From Vanity Fair:
When did you start acting? Were you pretty young?
You know, kind of. My first acting job, so the story goes, was in first grade. I was picked by my teacher to be Winnie the Pooh in our first-grade production of Winnie the Pooh—back when, you know, public school programs still had things like productions of Winnie the Pooh, and music programs and recess and things like that.
Jumping ahead a bit, or a lot, what was your first acting job after you moved to L.A.?
The first job I got was a one-episode thing on Providence where I played this sort of bartender. It was a Halloween party and I had a costume. I dressed up as Zorro. I was sort of a…
A love interest?
Yeah, for the younger sister. But what I didn’t know was that the star of the show [Melina Kanakaredes] had gotten pregnant and they were running out of lenses to shoot her with and things for her to hold in front of her. So they had to kind of beef up everybody’s storyline, and I was available. They ended up bringing my guy back for 17 or 18 more episodes. And after that, I got a little part in a movie and another couple of little parts in TV shows and pilots and this and that and the other. And I was able to, about a year after that, quit my day job and focus on it full time.
What was the day job?
Waiting tables. I mean, I’ve probably been a waiter longer than I’ve really been anything else. Or I’m probably coming up on even. But barely. I quit waiting tables when I was 29. [He’s currently 38.]
Tell me about getting cast on Mad Men.
I had a horrible pilot season that year and one of the last ones to come down the pike was Mad Men. I looked at it and I was like, AMC? They don’t even make television shows—what is this going to be? But the script was really interesting, and we did it. And as I’ve said many, many times before, I was on the bottom of everybody’s list. Like, I started at the very bottom. But to Matt Weiner’s great credit, he was very tenacious in fighting for me.
Tell me about your take on Don. One thing that’s interesting to me is that while on the surface it might look like he’s amoral, he really does have a moral code—it’s just complicated.
You know, as much as Don makes bad decisions and is sort of dubious in his motivations a lot of times, he does have a moral center that is specific and real. He’s fiercely loyal to people that he feels deserve it and less so to people that don’t. He’s confused and he’s confusing, and yet, he has to project this sort of ultimate confidence. And those juxtapositions and dichotomies, I think, are what make the show a lot different than most. You always know Jack Bauer’s going to do the right thing. He’ll kill a couple of guys, but they were bad guys, all of them—they deserved it. There’s really never any gray area. He’s a superhero. And that’s taking nothing away from that show or Kiefer’s performance. He’s amazing. The fact that he does that day in and day out for 24 episodes a year, for six seasons now—the guy deserves a fucking medal. I mean, I don’t know how he stands up. But ours is a different sort of way of telling a story. And I like playing this character. I like going to work. I like telling the story. And, you know, we don’t get a lot of advance warning. Matt doesn’t tell us what’s happening [with the story going forward]. He’s very secretive. But I kind of like not knowing.
Does it help in the performance, not knowing where the story is ultimately going?
Sure. I mean, no one knows where you’re going in life. We could walk out the door, get hit by a car tomorrow. But every week we get to read another chapter of this awesome story. So it’s exciting.
When you took the part, did you do any research into the period or into advertising?
The only real research I did was books, literature, film from that era. And I had a kind of a working knowledge of what that guy was like through my father, who was a businessman. We had a family trucking company based in St. Louis from the turn of the century. And I would look at pictures of my dad in 1950, 1960. He was a big guy. And [the image]was that kind of stuff. I mean, it was whatever club he belonged to—Missouri Athletic Club in St. Louis—and the Shriners and suits and all the gear and all the cufflinks. My dad had jewelry boxes full of watches and cufflinks and just like this detritus.