New perspective on looking back

When you’re 62 and still at the height of your productivity, is it too early for a career retrospective? “I’m real flattered, but I’m also quite shy, and the idea of talking about my work on a stage is daunting,” said the photographer and filmmaker Bruce Weber of Montauk.

“It’s different if I’m talking to a writer in a one-on-one setting, that I’ve done. But in front of an audience, this could be a horrifying experience for me.”

But Mr. Weber did say yes to being the subject of “The Artist’s Eye,” a program being presented for the first time as part of the Hamptons International Film Festival. On Saturday at 4:30 p.m. at the East Hampton Cinema, a compilation of his work will be screened, followed by an interview with Mr. Weber conducted by Rajendra Roy, the former artistic director of HIFF who is now the chief curator of film at the Museum of Modern Art.

It had to have been difficult to fit a representative sampling of Mr. Weber’s work into one showing that demonstrates the impact he has had on popular culture. He was born in Greensburg, Pennsylvania, but has spent most of his life in the New York area and traveling to and from photo shoots. He pursued fashion photography, and his cover shots for Andy Warhol’s Interview Magazine and for GQ in the late 1970s earned him a reputation as a pioneer of male fashion and art photography.

The most well-known of his advertising photographs were of scantily-clad, lean and muscular men for Calvin Klein that pushed the envelope of what magazines and billboards were willing to display. Like those, most of his famous photographs have been published in black and white. He has photographed Harry Connick Jr., Jackson Browne, and Chris Isaak for their album covers and worked with the Pet Shop Boys and other performers on music videos.

Mr. Weber has also been involved in documentary filmmaking, most notably “Let’s Get Lost,” a movie on the jazz trumpeter Chet Baker made in 1988, as well as “Chop Suey” in 2001 and “A Letter to True” in 2004, and he has been nominated for an Oscar in the Documentary Short category. He is now at work on a documentary about the iconic actor Robert Mitchum, and of all things, it’s a musical.

“I met Bob on an assignment for Vanity Fair,” Mr. Weber recalled. “We were doing a series of photos on tough guys. He was incredibly generous to me. I didn’t expect that because I had heard so many terrible stories. He was the kind of guy who once you stand up to him, he kind of believes in you. A reason why my movie is a musical is because Mitchum had a fine voice—made two albums during his film career—and I’ve got Elton John and Rickie Lee Jones involved in it.”

He has seen the compilation prepared for Saturday’s event, but that hasn’t meant he has been dwelling on it. “I do like it that the Film Festival is opening up more to shorts and videos, and in my case, even commercials, all kinds of filmmakers,” Mr. Weber said. “But it did make me feel I am too young for this. I’m always beginning projects. There is so much to do. It will be strange to ponder the past.”

A past he doesn’t mind talking about involves the photographers who influenced him, among them Alfred Stieglitz, Paul Strand, and Walker Evans. “It might surprise people that I’m strictly old school,” he said. “I grew up looking at the work of those men. One of my first fashion jobs was for British Vogue, a story on Edward Weston. I photographed Georgia O’Keeffe many years ago, and to talk to her about Stieglitz was a great experience for me. He and Strand and others were heroes to me. I try to teach my assistants about them, I give them books of their photos. It’s more about their courage than to copy what they did.”

Mr. Weber has a genuine passion for making documentary films, a genre of the movie business that few people can sustain financially. “Making a movie is like diving into an empty swimming pool,” he said.

But he continues to do it because ... well, it’s almost like he can’t help it. “I meet a lot of characters in my life,” Mr. Weber explained. “I like that you can go to a bar in Montauk or New York or anywhere and you can bump into a character. I like to be able to say, ‘Let’s make a little film together.’ I like not having a grand plan. You can be making a documentary about somebody and arrive at his or her house and it would be nothing like what I thought.”

Similar to the spontaneity of snapping a shutter? “Yes,” the photographer said, “I like the ‘go for it’ attitude about making movies and taking pictures.”