By Amy Conway
Photographs by John Dolan

John Dolan and I both contributed to the first issue of Martha Stewart Weddings magazine, which came out in 1995 and featured a heart-shaped bouquet of velvety roses on the cover. Dolan was a young photographer trying to break into editorial work for magazines. I was a couple of years out of college, an aspiring writer and editor working in a junior role for Martha’s publications. He would go on to become a pioneer in transforming wedding photography into an art form. I would move up the masthead, becoming editorin-chief of Martha Stewart Weddings and other publications. Dolan and his wife would move to Chatham, New York, and raise their family there. I would eventually buy a house in Great Barrington and become editor of The B.

Somehow, despite having started our professional lives in the same place and ending up down the road from each other 30-plus years later, we only met a couple of times in person. I loved his iconic photos, and I knew how much my colleagues respected and enjoyed working with him. So it was a genuine pleasure to catch up with him over grilled cheese at Rubi’s in GB.

“Whenever I lecture, I tell people, there’s no industry without that issue,” he said of that first edition of MSW. “It changed everything.” Bridal magazines had been formulaic, staid, and stiff, as was wedding photography. Martha and team elevated the genre, publishing pictures of real couples, telling visual stories, finally bringing emotion to a topic that is all about emotion. Dolan had more than a dozen wedding photos in that first issue, and his name and phone number were published in the back. He got calls. As more issues came out with more of his work, brides would come to see him with pages ripped from the magazine, saying, “I’ve had this since before I got engaged.”

Dolan and a couple of other trailblazing photographer friends embraced weddings as an important subject, even though “the serious guys we knew, journalists or documentary or fashion people, they just despised it.”

Their work started getting attention from the media and art worlds. So much so that, in 1996, The New York Times published a story about this new school of photographers. It included the following: “John Dolan, a founder of the [I’m Proud to Be a Wedding Photographer] Club who lives in the East Village, said wedding photographers were generally viewed as people who behaved boorishly, blinded the guests with their lights and dressed like Elvis impersonators, among other things.”

“It was a real New York moment,” he says now. “It’s fascinating to be part of a New York moment.”

Rather than an Elvis show, Dolan likens a wedding to a circus. “We come into town, we put up a tent for a onenight show. Monday, it’s gone. There’s a master of ceremonies, there’s a lion tamer. I always see myself as the high wire artist because I have to take risks, but I’m not going to fall. If I don’t take some risks, the pictures will be boring.”

His pictures are never boring.

At a wedding, his thought is “How great can I make this moment? How can I bottle this?” Every wedding has a scent, he says, or pixie dust or a reality that’s otherworldly. Capturing it isn’t easy. “Sometimes I’ll go for a walk in the middle of the reception, then I go back in and think, what is it? Or I listen. I stand at the back. You’ll hear table 13 in hysterics. And then you go over to them.”

And for those who question the excess that comes along with weddings? The pandemic showed how much we need something to celebrate, says Dolan. And every wedding supports small local businesses. “The caterer, the florist. People have been able to have careers and buy a house because of these jobs. The money isn’t going to big pharma or big ag.”

Dolan has traveled the world for weddings and other editorial and commercial photography work. He and his family moved full time to Chatham in 2002; Dolan’s wife, Michele O’Hana, owned the shop Local, in Lenox, and is an artist and interior designer; their three kids, now adults, went to Berkshire Country Day School. (Dolan, O’Hana, and their son Jack, a knife maker, had a show called “HOME” at the Robin Rice Gallery in Hudson this fall.)

During the pandemic, Dolan realized that it was the first time he had spent three weeks in a row with his wife in 30 years because he was on the road so much. They made the most of this found time together at home. “We got sheep and goats and horses and chickens. We fenced half of our property and gave fields to the animals for grazing.” O’Hana knits with wool from the sheep.

“We’re just very rooted here. I look back, this is the longest I’ve lived anywhere in my life. It just happens all of a sudden.”

Dolan now shoots just 10 weddings a year; he also does lectures and workshops. For those 10 weddings, he says, “I’ll go to the Albany airport, drop my truck there and go on this job, and then come home and drive up the driveway after this crazy experience in the south of France or somewhere and just, you know, want to kiss the ground because this such an amazing place for us.”

After a wedding, he asks himself, “Am I drained or filled up?” Usually, he’s physically and emotionally drained. But then he’ll show his wife a couple of the pictures.

“Look,” he’ll say. “I made this. These people will have this forever.”

Dolan’s book, “The Perfect Imperfect,” with a foreword by Martha Stewart, is in its second edition. Signed copies are available at johndolan.com.