The Story Behind Celebrity Portraits by Jake Chessum

Natalie Portman, 2001

While photographing Portman for Nylon, Chessum took a moment to capture the actress unadorned: "For this shoot, [Natalie] wore some very beautiful clothes, but they were very obviously that season's Prada or Louis Vuitton. And I wanted to do a picture that wasn't as easily dateable; I just wanted it to be something that had no fashion content, was just a real picture of her. We went up on the roof and it was kind of windy, so the hairdresser just tied her hair back in this ponytail. She was standing; it was a hazy, sunny day; she was facing into the light. And it just looked fantastic." [via LIFE ]
 
 

Jay~Z

Jake Chessum recalls: "He had just come back from Africa with Beyoncé, literally that morning. We were at Milk Studios [in New York], and there was a big, comfy pick-up chair. He sat in that and slung his arm over his shoulder and leaned back, and he was wearing big sneaks, big jeans, huge baggy T-shirt. I said, 'God, that's a really great little picture,' but I had to go and ask his publicist, 'Can I take a picture of him now, because he looks so good?' He was totally relaxed about it, so we shot that. [But] the stylist was given a list of stuff and she brought in about 15 trunks of clothes. Very smart, very expensive suits, very dressy. . . . Before the shoot we were told we probably had about 20 minutes. That's not enough time to do anything. But I don't know whether he was so jet-lagged he wasn't able to leave, or whether he was just chilled-out -- for some reason he wanted to hang. He was there for two or three hours -- just a lot of standing, chatting, trying stuff on."

Alec Baldwin

Some quick thinking -- and a fortuitous playdate Chessum had set up for his daughter near the Hamptons location -- helped save a shoot with Alec Baldwin when the actor arrived late, then refused to go sailing as planned: "It's 105 degrees outside. [Baldwin] calls me over: 'Sit down, sit down. Umm,' he said, 'I'm not going out on the boat. It's too hot. It's 20 f---ing minutes to get out, and you have to go 2 f---ing miles an hour. . . . I'm not doing it.' It's like, What do you mean? But you can't argue with him -- he's not going to change his mind. So I'm thinking on my feet and I say, 'Okay, what about we go to my friend's pool?' He looked me up and down -- I'm pretty scruffy -- and he said, 'Your friend doesn't have a f---ing pool.' And I'm like, 'Trust me, my friend has got a pool, and it's about half a mile away from here.' So he kind of looks at me and goes, 'Yeah, all right.'"

Alec Baldwin's Swimming Buddies
"So I texted my friend, Lisa, and I asked, 'Can I bring Alec Baldwin to your house?' And she texted back: 'The answer would be yes.' We turned up and they had their whole family there because it was their hangout; it was like grandstands on the deck. Alec grabbed my daughter's friend Georgia, stood on a surfboard, and promptly fell in fully clothed in some Ralph Lauren suit. He did sharks and threw them in the air. He did 20-25 minutes, and then he got out, dried off, got in his car, and drove away. "

Bill Murray, 2004

Finding the right prop for Murray, who was promoting The Life Aquatic at the time, was a funny (and expensive) challenge, Chessum recalls: "Bill does not have a publicist or anything. He gives you a cell phone number and everything goes down through his wife or him -- whoever picks it up. So we had this [dilemma]: What are we going to do with him? He hadn't called back; we didn't know if the shoot was happening or not. Suddenly, at the very last second, Okay, it's happening, it's going to be on Sunday, Pier 59. What are we going to do? Nancy Iacoi, the Esquire photo editor, and I talked about it and came up with the idea: What if we have a fish in his mouth? Instead of a real fish, which obviously wasn't going to happen, Nancy got a prop maker to make this fish for Bill to stick in his mouth. It was a rush job. I don't know how much it cost, but it was a lot -- in the end, they paid, like, four figures for this bloody thing. We got to the shoot. He turned up Sunday morning with his son, and he couldn't have been more funny, charming, nice -- like your favorite uncle. He was a knockout. But we get to the shoot and he's like, 'Oh, what's this thing? Where'd you get this?' And Nancy said, 'Oh, God, you wouldn't believe. . . . It cost 2,000 dollars' or whatever. And he just cracked up. He said -- because he's a fisherman -- 'Babe, you could have got one of these at a bait shop for five bucks.' He thought we were the biggest idiots."

Chris Rock, 2007
Chessum recalls photographing the comedian/actor on assignment for LIFE: "He was promoting that movie I Think I Love My Wife, so we basically got 50 million props -- millions of things that were anything to do with love, Valentine's stuff, hearts. Just something to get him going, because he's one of those guys who is very private. He doesn't give a lot away, I've found; he's tricky to get to know. But he responded to the balloons. We have some pictures of him sitting around on the floor, on the sidewalk with the balloons blowing around. But at one point that one flew away, and he started chasing it. I got two or three frames, but that was the best one, the most random."

Mickey Rourke, 2008

Chessum's shoot with Rourke, for Entertainment Weekly, began with a directive from the actor's people: "I got a call from his publicist saying, 'Mickey doesn't want to talk to anybody. He really doesn't like a lot of people around. And he wants you to meet him outside of the car so you can talk to him about the shoot.' So I went down and waited on 11th Street for the car to pull up. He got out and said hi, and asked, 'You ready?' I said, 'As ready as I'm ever going to be.' And we jumped in the elevator together, went up, and everyone's ducking out of sight, hiding. He asked, 'What do you want to do?' And I told him, 'I don't want you to do anything really crazy or specific. I was hoping we could just hang out and see what you do with this space.' Because it was a cool space -- a big, old water tower with a view. He said, 'Okay, Okay. Leave it to me.' And he went into this little act. He would sit and take off his shoe, put his shoe back on. Swing his jacket around, walk about. I'd follow and make a couple of suggestions, but let him just be this character, whatever it was. He'd lost his voice to the point that I could hardly hear a word he was saying. And he was constantly wanting his lip balm. [Mimicking Rourke addressing his personal assistant] 'Where the f--- is it, Bob? Give me the lip balm.' Because his friend couldn't hear, I'd have to turn around and say, 'He wants the lip balm.' It was a slightly surreal thing."

Johnny Depp 1999

For this shoot at the Frank Lloyd Wright-designed Ennis House, the actor pulled up in a vintage Porsche and was friendly and gracious, Chessum recalls -- even after the photographer made what he calls now a "shatteringly crass" joke: "I think he [and girlfriend Vanessa Paradis] had just had a baby, [daughter Lily-Rose], and he was talking about how it's so amazing, with the baby laying there in your arms, and how they kind of stir and open their eyes and look up. And I jumped straight in: 'And say, F---! It's Johnny Depp!' And he kind of looked up at me. . . . I mean, I just couldn't resist."