In 1977, a Minneapolis teenager needed his photo taken. He was vying for a major record label's attention, but he didn't have professional headshots. After hearing the 19-year-old's demo, photographer Robert Whitman had no reservations—he was starting his career, needed fresh material, and agreed to take portraits of the unknown teen. That's how he met Prince Rogers Nelson. The photos helped Prince score a deal with Warner Bro. Records and launch his career. We all know Prince's story. This one is Robert Whitman's, who was our first-ever Life House guest in Little Havana.

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The Setting: First trip you ever took?

I took a trip around the world by myself when I was 18. It got me thinking about traveling and living on the road. At that point, I wasn't a photographer, so all I have are my memories. In particular, one place that stands out is India, where I lived on a tea estate for two weeks.

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The Plot: How did you get your first big break as a photographer?

I worked with Men's Health in New York, where I learned of a big ad campaign for Dewar's. They asked for my portfolio and hired me to shoot a handful of ads, which led to 20 ads. It was one of the biggest campaigns of the 1990s—it started the lifestyle movement in advertising and photography. It won award after award and changed my whole life.

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The Characters: Who have you most enjoyed photographing?

I'm very fortunate that my claim to fame is shooting with Prince before he was famous. I was a young photographer in Minneapolis, and he was an amazingly talented musician—we were just two guys creating images. We did three sessions, and they're some of the most real, authentic photos of him because there was no publicist, no manager, no one controlling the shoot. 

I photographed the singer Aaliyah in Jamaica and Los Angeles for a magazine called YM. And I shot Johnny Depp for the 1985 film Private Resort before he was well known.

Wherever I go, I like to shoot artists. The ballet dancer Mikhail Baryshnikov is one of them. We didn't do the typical dancer shots. Instead, he jumped in the pool and swam around in a tuxedo.

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The Conflict: What's your biggest challenge as a photographer?

Keeping up with new technology is a challenge. I'm old school. I like shooting on film, and I love having my camera on automatic. I shoot digital, and I try to post on Instagram, but I'm not into Photoshop and over-edited photos. I'm a free spirit, and I like my work to reflect that.

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The Theme: What unifies your work?

I seek out real, authentic people to shoot. And I think this is why I love Cuba so much, because it’s so real. In the late 1990s, I took thousands of photos, which eventually became a part of my Cuba Raw series. At this hotel in the suburbs of Havana, the hotel had this amazing swimming pool. An ocean pool. One time I went and there were these bodybuilders who were laying in the sun with their boots. Then there was this beautiful young girl dressed all in white standing by the edge of the pool smoking a cigarette. Wherever I go, I like shooting the people. And I love trying to get into their lives.

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Point of View: A favorite story about staying in a hotel?‍

I love hotels. If I could live in a hotel, I would. Back in the day, I was good friends with Tony Goldman, the owner of Park Central Hotel on South Beach. I used to live at the hotel in the winter, and we did shoots there all the time. I fell in love a few times at that hotel and even had my heart broken once when a girl I was in love with left me for Mickey Rourke. I had so many crazy times in hotels.