Mr Chris Buck photographs the world’s most famous people – and creates the images that will be remembered.

It’s not easy being a photographer in the age of Instagram. As stars post their most human, vulnerable and IRL moments on social media with precision timing as their latest project drops, they put out less and less when they sit down to be snapped by a professional.

So, it is quite a skill to be able to capture them in a new light. Which makes Canadian photographer Mr Chris Buck’s work all the more impressive. Not only does he consistently manage to get candid moments with some of the most overexposed people in the world, he has an uncanny knack of landing them just at the right time, whether that’s when they are on the cusp of superstardom, or when their fame is at its zenith.

For instance, this shot of Mr Keanu Reeves (below), all floppy hair and untoned tum, shows him lifting his shirt and showing the toothy smile that made him. It was taken at the 1988 Toronto International Film Festival when The Matrix was more than a decade away and Bill & Ted’s Excellent Adventure was still in development. “He was the most handsome man on the planet at the time,” says Mr Buck. “Irresistible to men and women.”

His shot of Mr Ewan McGregor for Entertainment Weekly was taken while he was promoting Trainspotting in 1996. Mr Buck chose the apt location of a squat in New York. The picture of Ms Lena Dunham was taken a couple of seasons into Girls in 2014. Mr Buck was interested in her because “she had established herself as a voice really quickly. She is an amazing talent. And she does it all with flair and attitude.” Other subjects include Messrs Wes Anderson, Joaquin Pheonix and Johnny Depp.

So, how does he continue to create these moments in which stars feel comfortable enough to let him in and, in Ms Chloë Sevigny’s case, mime an act of oral sex? “It’s unconscious to a large extent,” says Mr Buck.” I want them to be comfortable enough to go there, but not too uncomfortable to say no. It’s an in-between moment. A little awkward. A bit like being on a date.”

And they do say no. Ms Dunham wouldn’t pose naked for him, despite spending much of her screen time on Girls in the nude. “She said, ‘I only do nudity when I can control it.’ Fair enough.”

He’s now put his favourite images from a 30-year career shooting for GQ, The Guardian Weekend, Time and New York magazines into a retrospective called Uneasy. The book features more than 300 images, including his earliest shots of his heroes Messrs John Lydon and John Cale, which Mr Buck took while in college. He funded the book via a Kickstarter campaign.

There are a few people he would still like to photograph, such as his fellow Canadian, the telegenic prime minister, Mr Justin Trudeau. He has photographed President Trump three times; the last time was on the campaign trail for the US election. Would he shoot him now? “Of course,” says Mr Buck. “If I only photographed people I agreed with, the book would only have 10 people in it.”

Below we hear from the photographer himself about the cult stars he persuaded to do something different for his lens.

Instagram: @the_chris_buck

“I guess this was an early sitting for Joaquin, because the magazine was so concerned about him being nervous that they wouldn’t let me take an assistant. We shot on his family’s rural property in Florida. We did a number of different setups, and it was quite relaxed and fun. He had a sweet disposition, but he did seem damaged in some way (or was I projecting?). He reminded me of a young Montgomery Clift, so I mailed him a VHS copy of A Place In The Sun as a gift. He sent me a thank-you note on the back of an alligator postcard.”

“Keanu was sitting with a reporter at a hotel rooftop lounge during the Toronto International Film Festival. I approached him and asked, ‘Can I take your picture?’ His manner was a little like that of his character in Bill & Ted’s Excellent Adventure, but sharper. ‘I don’t know why you’d want to, but sure, yeah. Let me just finish this.’ So he finished his interview, and I took him around the side of the building where the lighting was better, and we started shooting. He had a turtleneck sweater on, and I said, ‘Pull it up, like that James Dean picture.’ I was referring to Phil Stern’s iconic portrait of Dean, where he’s got his black sweater up over his mouth and nose. He pulled it up and, when he did so, I saw the scar [the result of a motorbike crash]. I said, ‘Show me your scar again,’ and he grabbed his shirt and pulled it up high, laughing, and that’s how I shot it.”

“Ewan was promoting Trainspotting, so I found a real East Village squat for us to shoot in. Only the most ill-kept rooms would do, so I had us in this space that must have been home to a drug addict. There was paraphernalia around, and the place smelled terrible. The doorway shot was set up, and I asked Ewan to lie down for it. He looked at his publicist and asked, ‘Do I have to do this?’ She said, ‘Just do it, and then we’ll leave.’”

“Especially with hip-hop, the way people tend to pose is pretty predictable, and I wanted something that was outside of that. This was just something I could do that would be a little surprising. I basically just told him, ‘I want you to stick your head into the fish tank,’ and he was like, ‘OK. You mean like this?’ The funny thing was that he put his two cents in and asked that we put a bottle of tequila in the shot. If you look through the fish tank, you can see it.”

“Yes, she’s making a face that implies a certain intimate act. At least, that’s what I inferred, since she broke into a sly smile as she came out of this look. Plus, she had just finished The Brown Bunny, a film that seems to be solely known for her depiction of this act.”

“After researching Mickey Rourke in preparation for the shoot, I swore that I would not photograph him with his little dog. It seemed like it was all I ever saw of him and, frankly, it was just too cute for my taste. But then he walked in with the dog inside his long-sleeved T-shirt, with its little head peeking out. ‘OK, I submit!’”

“Lena Dunham arrived promptly for our Guardian Weekend shoot at a Brooklyn studio, and she announced that she’d be needing some underwear. As we moved forward with the shots that we could do sans undergarment, there remained some unanswered questions: would the underwear arrive? When would it arrive? And how might it alter the shoot? Though she has a media reputation for being self-involved, it would be hard to imagine her being more gracious. For instance, complimenting people, asking them questions (celebrities aren’t usually this nice). She was also generous where it really counted – with the photography. Her genuine embrace of all that is odd and creative made working with her a photographer’s dream. She was playful, dirty and weird – everything I look for in a collaborator.”

Uneasy: Portraits 1986-2016 (Norman Stuart Publishing) by Mr Chris Buck is out now