We sent Contributing Editor Stephen Rebello, who last interviewed James Franco for Playboy, to talk with Damon in Manhattan. He reports: “I hadn’t seen Matt Damon since we last talked for Playboy in Chicago in 2004. Knowing he can be friendly but dodgy about personal stuff in interviews, I secretly hoped our suite would be stocked with a supply of tall cold beers as it was last time. I needn’t have worried. This time Damon, looking fit and 15 years younger than his 42 years, was much more open. The same appears to be happening on-screen. In a couple of his new movies, beneath Damon’s charm and likability is a new rawness, a vulnerability—the kind that portends an even longer, rewarding career. In conversation he was funny, smart, impassioned and about as ‘regular’ a world-class movie star as one could ever hope to know.”
PLAYBOY: What else scares you?
DAMON: I learned that I am afraid of heights. When I was doing Syriana, they arranged for my wife, Lucy, and me to go up to watch the sunset over the Arabian Peninsula from the top of that seven-star Dubai hotel that’s shaped like a sail, the Burj Al Arab. So we go to the very top—60 stories or something—we’re given champagne, and we go, “Oh my God, this is great.” But as I started to walk toward the edge, my legs locked up. I was absolutely frozen. I completely jumped my neocortex and went straight to this primal, full lizard-brain fear state. Lucy was walking all around the edge, while I was about to collapse from fear. She thought it was hysterical.
PLAYBOY: Has being a husband and father made you more aware of your vulnerability?
DAMON: I don’t know, but Lucy and the girls can definitely bring me to my knees. They just know. My wife gives me shit because it’s harder for me to discipline my girls, probably because they’re girls. With boys, I could relate more and it would probably be easier. Growing up, girls are so mysterious to us. Even as a grown man, they remain mysterious.
PLAYBOY: What personal traits of yours do you hope your kids don’t inherit?
DAMON: My kids came into the world with a kind of hyper obsessiveness and stubbornness that I know I have. I’ve always been competitive. I used to be out-of-control competitive, like when I was playing games, maybe because I grew up with my brother, Kyle, who is three years older. I was always smaller, and it was harder for me to win.
PLAYBOY: You met [Lucy] 10 years ago. Why is this relationship better than the others?
DAMON: This is the first relationship I’ve had that wasn’t like work to be in. I never knew it could be like this. There’s always stuff you can work on, of course, but being married and having kids, for me, there’s a lot of romance, but it’s a much bigger endeavor with a lot of nuts-and-bolts problem-solving you have to do together. It’s like building a company.
PLAYBOY: Are you good at turning up the sensuality and romance with extravagant romantic gestures?
DAMON: No, I’m shitty at that. I wish I were better because my wife deserves somebody who surprises her with a gift or flowers or some wonderful idea. I’ve never been good at that, and she’s really good at it, which makes me feel even more like shit.
“Just this morning, the original script supervisor on the film, it was his first job, he came up to me and said, ‘Thank you for giving me back my memory. That’s the Hitch and Alma I remember.’” Getting emotional, Rebello adds, “It’s a great responsibility.” He tells of a bit of advice recently given to him by a well-known actor. “Matt Damon, a really great guy, told me recently, ‘Movies need time, air, a chance to grow and get under your skin, or not.’ I agree with that.”
Tavis: Can you see that, when you see yourself on screen? Ooh, I was so bad then?
Damon: Yeah, I think -
Tavis: Compared to where you -
Damon: – actors can be hard on themselves and choices that I made in a scene or choices that I might have been talked into that I wouldn’t be now, or things that I couldn’t connect to because they hadn’t really happened to me yet, they weren’t real enough for me, and as much as I tried I couldn’t quite – I was pushing too hard to get there. I think you get older and somebody tells you to be sad, it’s not a long journey for you. You’ve been sad. Someone tells you to feel joy, and it’s not a big journey for you. You’ve felt joy. Those things are, I think, more accessible to – at least they are to me, as an older guy.
Tavis: When you come back on this program 20, 25 years from now and you look back on the last couple decades of your career, I’m going to ask you again how things are developing for you. So let me ask in advance of that conversation 20 years from now, where do you want to take this the rest of the way? Where do you – in the long run?
Damon: I want to keep doing what I’m doing and keep working with the caliber of people that I’m able to work with. I want to direct, I want to keep writing. I want to make movies that say the things that I want to say. I want to be on the right side of history, and I want my kids to be proud of me.
John usually has his laptop, and we jump around the room gesturing at each other and he writes stuff down," said Damon during a conversation with Krasinski, whom he credits with shepherding the project through. "It's actually the way Ben and I did it. Ben and John are the two funniest guys I know, and it ends up that we just laugh for eight hours straight and at the end we have a few scenes that we really like."
Krasinski would crisscross North America, meeting up with Damon on weekends in Vancouver, Canada, while Damon was shooting "Elysium," or in New York when the married father of four was back home doting on his household full of women.
"We wrote in the middle of barbecues, pizza time. I was a villain for a month and a half, the dude that was taking their dad away," said Krasinski, 33, whose wife, Emily Blunt, starred opposite Damon in "The Adjustment Bureau." That's how the men met.
"John is like a supercomputer. His mind is fast. And I go in real time. I read at the speed in which I talk," said Damon. "John would spit out all these ideas, and it would literally put me into brain freeze, where I would just sit there."
Which in turn would throw Krasinski into bouts of insecurity seeing Damon's stony reaction to his ideas. "I thought he hated me and wanted me to leave."
That is until Damon's wife unlocked the secret to that blank stare. "She said, 'You know how Matt works? Before bed, I'll say we've got to do this, pick this kid up, do this with this person, and he would just stare at me and I'd get really furious,'" relayed Krasinski.
"I'm just trying to make sure I can do everything she says," Damon jumped in.
"The moment she told me that, the light bulb went off," Krasinksi said. "The second half of [writing] was so much easier. I didn't slow down, but I'd wait. I'd go watch a half hour of television. Then I'd come back and Matt would say, 'Oh, I got it. I like it.'"
"Big Stars, Big Giving" is CNN’s special series that shines the spotlight on celebrities and the causes they support. In an American Morning original series, “Big Stars, Big Giving,” Alina Cho looks at celebrity philanthropy and how big stars can make a big impact. Through one-on-one interviews with Elton John, Ben Stiller, Madonna, Martha Stewart and Richard Branson, she shares what causes have become their passion, and how others can get involved. Gary White and Matt Damon, Co-Founders of Water.org are slated for 2012’s holiday special.
Matt Damon in Promised Land (Focus Features) - It's hard to believe that in any year, Matt Damon might be considered an "underdog." His new movie is probably his smallest and most low-profile film, but it's also his first movie since Good Will Hunting in which he co-wrote the script and tailoring the dialogue to his character (or vice versa) which produces absolutely remarkable results. The way he sells his character Steve Butler, a salesman for a corrupt natural gas company, and actually has the audience rooting for him is quite a testament to Damon's skillful performance.