But even character roles didn’t add up to a living, so Brolin turned seriously to day-trading stocks to earn his money. In 2006, he started the website MarketProbability.com and began pitching it on CNBC. “I’d be really disciplined,” he says. “I’d have my stop, my target, and even if the stock was going up, I’d get out. The minute you allow greed to take over, that’s it, man.”
As often happens, as soon as Brolin began caring less about acting, the big parts started coming. In 2007, in addition to No Country for Old Men, he played a sinister doctor in Robert Rodriguez’s half of Grindhouse and a sadistic detective in American Gangster. He followed those with 2008’s Milk (which earned him an Oscar nomination for Best Supporting Actor) and Oliver Stone’s W., starring as our former president.
In the Wall Street sequel, he not only got to reunite with Stone, but got to use his investing life as motivation. In one scene, his frustrated character—the head of a Goldman Sachs–style investment company—breaks a “Goya” painting over a chair. Stone left the rest on the cutting-room floor: “I sat down in the chair and started crying. And then I thought, Ooh, I can break that painting some more,” says Brolin, still amused at the lengths he’ll go. Eventually, he “smashed the painting into a ball and stuffed it in my mouth.”
Brolin and I are in the elevator headed up to his hotel room. We’re going to act like Wall Streeters—or tourists—by hitting golf balls at Chelsea Piers. But first he has to change his shirt. “Why do elevators always smell like butt?” he says, pressing his nose into the fabric of the back wall. In his room, Brolin strips off his shirt to reveal a startlingly hairless torso. “Is this uncomfortable for you?” he asks.
At the Piers we have to wait our turn. Brolin tells me that he and his wife, actress Diane Lane, travel often to Ireland. “We were going to get married at the Cliffs of Moher,” he says, “but it was too expensive—getting everybody there.” Instead, they married on their central-California ranch. Although Lane appears in the film Secretariat this fall, she’s been keeping a lower profile. “She doesn’t work as much as I do,” he says. “She doesn’t want to.”
Brolin, who used to golf for hours at a time, hasn’t swung a club in three years. “I stick out like a sore thumb,” he says. “My arms are too short. I look like a gorilla.” After a few slices, he’s hitting them onto the green and giving me constructive criticism. “You swing like my old man,” says Brolin, whose father (does it need saying?) is married to Barbra Streisand. Those must be some family outings in L.A. “We have a couple of great restaurants that not only would nobody ever suspect,” he says, “you wouldn’t want to go to in the first place.”
Despite a steady stream of unpretentious references to Sean’s birthday party and e-mailing Owen, Brolin is most comfortable as a Hollywood outsider, which is one of the reasons he loves working with Joel and Ethan Coen. In 2012, he’ll come back to New York to do four one-act plays with Ethan; one of them is based on a journal Brolin kept while shooting No Country. “You work with Oliver, and he’s got five different editors all piecing the thing together at once,” he says. “He’s a different kind of master. The Coens are in this shitty little room with half a window doing it all very intimate and efficient.”
In December, Brolin stars in their remake of True Grit, playing a bad man on the run, this time from Jeff Bridges, who is reprising John Wayne’s role as Rooster Cogburn. During rehearsal, Brolin tried to come up with a voice for his character. “I was talking like this,” he says, doing Texas redneck. “I go to Joel and Ethan, ‘It’s not working, right?’ And they go, ‘Nah.’ ” Brolin clenches his fists and raises his arms to connote frustration. He’s funniest when he’s emotionally distressed, and that can happen a lot in rehearsal. “I get really weird. I’ll be like, to the other actor, ‘Can you get on all fours, and I’ll ride you? Be a bull and we’ll do the scene like that, see what happens?’ ” He’s serious. This is how he works. “So out of sheer panic and fear suddenly this voice came out,” he says, in a slurry marble-mouthed drawl. “And Joel went, ‘Oooh!’ ”
Brolin explains that putting himself in a position of “absolute, total humiliation is what acting is. Out of that can come interesting moments.” And no one, I say, is having a more interesting moment than he is. “That’s really queer,” Brolin tells me. Then he moves in for the bro hug.