-time to do everything from merchandise design to website management.

Eventually, Jennings would run the NPG Music Club, an official Prince website, which included a radio show, original skits and commentary. At its peak, the site boasted “hundreds of thousands of members,” as Jennings once told the New York Times.

Jennings would work remotely from Chicago most of the time, commuting to Paisley Park Studios about once a month to catch up with the artist.

“I actually had office space in there,” Jennings said. “Paisley started out as a commercial studio, which Prince would rent out to other artists and film crews. Eventually, in the mid-1990s, he took it over for himself.”

The space’s transformation is one of the few predictable aspects of the notoriously mysterious musician.

“There were clouds painted on the walls, murals, live doves,” Jennings said.

Real doves?

“Yep, there were real doves. I could hear them all day making noises in those cages.”

Another predictable aspect of Paisley was the music, Jennings said. The whole space centered on its three music studios, which Prince practically lived in. The music was also the way Jennings and the pop superstar bonded. It was a relationship Jennings described as rooted in respect and courtesy.

“He liked some artists that a lot of people wouldn’t expect him to like,” Jennings recalled. “He liked Kate Bush and Tori Amos. He really liked her. Of course, there was also the music that you would expect, like Stevie Wonder.”

Jennings said his own somewhat eclectic musical preferences were shaped by his upbringing in nearby Maywood.

“Growing up in Maywood, I was around a lot of diversity,” Jennings said. “I’m a white person, obviously, so I was a minority exposed to all kinds of music. Where I lived, there was a really big Mexican population, as well as many African-Americans. So, I probably became a Prince fan early on because of that exposure. I was a huge fan of ‘Purple Rain’ and ‘1999.’”

That exposure was important to developing the kind of cultural sensitivity that one might expect of a person who Prince let design at least three of his album covers and CD packages — “Musicology,” “3121,” and “Planet Earth.”

In 2007, Jennings left the Purple One for a job working with the rock band Pearl Jam in Seattle, where he currently works as a prototype designer with Microsoft.

That’s where he was headed on Thursday morning.

“I’m walking into the building and all of a sudden my phone starts going crazy,” Jennings recalled. “People were texting me, ‘Have you heard?’ ‘Is it true?’ A huge part of my identity is tied up with having worked for Prince. People started calling me the Prince guy.”

Jennings said his mother called him and gave him the news. For a while, he said, he sat at his desk and searched online before leaving work early.

“I just went home and spent the next 12 hours plugged into Facebook to see if this was really happening, if it was really real,” he said, apparently choking up. “I’m still in shock. I don’t believe it. Part of me feels like he’s going to pop up and have a press conference.”

Jennings said, after he left his job with Prince, the two got in touch a few times, but it was hard sustaining a connection. Most of his co-workers at Paisley Park had moved on as well.

“Prince is very forward-facing, he doesn’t tend to look back and reminisce,” Jennings said. “But I always felt like I would bump into him again. I always felt like I’d see him again. To be around him, you feel like he’s one of those guys who is going to live forever. He had such a spark and such energy. It doesn’t make sense that he’s not here anymore.”

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