Suede jacket, John Varvatos ($2,198). Neiman Marcus, Copley Place, 617-536-3660. t-shirt, James Perse ($85). 17 Arlington St., 617-369 -4570. Jeans, A.P.C. ($210). Barneys New York, Copley Place, 617-385-3300.

That skeptical attitude toward success, says Slattery, was cultivated in a large middle-class household—two boys and four girls—led by his father, Jack, who was a leather merchant, and his mother, Joan, now a retired CPA. While the actor feels he acquired his "stubbornness" in part from his mother, he accrued a solid set of values, including a strong work ethic, from his father. "We had to do chores and take jobs—I was caddying by the time I was 10 and later worked in a gas station—but my father never really pushed us at anything, never stressed over it," Slattery says. What the family did stress over was the fate of their beloved sports teams, especially the Red Sox, whose fate they assiduously followed. His mother's cousin was married to Jack Rogers, the Red Sox's traveling secretary at the time, and the family enjoyed many perks at Fenway Park.

"We'd take the Rattler [the trolley] into town for almost every home game," Slattery says, adding that for sheer drama nothing beats observing world-class athletes in competition. "It's so heightened, so intense," he says. "It's do-or-die time, and sometimes you end up on the short end of the stick." There was far less at stake in the neighborhood games that were a staple of Slattery's youth and which inspired momentary dreams of baseball glory. "The older I got the more apparent it became that it wasn't going to happen," he says. "I was never a star, but I could play well enough to have fun at most anything."

Slattery attended all-boys St. Sebastian's School in Newton, his father's alma mater. Armed with a healthy skepticism toward authority, he and his buddies enjoyed wreaking havoc at the school. "We turned it into a zoo," he says. It was during his cut-up days at St. Sebastian's that Slattery discovered the appeal of acting. At night he would channel surf and stop at scenes that hooked his imagination, like those from I, Claudius, the BBC TV miniseries starring Derek Jacobi about the machinations of lust and power in ancient Rome. "The production values were cheap, but the acting was so good that I would be riveted for hours," he says.

It dawned on Slattery that he might take a flyer on an acting career, and after graduating with a fine arts degree from The Catholic University of America in 1984, he headed to New York. "My father said, ‘Give it a couple of years,' but I never put a time limit on it," he says. "I had no plan B." His ascent was incremental, marked by the insecurity of where the next job would come from but also buoyed by growing critical acclaim in such plays as Terrence McNally's The Lisbon Traviata and Richard Greenberg's The Extra Man, Night and Her Stars, and Three Days of Rain. It was in the latter 1997 production, opposite Patricia Clarkson and Bradley Whitford, that Slattery earned the best reviews of his career, as "a taciturn architect" whom he played with a quiet, deeply wounded intensity.

Featured Broadway roles were also in the mix, including Neil Simon's Laughter on the 23rd Floor and a 2000 revival of Harold Pinter's Betrayal opposite Juliette Binoche and Liev Schreiber. With a slew of good notices and numerous offers for featured parts in film and TV, Slattery seemed to be on a career arc that commanded critical acclaim and respect—but not much money or fame. Then, in 2006, Rabbit Hole changed his life. Matthew Weiner, Mad Men's creator and executive producer, saw him in the play. Shortly after catching the performance, Weiner called Slattery to audition. What appealed to the producers was how he managed to bring a wry and baffled masculinity to the Sterling role that makes the character sympathetic, despite his overt selfishness and sexism. "I like Roger," says Slattery of his Mad Men alter ego. "He may say and do things that I find abhorrent, but I understand him. We are all trapped, to some extent, by our choices and the consequences of those choices."

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