Nearly twenty years ago, I walked into Philadelphia Java Company and I met James Dean.

There was an undeniable coolness about him: the cigarette with the mile long ash hanging from the corner of his lip and a swagger to his walk as he sauntered up to get a cup of black coffee. He had a penetrating gaze— well, at least that’s how my mind’s eye remembers him. With my deep rooted shyness long behind me, I marched right up and asked him his name.

“Dylan,” he said.

Of course your name is Dylan, I thought. It couldn’t have been more fitting.

Dylan played guitar in a Philadelphia rock band called Valsalva and he is the son of the late Jay McConnell, former owner of famed Philly dive bar, Dirty Frank’s. We talked for a bit and I announced that I was a photographer and that I’d love to photograph him. Without hesitation, he agreed.

As a self taught photographer and only three years in at the time, I was eager to shoot “in-studio.” So, I called Milton Perry. Milton was one of my first photographer friends and he had an amazing photography studio in the loft district. Once the studio was secure, I began fixating on how I was going to photograph Dylan. Because he had such a classic and iconic look, I quickly decided on a white seamless backdrop.

There was only one tiny problem: I had NO IDEA how to do it— Again, self taught.

So, I set off for the now defunct Abbey Camera.  John Kreidler, Greg McIlhenny, and Andy Bolton were the absolute best— I peppered them with questions, which they expertly answered and  they helped arm me with the gear I needed to pull off the photo shoot.

August 28, 2000— the day of the shoot. I arrived at the studio early and was fully charged, completely ready for the challenge. My assistant was a guy named Todd, whose last name I can’t remember to save my life! We had a full sweep set up, strobes with soft boxes and umbrellas on stands, and my beloved Hasselblad on the tripod. To say I was happy, well— what an understatement.

Dylan arrived on time and was wearing the most perfect, well-worn white t-shirt. Of course he was. Didn’t I tell you he was James Dean?

Todd and I tweaked the lights and after double checking my exposure and composition, I was good to go.

On set we listened to the Red Hot Chili Peppers record, “Californication” on repeat. (*At the time, my brother, Aaron, and I were obsessed with the song “Scar Tissue.”) “With the birds I share this lonely view…” Anthony Kiedis sang as I snapped photo after photo of Dylan. Only it wasn’t a lonely view for me— I was wide-eyed and my heart was full.

It’s now almost twenty years later, and in my home in Philadelphia— in a very prominent spot— hangs a massive 40×40 print of Dylan from that photo shoot, framed in steel. When people come into our home, they often blurt out: “Wow! That’s ‘Rebel Without a Cause!'”

“Yep,” I say with a smile. “That’s Dylan.”

*Dylan now lives in California and has two daughters. He is a graphic designer specializing in logo and web design, as well as brand identity.

Shot with a Hasselblad 501CM