How did you get the part of Wilhelm Grimm?
I read it and they said, "This is a Terry Gilliam movie and you have an offer to play this role." I went, "Why? How?" Really. I couldn't believe it. And the first time that I met Terry, I said, "Why isn't Johnny Depp doing this?" And Terry goes, "The studio wouldn't make it with Johnny. You're my second choice." Then, of course, Pirates of the Caribbean came out. Now (Miramax chief) Bob Weinstein is like, "I can't f–ing believe that we got Damon and not Depp."
What was the greatest misconception you had about Heath Ledger?
I thought that he'd be a better kisser. I wasn't that disappointed. Just a little.
What was it like working with Martin Scorsese on The Departed?
It was great. I was pinching myself. I mean, this kind of run of work for me – between guys like Terry Gilliam and Scorsese and (Robert) De Niro (who is currently directing Damon in The Good Shepherd) – it's just like, that's it. If I screw this up, that's it.
You have an apartment in New York City. Do you wear your Boston Red Sox cap there?
Yeah. Well, before (the Red Sox beat the Yankees in the 2004 American League Championship Series), what was great is that people would kind of give you that look of, "Oh, look. A Boston hat." Now it's like, "Hey, f– you. We're going to beat you." It's a totally new thing. They were the gracious winners and now they're so totally pissed off.
Will there be another season of your Bravo reality show with Ben Affleck, Project Greenlight?
We don't know yet. No one tunes in to watch it because no one knew about it, even though I thought this season was terrific. I mean, we got nominated for another Emmy. (But) I think that Bravo's argument is that, "Look, there's a certain number that's so low in the ratings that it doesn't matter if a show is good. You can't keep it on the air." That's like a boulder we've been pushing up a mountain for five years now.
Why didn't you go to Ben's June 28 wedding to Jennifer Garner?
Well, I mean, he just wanted to get it done, which I really understand. They had to do it quickly and quietly. I mean, I got a phone call.
Any pressure for you to tie the knot?
No. All of our friends aren't like, "Four of us are married now, so the other three better do it." We don't really think of it that way because each case is different.
Is Ben excited about being a dad?
Yeah. Yeah. I think he's going to be great.