It’s evident that Josh Brolin possesses the star appeal and refinement most men need to carry out careers as leading men. What’s surprising is that he doesn’t necessarily want to be cast as a macho jack-of-all-trades. Brolin prefers disappearing into characters, most of whom are simultaneously pathetic and endearing anti-heroes. In You Will Meet a Tall Dark Stranger, Woody Allen’s latest film, Brolin plays Roy, a burnt-out writer trying to secure a living while dealing with absurd in-laws and his desire to be with a beautiful muse across the street.

One reporter at a roundtable interview during the Toronto International Film Festival asks, “Do you have a checklist now of directors to work with? It’s a pretty eclectic lot.”

“I would like to think I have a checklist and that I have the power to choose but I say yes if they ask me. So I guess it’s my choice ultimately but I’m so moved and it’s so otherworldly to me that these people are interested in working with me. And then they become friends. Woody became a friend during that movie, and the Coens have become very good friends.”

Brolin has worked with Allen before, but never in such a major capacity. The last time he teamed up with the famed director was in Melinda and Melinda in which he held a minor role as a dentist. Still, when looking over Brolin’s past efforts, one might never guess a Woody Allen film would be in the cards.
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“Woody and I said to one another, ‘I could never possibly pretend to be you, nor could you possibly pretend to be me. If there are two more opposite people on this planet, it’s me and Woody Allen’…. I love language. I think it’s an art and Woody has created a vernacular that’s pretty amazing. And Woody would say to me, ‘Hey man, just make it your own,’ and I would do a take and he’d say ‘Um, you changed it. You said cannot but it says can’t.’ I said, ‘You’re not serious are you?’ And he said, ‘Yeah, you broke the contraction.’ I said, “I know, you told me to make it my own.’ And he said, ‘I know, but the line says can’t.’ And I thought this is just insane.”

While Brolin would like to think that he has nothing in common with Roy’s character, he likes delving into psyches different from his own. “I don’t like Roy at all,” says Brolin. “But I do like that in his desperation, need for fame, acceptance, and notoriety, that there’s this pathetic soft spot in him. He’s like a little kid that just wants to get noticed.”

Another reporter, who just happens to be sporting a bike helmet with a video camera attached to his head says, “I was ironically reading a magazine today and your wife [Diane Lane] was talking about wanting to get a boob job and saying that you always talk her out of it.”

“Dude, you are weird, you really are. I’ll remember you forever,” replies Brolin. “First of all, that’s not true. Second of all, she’s like any other vulnerable actress in Hollywood who worries about there being some ceiling to their career. I can’t imagine a ceiling to my wife’s career. I think she’s like Gena Rowlands, she’ll just be around forever…. If you look at my wife’s boobs, you’ll see that she doesn’t need a boob job. I know that’s going to be everywhere now that I’ve said it.”

The same reporter with headgear continues with his amusing questions: “Would you rather get first dibs or the last laugh?”

“First dibs because the last laugh has a negative connotation for me. Like ‘na na na na na.’ I don’t like those people.”

“Would you rather be a dog named killer or a cat named fluffy?”

Brolin is taken aback. “You mean am I straight or am I gay? Dude, I’m going to help you come up with those and we’ll do them together with other people.”

I finally squeeze a question in at the end about his upcoming film Wall Street: Money Never Sleeps, where Brolin is once more under the direction of Oliver Stone.

“I read that you’re an octave, sorry active, stock trader.”

“I like octave better. Seriously that’s not a screw up,” states Brolin.

“How do you think your trading experience helped you with your role in Wall Street: Money Never Sleeps?”

“I was a personal trader. I made my money doing that when I was doing Woody Allen type films and not making a lot of money. But it helped me with the vocabulary and allowed me to meet with these guys and ask somewhat intelligent questions. World finance is a different planet… But it’s very interesting to me. The tough thing when talking about Wall Street is I try to keep it behavioural and emotional because I could talk about stock trading forever and I can see the film glaze over your eyes when I talk about it. I think it’s really fascinating and nobody else really does.”

You Will Meet a Tall Dark Stranger opens in theatres on Friday.