Visitors to the Simon Gallery in Vineyard Haven often scan the walls covered with famous singers and activists and make some version of the following remark: “Wow, you’ve got all these pictures with all these interesting people in them, you must have amazing stories.”

And photographer Peter Simon does. So he has compiled many of his prized shots and told the stories behind the photos on a pair of discs titled Through the Lens — Celebrating Fifty Years of Personalized Photojournalism.

“It’s really the crowning achievement of my career,” Mr. Simon said recently in an interview in his gallery.

Mr. Simon frequently photographed Bob Marley in concert and at home in Jamaica. — Peter Simon

The DVD set is a nearly four-hour multimedia memoir divided into 12 chapters. Mr. Simon’s journey begins in Riverdale, N.Y., where he grew up, and ends here on Martha’s Vineyard where the 66-year old photojournalist has lived since 1988. Throughout the film, he takes viewers back to the scene when the photographs were taken and recaptures the power of the moment.

“There’s not one thing like it, not one photographer’s life story that’s spelled out in this way,” he said.

Early on, Mr. Simon discovered that his camera lent him a degree of prestige. A victim of bullying in high school, Mr. Simon began to tote around his camera during the school day. When he showed his photographs to his classmates, they were impressed, and he rose in the ranks of popularity.

“If it weren’t for that, I would have withered away,” he said. One early photograph in the DVD shows his schoolmates crowded around a television set, receiving the news of John F. Kennedy’s assassination.

Capturing the Grateful Dead in a light-hearted moment. — Peter Simon

Throughout the years, he has used his camera to get close to the artists and activists he admired. In this way, his DVD serves as a window into an important period of American history. Many of his shots taken in Boston in the late 1960s and early 1970s are iconic, capturing the sex, drugs and rock and roll that marked his generation.

“Anyone that lived that, wants to relive that,” he said.

There is a personalized nature to much of Mr. Simon’s photography. A proud left-winger, he often used his lens to illustrate “us and them” moments during the 1960s and 1970s. His work includes sit-ins, love-ins and the sarcastic peace sign of a disapproving police officer.

“We thought we were all one,” he recalls in the video. “We thought it was a new dawn and a new life where we were all going to be friends.”

Often Mr. Simon found himself in the thick of the struggles against the status quo. At particularly violent protests, the photographer thought: “The rest of my life I am going to be in a wheelchair,” he recounts in the DVD.

Huge rally on the mall in Washington, D.C. — Peter Simon

One particularly striking photo of this period shows a row of seated schoolkids waiting for the bus, blissfully unaware that there is a homeless man sleeping on the roof of the bench above them.

This intimacy with his subject matter continues in the chapter titled Decent Exposures. For a time Mr. Simon lived on a commune called Tree Frog Farm and his pictures capture the nudism that were part of his commune life. There are pictures of his friends cavorting naked in the snow, riding horses bareback, gardening naked and “canuding” along a nearby river. The series continues with photographs taken at a nudist convention in Florida, and of nude bathers at Lucy Vincent Beach in Chilmark.

There is no shortage of famous subjects in this collection. From an early age, Mr. Simon seems to have found himself in the right place at the right time — and always with a camera. He photographed Robert Kennedy, Martin Luther King Jr., Jackie Robinson (a close family friend), Howard Zinn (his professor), Allen Ginsberg, Bob Dylan, Jerry Garcia and the Grateful Dead, to name a small fraction of his subjects. He shot several covers for Rolling Stone magazine and during one memorable moment, Mr. Simon’s lens was clouded by some of Jim Morrison’s vomit.

His career also includes two album covers for his sister Carly. Mr. Simon was the youngest of four siblings — his sisters Lucy, Joanna and Carly were all charismatic performers who attained fame in varying degrees.

Life at the Tree Frog Farm commune keeps on turning. — Peter Simon

“I was intimidated growing up,” he said. “When I first learned my craft, I was very intimidated, socially awkward, with buck teeth.”

Mr. Simon admits to being confronted by the shadow created by his elder sister’s successful musical career, he said, particularly as they both live on the Vineyard. But he has developed his own following through his photography and his annual calendar. Landscape pictures make up most of the shots for both his calendar and the books he published about the Vineyard. Today, many visitors to his gallery are surprised to learn that he led a “wild life” in the 60s and 70s, and documented it through film.

To this day, Mr. Simon is hardly ever without his camera. But even when he does leave his Canon 50D behind, he can snap photos with an iPhone. In 2003, he reluctantly made the shift from 35mm film to digital production. “I went kicking and screaming,” he said. He still has a darkroom in his basement of his Chilmark home, but he rarely uses it.

“In a way, I like it because it puts the camera into the hands of the common man,” he said of the digital age. But it levels the playing field for picture-taking and changes the nature of the profession, he said. “If I were going to make it in today’s world, I would have to think twice about it,” he said.

James Taylor and friend have a reflective pause in Vermont. — Peter Simon

Mr. Simon’s iPhone is a far cry from the magic that originally drew him to the art. Mr. Simon’s father, the late publisher Richard Simon who co-founded Simon and Schuster, was an amateur photographer and was the first to publish a coffee table book that treated photography as art. Richard Simon died when Peter was just 12 and the most intimate moments they spent together took place in the darkroom, where young Peter would watch his father develop prints. His very first photograph was an eerie shot of his father walking alone on a winter day. “There is not much joy in the picture. The sadness is the thing that comes across to me,” he said.

Mr. Simon’s email list includes 6,000 fans, whom he considers the primary audience for the film. A second audience is amateur photographers who will appreciate the DVD’s bonus tracks, which include tips and techniques of the trade. “I am now at the end of my life, and I want to pass on my knowledge to the next generation,” he said.

There were will be a reception for Through the Lens — Celebrating Fifty Years of Personalized Photojournalism from 3 to 6 p.m. on Saturday, Nov. 30, at the Simon Gallery located at 54 Main street in Vineyard Haven. DVDs can be purchased at the gallery or at The last chapter entitled On the Vineyard can be viewed for free via MVTV on demand.