Growing up in Toronto, he was drawn to photography because of an early obsession with popular culture. “Taking pictures was a way to indulge that interest, while pretending to work,” he says. Photography has allowed Buck to meet the kinds of people who had fascinated him—the entertainers, innovators and leaders who make the world go around. But he says he didn’t get into the business to idolize, either, and it's the friction between those two opposing instincts that makes his photographs so much fun to look at. Buck puts his own spin on things: While some portrait photographers try to reveal the real person behind the façade of celebrity, and others celebrate the glitter of fame, he finds a sidelong perspective from which to view his subjects—one he calls “glamour adjacent.”

Sometimes he does it with a dollop of humor. Other times, it's a jarring juxtaposition or an odd graphic element that sets his images askew. The results are oddly engaging, which is why the New York City-based photographer has been able to maintain a thriving 26-year career shooting for a varied roster of magazines—from Time and ESPN to New York and Texas Monthly—as well as advertising clients who appreciate his visual wit. That includes brands like Old Spice and Viagra.

His inclination for the off-kilter carries over to his personal work as well. For a dozen years, Buck has been taking the idea of the self-portrait in a new direction by photographing other people named Chris Buck. More recently, he’s been working on a portrait series about exotic dancers—except that instead of photographing the dancers, he shoots their boyfriends. “It just seemed like a more interesting idea than photographing strippers themselves,” he says.

Four Minutes and 22 Seconds With Barack Obama

To put it another way, Buck manages to get close to his portrait subjects while keeping an intriguing distance. Sometimes the distance is inferred, but it can also be quite literal, as in one of his most memorable recent images—a portrait of President Barack Obama shot for the New Republic  in 2013. In one sense, creating the photo represented the ultimate fulfillment of Buck's childhood dream of encountering the famous and influential. “It was a lot of pressure, but it felt to me that the first 25 years of my career were leading me to that moment,” he says. Typically, however, Buck decided to take an oblique view of power when he showed up at the White House.

“The morning of the shoot,” he says, “I was having breakfast with the magazine’s creative director, Dirk Barnett, and he asked if I was going to change into a suit before we went to the White House. I was pretty casually dressed, but I said, ‘Nope, this is what I’m wearing.’ And he said, ‘But you’re going to the White House to meet the president!’ And I said, ‘And the president is going to meet me.’ I was there to work, and this was another workday for me. Even though we were shooting in his office, once he walked in that room, that was my set, my studio.”

Once on set, Buck had precisely four minutes and 22 seconds with Obama. He stood the commander in chief against a simple backdrop he’d set up, but rather than shooting a traditionally framed portrait, Buck backed off to reveal the entire makeshift studio he’d constructed.

The resulting photo, an amusing wink at the reality of the political photo op, shows the leader of the free world dwarfed by the photographer's own lighting gear and stage.

Getting the Personal Work Done First

The photograph of the president was later selected for the American Photography 30 annual, along with two other images by Buck that highlight his particular way of looking at people—a stately portrait of comic actor Nick Offerman shot for Chicago magazine and a raucous photo of the executives behind Vice, the media company known for its audacious style of journalism. That picture, done on assignment for the New Yorker, was a near miss that turned out well.

“On an assignment, I usually focus on getting a good photo in the can for the client, and then I like to do something else, maybe a little edgier, just for myself,” Buck says. “But on this shoot I decided to start by shooting the picture I wanted, assuming the Vice crew would be into the idea and give me plenty of time.” Buck had constructed an elaborate set to show the Vice executives acting out their rowdy reputation in the context of corporate America. When his subjects showed up—45 minutes late—and told him to hurry because they had other things to do, he had to work fast. “I did the shot that I wanted and had almost no time to get a shot for the magazine,” Buck says. “I gave the editors everything I’d shot—my first image included—and assumed I’d never work for the New Yorker again.”

Instead, the magazine loved the photo Buck had shot for his own portfolio and ran it as a double-page spread.

For the portrait of Offerman, Buck decided to try something understated. “I’d photographed him several times before, and I knew that Nick would do almost anything for a picture,” he says. “But that’s both awesome and intimidating, because it can lead you down a path where you’re trying to think of the most outrageous ideas you can.”

Since the Offerman photo was going to be the cover of Chicago magazine’s annual fall culture guide, Buck went with a classic approach—photographing Offerman in a costume referencing a Rembrandt painting.

“Chris’s pictures are so funny, but not over-the-top,” says Chicago magazine Photography Director Megan Lovejoy Deja. “Since Nick is from Chicago, he was a natural for the cover, and Chris made the photo all about Nick’s face—his famous mustache is the central focus. But the nod to Rembrandt made it surprising.”

And it is surprise, Buck says, that makes an editorial photo meaningful.

“A lot of photographers, when they’re starting out, think only about what the client wants, and the photo ends up being directed by the magazine,” he says. “My philosophy is that it’s my job to change the magazine, to move the magazine forward into areas that it hasn’t necessarily been. It’s the duty of anyone working for a magazine, whether it’s the writing or illustration or photography, to push it. That’s also a good way to not become predictable.”