BROTHERS IN ARMS Josh Brolin and Terry Richardson chatting before their shoot at Milk Studios in Hollywood. DAVID SWANSON

When Josh Brolin arrived at the studio in Los Angeles to work with Terry Richardson on the pictures in this issue, it was like a family reunion between two long-lost brothers, even though they'd never met. Both had grown up around L.A., the sons of famous fathers in the fields they eventually chose to pursue. And both had played in California punk bands in the '80s. "We had a lot to talk about and a lot to reminisce about," Brolin says.

Known for his portrayals of villains in movies like "No Country for Old Men," "American Gangster" and "Milk," Brolin gets a chance this season to play the hero, both in "Men in Black 3," alongside Will Smith, and in "The Gangster Squad," a period piece about the mob's early days in L.A., which co-stars Ryan Gosling, Emma Stone and Sean Penn. But even for "The Gangster Squad," he was approached about playing the heavy: Mickey Cohen, the notorious Jewish mafia kingpin. "I did a bunch of makeup tests," Brolin says. "Finally, at the end of the day, I was like: 5-foot-5 Brooklyn Jew. I'm good, but I'm not that good." It was Brolin who convinced Penn, an old friend, to take the part.

Photos: A Path to Stardom

His father and stepmother, Barbra Streisand LESTER COHEN/WIREIMAGE

Brolin has traveled his own path to stardom, earning a Best Supporting Actor Oscar nomination for "Milk" after years of film and TV work. But his Hollywood connections run deep: His father is James Brolin, well known for his TV work in the '70s and '80s, and now married to Barbra Streisand. His wife of seven years is Diane Lane, an Oscar nominee herself. Even Brolin's daughter from his first marriage, Eden, is currently studying acting in New York City. "She has a lot more talent than my dad and myself, that's for sure," he says. He compares her talent to his wife's, calling it "intrinsic" and downplaying his own as "more cultivated."

For our shoot, Richardson and stylist George Cortina kept things pared down and slightly rugged, reflecting Brolin's own style. "I'm a jeans-and-flannel-shirt kind of guy," he says. "Thank God I have a wife to help keep me clean. If it were up to me, I'd probably wear the same thing all week long. And she'll go, 'Take that off,' and then she grabs another shirt and hands me the deodorant." And Brolin was impressed by Richardson's creativity. "He's an incredible guy," he says. "I had a great time with him. Which allowed me to have some fun." The results speak for themselves.