Gray suit, Dior Homme. 17 E. 57th St.; Shirt, Dunhill. 545 Madison Ave.; Tie, Giorgio Armani. 760 Madison Ave.;

Gray suit, Dior Homme. 17 E. 57th St.; Shirt, Dunhill. 545 Madison Ave.; Tie, Giorgio Armani. 760 Madison Ave.; Watch, Montblanc.
598 Madison Ave.;

Before AMC cast Jon Hamm to play Don Draper on Mad Men, his acting gigs peaked out with various smaller parts such as an 18-episode run on the series Providence, a two-episode run on CSI: Miami and a supporting role opposite his girlfriend, Jennifer Westfeldt, in the 2001 movie Kissing Jessica Stein. Three years later, it’s hard to think of contemporary culture without the impact of the runaway hit Mad Men, a show that’s become shorthand for a very specific time, place and look, the likes of which hasn’t been seen since Michael Douglas ruled Manhattan as Gordon Gekko in the original Wall Street. This fall the 39-year-old has two films out—The Town, directed by and costarring Ben Affleck, and Howl, a biopic about beat poet Allen Ginsberg—and though he’ll admit that Don Draper has changed the landscape of television and the lives and styles of many of its viewers (especially those in New York), at 8:30 on a Saturday morning before his first cup of coffee, he’d much prefer to talk about baseball and The Big Lebowski. And so we did. Eventually.

GOTHAM: At this point, does it kill you to be forced into postulating on what is means to be a man in the modern age?
It's sort of silly, the fact that we're looking to define something as nebulous and ever-changing  as a concept like modern masculinity by a fictional character like Don Draper, but I guess that vibe seems to be out in the ether.

Why do you think America was so ready for Don and Mad Men?
It debuted at the end of the George W. Bush era, so we had a hugely fractured public with crazily polarized political views, an unstable economy, artistic weirdness and huge technological advances. You can easily make the argument that those things were happening in 1960, and it resonated really loudly because of that. And it was the first show to highlight this era in terms of the look and feel—the clothing, the design. People enjoyed revisiting that stylistic vocabulary

Certainly your look is hugely influential, starting with your hair.…
My hair is an ongoing source of embarrassment. I’ve never had a good hairstyle, so the fact that my job has me in what amounts to a hair helmet is pretty great for me.

How do you think Don’s going to look come 1980?
Well, old. Honestly, Don’s kind of old now. He’s a bit of a previous-generation guy. And if anything, the ’60s were about this young generation sweeping the decisions out of the hands of the adults and putting them in the hands of the youth, and we’ve never really rebounded from that. The children basically still make all of our cultural decisions today.

How much did you know about Don when you were cast?
I really didn’t know anything except for what was in the pilot script. But once I actually got the part, [creator and executive producer] Matt [Weiner] told me Don’s crazy, elaborate backstory, and I was just like, Oh my God; it’s like Dickens! This guy’s dad got killed by a horse, he was a hobo.... When taken out of context and when done poorly, you can sort of pooh-pooh it and say it’s over-the-top or soapy, but I happen to think that it’s just rich.

Was taking a job like 30 Rock an antidote to your day job?
[Laughs] I don’t know if it’s an antidote. It’s a little daunting in many ways, because I was and remain such a fan of that show, of Tina Fey, Alec Baldwin, Tracy Morgan and Jack McBrayer. It’s super hard to come from this sort of heavy, serious drama, not being known as a funny guy, and to go there and be loose and jokey. All my scenes were with Tina, and had she been totally unavailable or weird or a comedy snob it would have been miserable, but instead it was delightful in every aspect. But it was stressful at the beginning, and I was just hoping that I wouldn’t trip on the furniture and look like a total idiot.

And filming it gives you a nice excuse to come back to New York. Do you have favorite spots to hit when you’re in town?
I have a bifurcated existence in New York. Jen and I have an apartment on the Upper West Side, and we have favorite neighborhood spots up there like Gennaro on 92nd and Amsterdam, which is absolutely delicious.

And the other half of your New York existence?
We have probably 30 friends that live within a five-minute walk of the 14th Street 2/3 subway station, which is great for us. There’s a place near [costar John] Slattery that’s fantastic, Giorgione, and a block away there’s the Ear Inn, too. Everyone’s default bar in the West Village seems to be Dublin 6. But also Minetta Tavern is amazing.

Ever self-conscious about going to places that feel too Mad Men?
It’s funny, I was looking at an old copy of The New Yorker from 1960 on set, and in there was an ad for Keens Steakhouse, boasting “60 Years of Excellent Service!” This ad is 50 years old, and Keens is still serving. Slattery and Matt and I and some folks from the network had a pretty wet lunch at Keens after Season 2 ended, and it was great. I don’t know how people work after lunches like that, but what’s wrong with having a giant steak and creamed spinach at lunch, and a dirty martini?

This month you’re also appearing as an FBI agent in the Boston-set crime drama The Town. As a St. Louis native, how hospitable did you find the city?
I think Bostonians have a soft spot in their heart for St. Louisans because we essentially gave them their World Series. They don’t quite have the same vitriol that they’ve reserved for New Yorkers. We did a lot of shooting in and around Fenway Park, and it was really amazing to be in that place. I’m a huge baseball fan—I still play baseball—and if I walk past a baseball game in a park, I’ll sit and watch. I just love the game.

Who do you play baseball with?
Baseball is one of those things that requires a very specific skill set, and it gets harder and harder the older you get to find people who have those specific skills and want to put their knees, backs, elbows and shoulders in mortal danger every Sunday. But weirdly enough, I got cold-called, or whatever the e-mail version of cold-called is, by Ben Affleck’s brother, Casey, who was putting together a team and asked if I was interested. I was like, Absolutely! I have no fear of looking like an idiot.

Next up for you is Howl, in which you play a lawyer defending the poet Allen Ginsberg on obscenity charges.
It’s an interesting, bizarre film, very much an art film. It’s basically a biopic of Ginsberg’s poem Howl, and I was honored that they asked me to be part of it. It wasn’t a particularly risky part for me—a dude in a suit in the ’50s—but the excitement for me was getting to be in a courtroom and saying these things that came directly from court transcripts. One of the reasons I wanted to become an actor is because I read Inherit the Wind, then I saw Spencer Tracy in it, and I was like, That’s not how I thought it was going to be. It was a total transformation.

So Spencer Tracy was an acting idol. Who else?
I’ve seen everything Jeff Bridges has been in. I got the chance to meet him during this recent round of awards insanity, and he’d just won the Academy Award for Crazy Heart. I’ve never really been speechless, and I made an idiot of myself—I stood there with my hand out and I could not talk. I mean come on! He was “The Dude” [in The Big Lebowski]! There’s no more indelible character than that, I’m sorry.

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