While entertaining us for the last seven years as the womanizing/hard-drinking/LSD-taking ad exec Roger Sterling on Mad Men, John Slattery has been plugging away on the side with a passion project, his feature directorial debut God's Pocket, in theaters now. An adaptation of the Peter Dexter novel of the same name, the darkly comic tale set in 1970s blue-collar South Philadelphia centers on Mickey Scarpato, a schlub strapped for cash who tries every con in the book to give his stepson a proper funeral. At this year's Sundance Film Festival, Slattery premiered the film with Philip Seymour Hoffman in the Mickey role and Christina Hendricks, John Turturro, and Richard Jenkins rounding out the cast. Since then the film has become best known as one of Hoffman's final performances (and a strong one at that) following his accidental drug overdone in early February.

As the first half of Mad Men's final season winds down, we caught up with Slattery about what interested him in God's Pocket, coping with the loss of Hoffman, and what he feels is Roger Sterling's most madcap moment.

ESQURE.COM: I'm assuming the neighborhood of God's Pocket is not similar to where you grew up outside of Boston, but what was it about the book that grabbed your attention?

JOHN SLATTERY: It's similar in character. Not physically, it wasn't as much of a struggle for me as it probably is for the people of God's Pocket, but I had a lot of cousins and uncles who had similar sensibilities, which was concise, funny, not afraid to turn a phrase or at least threaten to pop somebody if they didn't get what they wanted. But what really attracted me was the tone of the book. The book was very visual, the description of the place and the people. It really was the people, people who have known each other forever, there's an intimacy and a lack of pretension. The opening narration describes how these people have seen each other naked, they've stolen from each other, and then lent money to the people they stole from. So that's what I liked about it, there was a cut-to-the-chase sense of the place.

ESQ: The neighborhood is very much a character in the film. In South Philly there's no such section called God's Pocket, so was it a challenge to find the right location?

JS: It was hard to find initially. I scouted Philly in a section that's called The Devil's Pocket, but like a lot of neighborhoods it's not the same anymore. I had certain requirements. I needed a bar and a house that you could see in the same shot. It needed to be a certain type of neighborhood and we saw places in the Bronx but nothing you could shoot with any distance because if you're two blocks away, then a McDonald's or a Chase Bank is in the shot. Then we rolled into Yonkers on the second half of one day of scouting and there was just a section where the telephone wires are hanging a certain way, and you could shoot for blocks. The flower shot, funeral home, meatpacking place, it was all right there within about a mile of each other. It was like a backlot.

ESQ: Did you want input from author Peter Dexter while you wrote the screenplay?

JS: So I read the book about ten years ago and I tried to get the rights but was told they were owned by someone else. And I was told in the beginning that Peter had written a screenplay of the book back in the '80s. Over the years I kept basically downloading the book into screenplay form and rearranging things and showing it to people and a couple of years later near the end of that process I showed it to Alex [Metcalf] and we wrote a draft together. And as I tried to get the rights again, I though what would have Peter Dexter added to the screenplay that isn't in the book? So I realized all I need was the book, so I didn't really look at his screenplay.

ESQ: Was directing episodes of Mad Men over the years kind of your master plan in preparing to direct God's Pocket?

JS: Pretty much. It wasn't that fully formed when I asked to direct episodes, but I had that script and it didn't take long to realize that this is a good place to learn and maybe take a shot at this down the line. It's a pretty amazing place to direct. But God's Pocket was on the back burner, it was 95 percent finished and I started directing [episodes] because I always had an idea that I wanted to do it. So subconsciously I knew I wanted to direct it but I had never directed so it was less of a pressing reality, and once I started directing [Mad Men] it seemed like the natural next step.

ESQ: How did you get Philip Seymour Hoffman involved?

JS: It wasn't so much selling him to do it as it was scheduling. An actor that busy and that much in demand has all kinds of projects happening at the same time and so he read it and I heard from his agent that he liked it and then I heard shortly after that he wanted to play the role of Mickey, and I had actually offered him a different part. But that didn't take long for me to refigure in my head and then it became setting up a meeting and we would set them up and then reschedule them because neither of us were ever in town. When we finally did sit down I was surprised and gratified that his interest was as detailed as it was. He was talking about scenes and going in I thought he was just going to let me down easy and say, "I really like this, but I'm just too busy to do it," but then it became, "When can we find a window to do it?" Once we had Phil then everything else came together — you'd be amazed how fast people pick up your telephone.

ESQ: I went back and watched interviews that Phil did at Sundance for the film and one that stood out was him saying he came on the film because he could see how passionate you were and he marveled in seeing you evolve in front of his eyes as a director. How does that make you feel hearing someone you care for say that?

JS: You know [choking up], without getting too personal about it, you end up — after all these circumstances — you end up feeling you were just graced with a presence. I was lucky, I just felt lucky that he chose this script. I've heard other people say that and that's what it is, it comes down to: People move through the world and you watch them and admire them and then all of a sudden you end up in the same orbit and you can't believe your good fortune. So that's how I feel about it. I feel lucky that I got the opportunity.

ESQ: John, to end things I wanted to lighten the mood. On the site we made GIFs of Mad Men's greatest madcap moments. Out of these three, which for you is Roger's madcappiest moment? Roger throwing up after walking 28 floors with a belly full of oysters and martinis, Roger singing to his wife in blackface, or Roger being hit in the dick by a little person?

JS: [Laughs] Well it's hard to beat the throwing-up situation. And in fact, I think that was the first-ever GIF that I had ever seen. Someone sent that to me. But what I think you guys should do is cut the two together so that Danny Strong punches me in the balls and then I throw up all those oysters. I think that would be the perfect combination.

As Slattery requested, we have spliced together the madcappiest Roger Sterling moments into one hell of a Mad Men GIF:

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