I first met Gordon Willis ten years ago, when I was stalking him. At the time, I was a recent NYU film-school graduate/loser and I had spent all the money I had in the world traveling through New Zealand, Australia, and Fiji. I was broke and back on Cape Cod—where I grew up—working the overnight shift at the Stop & Shop, trying to save money to move to California. It was while I was stuck in this supermarket that my parents told me that Gordon Willis had moved in across the street.

Gordon Willis is the cinematographer of some of the greatest movies of the 1970s and 1980s—The Godfather I and II, Klute, All the President’s Men, The Paper Chase, Annie Hall, Manhattan, Interiors, Stardust Memories, Zelig. He was born in 1931, in New York City, and received the Governors Award from the Academy of Motion Picture Arts and Sciences—a lifetime-achievement Oscar, to be blunt—for his work as a director of photography. He maintains a lovely garden outside the home he shares with his wife, Helen. Their home has a view of the local cranberry bog, making it the envy of the neighborhood.

That miserable summer, I made it my goal to befriend Gordon, in the hopes that some of his success would rub off on me. I documented this effort in a short story called “Stalking Gordon Willis,” which was run by McSweeney’s Internet Tendency in 2003. A few months later, Gordon appeared in my kitchen and said, “So, Chris, I hear you’re a writer.” I knew then that he had Googled himself and seen my story. He was cool with it.

It is now a decade later, and Gordon and I are friends. We email from time to time. He gave me his personal copy of The Landlord, Hal Ashby’s debut movie and one of my favorite films, for which Gordon was the director of photography. I am now a member of the Writers Guild of America, which means I get movie screeners around the holidays, and at Christmas I make a yearly pilgrimage to his house across the street, knock on his door, and ask him what he thought of the year’s crop of award contenders. He speaks with the snap judgment and inside-baseball perspective of a man who knows his craft cold.

—Chris McCoy

I. YOU COULDN’T GET ME BACK TO THE JUNGLE

BLVR: I wanted to talk about your time with the Air Force Photographic and Charting Service.

GW: When I first went into the Air Force, I did what everybody else...