Poor Bert. I should’ve known it was near the end. Every time an old man starts talking about Napoleon, you know they’re going to die.

While the passing of Bertram Cooper, co-founder of the ad firm SC&P, was a big highlight of Mad Men’s midseason finale, the episode’s biggest star was none other than Roger Sterling, played with endless panache by John Slattery. The last episode of the AMC series ’til 2015, titled “Waterloo,” saw the freewheeling Sterling surprise the firm by orchestrating a stealthy coup against the scheming Cutler and his beloved IBM computer by striking an eleventh-hour deal to sell off majority ownership in the firm to an exec at McCann Erickson, thus securing his—and his partner in crime Don Draper’s—future.

“I think you should buy the whole company because I have a vision: all our accounts, our cutting-edge computer, and the employees I know to be worthy as an independent subsidiary of McCann,” says Roger.

And Slattery has been a very busy man of late. In addition to playing the dapper ad man on television, he’s also managed to squeeze in his feature directorial debut, God’s Pocket. Based on a novel of the same name by Pete Dexter, the film centers on the residents of the titular gritty South Philly neighborhood whose lives are thrown into further turmoil following the death of troubled teen Leon Scarpato (Caleb Landry Jones), the son of Jeannie (Christina Hendricks) and stepson to Mickey (Philip Seymour Hoffman).

The Daily Beast spoke at length with Slattery about Mad Men’s midseason finale, the state of Roger Sterling, and working with the late, great Philip Seymour Hoffman.

The midseason finale of Mad Men was excellent. I wanted to discuss the last scene, and the decision to send off Bert Cooper (Robert Morse) with a song-and-dance. What do you think the rationale was behind that?

Matt’s [Weiner] always been a fan of Robert and obviously knew about his musical background, but I don’t know why he chose that particular moment. There’s a point at which the character’s expressed, “I’ve seen enough… this isn’t my world, it’s your world” sort of view. Mad Men’s always been about change, and the evolution of all these characters. I think it’s also about Don struggling—as he always has—with the value of what he does. Where’s the value in what he does, in advertising? There’s a battle between cynicism and idealism. He’s created himself wholly from the very beginning and he’s wondering what he’s created for himself. Despite all the changes, the characters on Mad Men are always trying to figure out, “Who are we?”

Mad Men is very big on surrogate parents on the show, and Roger always viewed Bert as a surrogate father figure. He was even babysat by Bert’s sister, and despite Roger’s name being on the firm, it’s his late father’s name that is there alongside Bert’s, not his own.

I think he is exactly that—a surrogate father—and a reminder to Roger of from whence he’s come; by that, he’s also a check-and-balance system to Roger’s decision-making process. Bert, like all the characters on Mad Men, had his own eccentricities and code of ethics, and they’re balanced against everybody else’s. And they make bold choices. Roger’s made many bold choices in his life—leave one marriage, start another, experiment with drugs—all in view of Bert, who’s of a different generation. Bert was always seen as an authority figure, for better and worse. People in that capacity provide wisdom, but also unwanted judgment and authority.

Do you have favorite memories of working with Robert Morse? His casting was such a nice touch to the show, and a great nod to How to Succeed in Business Without Really Trying.

He’s just a great guy. He and I come from the same hometown—Newton, Massachusetts. I’d pass his house on my way to the orthodontist. He was a legend—is. Big Boston sports fan, too. We talked about the Red Sox all the time.

Roger’s stealthy save of SC&P was cool to see because, while we did see it coming in a sense with Roger’s steam room encounter with the McCann Erickson exec, Don has also been slowly mobilizing his troops for a Cutler showdown.

What’s refreshing about episodes like this is just when you think a character is one thing, he tends to be far more competent or able than you would’ve thought given the way he acts most of the time. Roger’s a good businessman; he knows how to close a deal, and he knows a good thing when he sees it. And obviously, the company means a lot to him. Throughout the course of the show, he’s always been wary and aware of the fact that people think he’s been handed the whole thing, but he’s worked very hard at the company for over 30 years—started at the bottom and worked his way up—so he goes to Bert when he sees Cutler trying to gain control and says, “What do we do?” and Bert’s advice is to let Cutler take over. He tells Roger, “You have experience, but you’re not a leader of men.” It’s a tough thing for Roger to hear, but he goes along with it—until Bert passes away. Then, he realizes that without Bert—without those votes—Cutler would really take over, and that’s the last thing he wants to happen.

Roger does have a chip on his shoulder because people think he was handed the company, and Don not only wasn’t handed anything and created himself from whole cloth, but also has a huge chip on his shoulder because of it. Do you think that’s why these two characters have such a great affinity for one another?

Yeah. I also think Roger sees just how brilliant Don is. Roger can close a business deal, read a room, and charm a dinner table, but Don is the creative genius behind all those deals. Without a guy like Don Draper, it doesn’t matter how many deals you make if you can’t come up with the ideas. But all that is right—they are friends, and they are loyal to each other—but the bottom line is he sees what a brilliant guy Don is.

Roger’s had a tough time this season with his daughter, Margaret, who’s now living on a hippie commune.

They’re just such well-written scenes. To have your own child tell you that this is how they’re going to conduct their life based on the example you set for them is so powerful because not only are you guilty of being a bad father, but you’re also guilty of creating a bad mother. She’s saying, “Well, what do you expect me to do given the example you’ve set for me? I’m fine, I’m here, you were never there, and your secretary bought me Christmas and birthday presents. And knowing that, I know my son will be fine without me.” So Roger’s paved this whole bad example of father-and-motherhood forward for future generations.

The “man vs. machine” theme has been very interesting this season—punctuated by the Ginsberg slicing off his nipple over the IBM. That whole subplot seemed to me like a reference to the Ginsberg poem “Howl” and the idea of man rebelling against the status quo.

The Ginsberg character has always been against conformity and the bureaucratic mechanism—the “machine” that is the government, the war, all that stuff. In a lot of these scenes, you can’t figure out if it’s professional, or personal. Is it actually the IBM, or is it Peggy? And they’ve all been skeptical of the computer. Roger’s skeptical of the computer and Harry, since it’s going to make Harry Crane seem important.

Let’s talk about God’s Pocket, your feature directorial debut. What attracted you to this gritty story in South Philly? Did you see similarities between this town and the one you grew up in in Boston?

It wasn’t so much the physical similarity but the tonal similarity that I appreciated—the dark sense of humor and this concise ability to read a room, turn a phrase, and basically say what they wanted without being transparently needy. Also, the lack of self-pity was part of the ideology when I grew up. “Move forward, and get on with it.”

How did you assemble this crazy cast? Philip Seymour Hoffman, Richard Jenkins, John Turturro, Christina Hendricks, Eddie Marsan, the list goes on.

Once I figured out how to put the Pete Dexter book into screenplay form, and sent that to Phil Hoffman, he understood the script and wanted to be a part of it. Once I had those two things, it’s not surprising how fast you get your phone calls answered!

I remember that great scene you and Hoffman shared together in Charlie Wilson’s War—the epic shouting match where he broke a few windows. Was that the first time you two had met?

[Laughs] No, we’d known each other since the early ’90s. I met him through a mutual friend, and then we’d see each other around New York—lived in the same neighborhoods—and then worked together on that film. We knew each other socially a little bit, but when I sent him the script I went through the proper channels. We weren’t best friends, but we were friendly.

How many windows did he end up breaking in that scene, as far as the number of takes goes?

We only shot it like… two or three times, and they’d keep putting a new window in. Phil had an adjustable wrench that he grabbed off some guy’s wagon or something, and he broke it easily the first time, but the second time he had to hit it a couple of times before it broke. [Laughs]

God’s Pocket was really about loyalty to one’s community, and the camaraderie that this tight-knit group of lost souls has with one another.

The issue of being from a certain place, and whether you’re an “insider” or an “outsider,” was something that I found very interesting as far as the character of Mick goes, played by Phil. Mick is constantly fighting his way into a community that’s pushing back against him because he’s now “one of them,” and he starts to question why he wants to be a part of this community. A lot of places are like that—they’re very insular, and not the easiest of places to live, but they won’t let anyone insult them. They can talk trash about their own people, but no one on the outside can. There’s a lot of that in this country—tribalism, nationalism, call it what you want—where people are protective of their own. It’s silly to me, to some degree—this territoriality for its own sake. Is it better to be a part of a community against your own instincts, or be your own person and be ostracized?

There’s a crazy scene in God’s Pocket where Hoffman is trapped in a rainstorm and struggling mightily to drag a dead body into his meat truck. I’m assuming that was the actor he was dragging and not a dummy?

Yup. We had a dummy but it was never really going to look like Caleb Jones, the actor, and those two actors being who they are, they wanted to do it themselves. So, it was Phil dragging Caleb around in the rain for a few hours. And Caleb isn’t a small guy—he’s 6’2”. But you use that to your advantage. Because it was so difficult for Phil to drag Caleb around, it adds to the drama.

Was the early scene where Hoffman is having some pretty animated sex with Christina Hendricks’ character a slight tip of the hat to the opening of Before the Devil Knows You’re Dead?

No, not really. We discussed that because that movie opens in a similar way, but the book opens that way. I had in mind a sequence where Mickey is driving through the neighborhood and he sees a few scenes—kids blowing up trash cans, other little vignettes—to give you a feel of the place. But the only day it rained was that day, so those little vignettes wouldn’t cut in to the rest of the movie. So, our editor came up with the idea to put the funeral at the beginning of the film to give a sense of place where, in the middle of this “dignified” funeral, the funeral director gets punched in the nose so you get a sense that it’s OK to laugh at these people.