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Hamm admits he's anything but impeccable—a little rumpled, in fact—preferring shorts and flip-flops to Draper's slim-fit attire. Quite unlike his inscrutably promiscuous character, Hamm, 38, is in an 11-year committed relationship. He likes silly movies, and his favorite night out is a night in with the girlfriend (actress Jennifer Westfeldt) and the dog. He freely admits to a geeky side. "At my last job, I had an Xbox in my trailer," he says. "I like Halo. And now I have a Wii." Despite Hamm's relaxed and playful nature, there is a bond between the dashing, troubled Don and the real-life Jon. "I lost both of my parents at a relatively young age and bounced around various families and homes and friends and groups for quite a while," he explains. "If there's any connection between Don Draper and me, it's understanding that where you come from isn't necessarily as important as where you are."
Q. Your mother raised you single-handedly until you were ten, when she was diagnosed with stomach cancer. She died shortly afterward.
A. Losing my mother was very traumatic. I don't know if I'll ever get over it. And now I'm older than my mom was when she died, which is pretty strange. She died when she was 35.
Q. You went to live with your father after that.
A. He was a salesman and only in his early 60s when he died [of complications from diabetes]. I was 20. I miss him every day. He had a wild streak. He was funny, larger than life, and sad. He's probably in my performance more than I know.
Q. Were you drawn to theater at a very young age?
A. I started acting in grade school and kept returning to it in high school and college. Theater departments are usually a big collection of orphans and screwups—sort of lost tribes—and I found kinship there. When I started thinking about what to do with the rest of my life, acting was the only thing I kept coming back to.
Q. What's something you took away from those early experiences?
A. After I graduated from the University of Missouri, I was a teacher at my old high school in St. Louis. My friend and mentor [teacher Wayne Salomon] had on his desk a Samuel Beckett quote, which has helped more than anything in my career: "Try again. Fail again. Fail better." That's been a mantra of mine. If you can learn to fail, then you can probably get to where you want to be.
Q. What's the best job you never got?
A. At one point, I auditioned for the role of Jack Donaghy on 30 Rock. Alec Baldwin had decided he wasn't going to do it, but my only thought was, Why isn't he doing this role? In my mind, he was the perfect guy for it—and history has proved that! [Hamm went on to do a hilarious turn as Tina Fey's self-deluded boyfriend in three episodes of 30 Rock.]
Q. What's the strangest showbiz encounter you've had to date?
A. I did Live! with Regis and Kelly, and I had never met Regis in my life. He came up to me after the show and said that his wife, Joy, really liked Mad Men and asked if I would go back to his apartment [to meet her]. So we walked across the street in midtown Manhattan, he knocked on the door, and I stood there when she opened it. Then he took pictures of us with a disposable camera.
Q. What have you learned in your 38 years?
A. There is no one answer to happiness, despite what advertising or politics or entertainment tells you. Everybody has a different definition. The main thing is to [stay true to] your own happiness. To say, Okay, this is what I feel, this is what I think is important, and this is what I am going to pursue. Oh, and while you're pursuing your happiness, don't hurt anyone along the way.
Q. You seem very well adjusted for a Hollywood guy. What's your secret?
A. I have a low-impact way of approaching life. I don't mind heights. I love flying. Bugs don't freak me out. If you're worried about something like, say, hair in your food, it ain't the hair that's going to kill you—it's the worry.
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