For three decades, Chris Buck has been making curious, quirky and revealing portraits. He recently self-published a retrospective collection titled Uneasy, a 400-page book comprising 338 portraits shot between 1986 and 2016. With his offbeat humor and counter-intuitive sensibility, Buck pokes and prods at self-aggrandizing cultures of celebrity and politics. His quick reflexes are on full display. Celebrities ham it up in front of his camera at their own peril. He has no qualms about catching his subjects a little—and occasionally a lot—off guard. When rapper and DJ Timbaland fell asleep on set, for instance, Buck made a portrait that more deferential photographers wouldn’t have dared to make. Buck also manages to be brazen and disarming at the same time, so his subjects do outlandish things for him—sometimes on their own initiative, and occasionally over the strenuous objections of their publicists. “No, no, no, we can’t do this!” said Kevin Smith’s publicist, to no avail. Moby’s publicist was also evidently overruled, or not present.

Among the photographs in Uneasy are several iconic portraits, including Buck’s 2005 photographs of Steve Martin and Steve Carell. But so many of Buck’s portraits stand out, and the collection is notable for its range and variety. He reveals his process through amusing and informative anecdotes about more than 100 of the portraits. Buck plans his shoots, showing up with props and requests, but he also thinks on his feet and leaves things open to chance. Of his portrait of Billy Bob Thornton turning his back to the camera to pee on Buck’s seamless backdrop, the photographer says, “When I present ideas that are a little out of left field like this, I don’t over explain, I just ask—because the more you explain, the more likely they are to overthink it and say no. You want to present an idea like this as if it’s very reasonable and normal.” About his portrait of Jerry Stiller riding a horse, Buck says, “In trying to make funny pictures, I often try to think of what I cannot picture this person doing.”

Buck’s photographs are ultimately distinguished by his singular instincts and interactions with his subjects. He gets people to reveal their vulnerability, in part because he’s unafraid to reveal his own. (He seems to delight in recounting some of his most embarrassing moments on set.) Buck also has a lot of moxie, and a keen sense of just how far he can push things. When Barack Obama arrived on set chewing gum, Buck mock-scolded him. During the shoot, he directed the president to give a sidelong look at the camera. Buck recounts: “[Obama] said, ‘I don’t do that.’ I shot anyway. I felt like I’d spent the first 25 years of my career preparing to defy a sitting president to get the shot that I wanted.” —David Walker

On Wednesday, May 17, Chris Buck discusses Uneasy in an event at the New York Film Academy.

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