Matthew Weiner on ‘Mad Men’s’ Season Finale, Don Draper’s Future and Bob Benson Conspiracy Theories (Q&A)

[Warning: Spoilers ahead if you haven’t seen the season six finale of Mad Men, which aired Sunday night on AMC.]

With Mad Men’s penultimate season now over, the show’s creator and showrunner, Matthew Weiner, talks with The Hollywood Reporter about its “hopeful” ending, his surprise at the conspiracy theories around Bob Benson and the random way Megan Draper ended up being linked to Sharon Tate — and what it doesn’t portend for the show’s final season (which he hasn’t yet written).

The Hollywood Reporter: Season six opened with Don reading Dante’s Inferno and then concludes with him standing in front of the hell he had grown up in. What was the arc of Don’s character in this season meant to be?

Matthew Weiner: I’ve reached the point where I realize I can’t control what the audience experiences even though, theoretically, that’s my job. People extrapolate, and I don’t have a problem with it either — it’s kind of an amazing experience as a writer to see what people bring to it — but what it was supposed to be was twofold: I really took my cue partially from the year, saying it’s 1968, and everything that we’ve introduced in the series so far in American culture, whether it was the word “Vietnam” in season two or you know, there’s a revolution going on in the world, not just in the United States.

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And I think there was some sensation that Don was going to be left behind, some guy in a suit, and be out-of-touch and be like un-groovy or whatever, and that’s not really what it was about as far as I could tell. What it was about was an opportunity for change and then, you know, as you can see from the ending, a failure at least on the culture’s part to change … [with] Nixon back in the White House and every single student and other revolution violently clamped down on. So taking that — and it’s not a history lesson — but taking that and wondering where Don was after his sort of agreement to support his modern wife at the end of last season and kind of giving up on his fantasy of romance, here he is back doing what he has always done.

And that premiere episode to me could have happened right before the premiere of the entire show. You know he could have been with Midge and married to Betty and there it is, and here he is doing it again.

So I felt this season was a descent into Don’s anxiety about why he was still the way he was, and I wanted to have a moment of realization of whether he can change or not. That he was going to have to, on some level, confront who he is, and that is the big tension in his life. People ask me if I’ve been saving stuff for the end of the show and, as you can see, no. You know what I mean? I’m not saving things for the end of the show; we really felt like that’s where it should go and so [you see] his impulsive behavior about not being able to deal with the Jaguar guy, firing their biggest client, forcing them into this merger and then attacking the guy that he merged with because he can’t have it on his own terms, becoming obsessed with this mistress who is trying to keep things lighter than they are. I always felt like it’s almost her rejection of him that makes him really fall in love with her. And so he really has all of these issues, and at the same time, we’re going to find out more and more about who he is, and it was all working up to what I came in with the beginning of the season, which was a moment of Don telling the truth, first at work in the most inappropriate place, in the middle of a pitch, and then to his children, especially to Sally. Him getting caught by Megan was not really interesting to me and probably avoidable on some level, but him being seen by Sally, that was the worst possible thing that ever happened to him. So that was the thing I felt would drive him to really say, ‘This is who I am.’

You know, we did a lot during the season — you could see it now looking back on it — we did a lot about the children. Because that’s my feeling. Ted says it in the finale, when the world is like that, you have to turn inward; you have to turn toward the things you can control.

THR: Losing Sally, whatever tenuous relation that he has with her, losing it because of the discovery of his affair with Sylvia, I think it’s incredibly shocking and damaging to him.

Weiner: I think that was a big part of it. Yeah, you saw he was in a drinking spiral after it, and I think there’s a moment in the finale, the phone call with Betty [when] Betty tells him Sally is now using a fake name and drinking alcohol, and all the things — her flaws, her crimes sound a lot like something Don Draper might have done, and Betty says, ‘Well she’s from a broken home.’ Betty blames it on herself, and you see this moment of shame on Don’s face because he knows what it’s from; he knows that it’s more than that, and you know, Sally doesn’t know who he is, but she really knows who he is because she saw that. He’s kept that secret from everybody, but that’s the idea — the shame of who he is and where he’s from is really part of the problem of why that man does what he does, and I wonder, on some level, if the audience really wants to know why he does what he does.

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That was my big anxiety, but I feel like 80 episodes into it, 78 episodes into it, not that that explains everything, but that childhood, when I started the show and was researching it and thinking about this character and the men who were like this and the men who were there, that childhood is something that they all have in common — that or it may not be as Dickensian as that, but it’s pretty bad. And in their biographies of the great men of the 20th century, they don’t talk about that, these childhoods, because it’s filled with rural poverty and broken families and runaway dads and child abuse and, you know, the sex trade, all of it.

THR: For you, does the season end on a hopeful note?

Weiner: I hope so. No, I don’t want it to be ambiguous. There are a couple of things said in that episode. First of all, I think he makes a sacrifice for Ted so he can move to California. I think that’s hopeful — or I think …

THR: Except is Megan going but Don’s not?      

Weiner: It looks like that. I think he’s in love with Megan. I think that that scene in the finale, which is really a re-proposal, when he says — and this is pretty significant language, it may pass by quickly, but it was meant as something significant — when he says it got out of control, he’s talking about his drinking, and then when he says ‘I got out of control,’ that is a huge step for someone like him. So for me, when he says that, he’s sending Ted, and I think he thinks he can manage it with his wife, but he knows it’s the right thing to do and it’s said a few times in the last few episodes about Ted being a good man, and what does that say about Don? There’s a lot in the season about doubling — about them being diametrically opposed, about them being somehow two sides of the same person or twins in some way, and it’s not like Ted is the most virtuous person that ever lived, but we see immediately that when he gets back into bed with his wife, it’s not the scene we’ve seen with Don getting back into bed with his wife, where he’s just like, like he did in the premiere, where he just gets into bed and goes to sleep.

THR: I was sort of with Don in thinking Ted’s not that virtuous.

Weiner: You know, he is in advertising! I shouldn’t have brought up the conversation because I really don’t look at these things as virtue and not virtue. I try not to judge the characters. I look at it as identifiable and accurate human behavior, good or bad. Look at Pete’s journey this season. Trudy says to him, ‘Well, now you’re alone, you have all the stuff, you’re free of everyone, you have a fresh start,’ and we find out he’s going to California in that scene, that he’s going out there with Ted. And then he says, ‘That’s not the way I wanted it,’ and she quite sternly says, ‘Well now you know that.’ Talk about a journey, right?

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I do want it to feel hopeful because, you know, Peggy has no choices — that was her story. She was forced into a new agency, she was forced to buy an apartment she didn’t want, she was sort of forced into this relationship, not forced into a relationship with Ted but then has no choice in that relationship with Ted. I’m never saying that people do not bear responsibilities for their actions, but she in particular really had no choices this season, and Pete, you know, screwed the pooch and really, really messed up his life.

THR: He did. There is always that desperation to him …

Weiner: I know, but he was so on top of the world right before they merged and then just watched himself knock his way down to being in charge of new business, which is the worst job ever, apparently.

THR: Going back to what you just said about Peggy not having choices. There is that moment where she says to Ted, ‘How nice for you that you have a decision that you can make.’ I think that was a really significant line because as you say, she has pushed against all of these forces to get to a certain point and to realize her life, and yet still she is at the mercies of these men. Is that a comment on feminism at that point? What do you hope for her?

Weiner: I don’t know, I never really look at it that way. I always just look at Peggy, about how talented she is and how hard she works. She’s relatively new at her career and she really is skyrocketing in terms of responsibility, and if you go back and watch the pilot, in eight years, where she is, and it gets extra points for the fact that she’s a woman. Mary Wells was already running an agency, but she’s not Mary Wells; she’s a very different person. They have totally different qualities, but Mary Wells is the exception; Mary Wells is the Jackie Robinson of advertising, so it’s hard to compare.

I look at it and say part of this is her own problem, part of this is the fact that she works so hard and yes, part of this is I think women don’t have as many choices, especially a young single person who is working that hard. She has her vulnerabilities, which is, you know, Abe says they’re gonna have a family, she’s already settled for not having a ring; Abe says they’re gonna have a family and she ends up in that place. And then she has just bought an apartment when Don says they’re merging. Nobody asks her, Don doesn’t ask anybody else either, so it’s not like it’s completely like she should be involved in it at all. But there she is, stuck between the two of them, and Don makes it about her, and as you see in episode 12, the one that aired last week, he is very, very proprietary to her — he does not want her to be happy, or certainly to be with a man he declared to be his enemy.

THR: He was also forced to step in and try and save that St. Joe’s aspirin account after Ted allows it to go wildly over budget without telling the client — all because he’s in love with Peggy.

Weiner: I know it may look like that, but Don is really helping them to death. I mean [St. Joseph’s] might have had a problem with it. Ted might have been able to [fix] it, but Don tattled on them on purpose and then put them in a position where he could humiliate Ted. Yes, they were being reckless and having fun and laughing and the secretary noticed it, but the minute Don sees — remember, Don has given Ted his word that he will not pursue Sunkist and that they will work as a team and he tells Harry that, and then the minute he sees Peggy and Ted in the movie theater [at Rosemary’s Baby] he calls Harry up and says go forward with that. And then the next thing he does is stick his nose in their business and find a way to humiliate them. But it all looks like help. It’s pretty evil, pretty malicious. He doesn’t want anybody to be happy.

THR: Let’s talk about one of the other intriguing relationships, which is between Pete Campbell and the mysterious Bob Benson. You mentioned that you can’t control how the audience necessarily reacts to a plot development or a new character — it must be like inserting a virus into a computer ecosystem and watching the unexpected consequences.

Weiner: I did not know that Bob would stimulate so much conversation! James [Wolk] is an amazing actor, and there was definitely a mystery to Bob [throughout the season], and I understand the imaginations going nuts with that because that is about the expectation of what the show does, and that makes me really happy.

THR: Did you read the speculation and deconstruction of his character each week and think that it was hilarious, intriguing, infuriating?

Weiner: I don’t read it. I don’t read stuff — I don’t have the stomach for it. I just sort of present my thing. But it did come back to me through my brother, believe it or not, who was the first person who told me about it. And then I started getting asked [about Bob] by reporters and people in public, so I did hear the conversation, and the actors were telling me about it too. They were asking me all season too, ‘What’s going on with him, who’s Bob Benson, what’s the deal?’ When Pete said, ‘I’ve seen something [like this] before,’ and Pete learned something, how amazing is that? Of all the people in the show, Pete learned — and it didn’t last long enough, unfortunately — but Pete realized that he should not mess with Bob, that if Bob was this kind of person who had gotten this far, he should not mess with him.

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THR: That’s interesting because I also thought Pete entertained the ideas of using Bob in some kind of nefarious way, and that’s why he didn’t rat him out as he tried to do to Don early in the show.

Weiner: I’m sure, I’m sure he had fantasies of lots of things about Bob, but we loved the idea that it showed how much Pete had that Bob was fixated on him, and it showed how Pete is not a good manager until that moment when he decided to not out him or go head-to-head with him. Bob as a character fits in to me the same way Don does: We all know we work with people like this all the time and this is one of the only places in the world where you can succeed. And it’s almost a testament to the meritocracy principle because if you’re doing your job what is there to say? But I’m not even sure if Bob is gay — he might be one of these polyamorous people who is fixated on Pete. That’s what I like about him.

THR: That is exactly what I wondered. Is Bob actually gay? But I put a darker spin on it. I saw him potentially as a type of grifter who preys upon people and does what it takes to seduce and betray or seduce and conquer them.

Weiner: There is that. That is definitely true that he has a lot of that. There’s also the other quality that people who are like that have. They are convincing because they really do believe it, and that’s why it’s so dangerous sometimes to spur them, because then they — the rejection can also be something that is insurmountable. So is he so Machiavellian that he can just turn it off and on and he’s faking all of it? It’s pretty convincing when he tells Pete that he lives and dies for Pete’s happiness. I think you’re talking to someone who is not faking it. And he certainly doesn’t want to be called a degenerate.

THR: When he says you should watch —

Weiner: Yes, you should watch what you say to people and everyone heard. He seems pretty formidable at that moment. When he says, ‘You got it,’ in the finale. When Pete says, ‘Why don’t you write that smile off your face,’ and he says, ‘You got it.’ It’s pretty scary.

THR: It was chilling. And then it leads to one of the great humiliations of the series: what he does to him at GM …

Weiner: Yeah, it’s nice to sort of pay stuff like that off; we all know that Pete can’t drive.

THR: I know, I felt sorry for him!

Weiner: I know, but he shouldn’t have messed with Bob. Pete threatened him.

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THR: Is Manolo, the nurse, Bob’s lover or just his friend?

Weiner:  I think he’s his friend. He may know him through the, what would then be the underworld of gay life, but he’s definitely his friend. I mean he definitely knew him. I don’t know if he was his lover or what their relationship is, but Manolo has an alias and it’s … I started off the season with that too. The idea that they hired this nurse — it actually came up in the writers’ room that Bob would be the way that Pete got the nurse. That was not something I came in with, but the nurse was there [when he conceived the arc of the season] and thought that Dorothy [Pete’s mom] was rich and he was clearly gay, and yet at the same time probably her lover and was going to kill her, and Pete and his brother would have to decide they didn’t want to financially follow up on it.

THR: But he did kill her?

Weiner: It sure looks like that.

Honestly, a lot of it was about the generations passing. Starting with Roger’s mother, it was the idea that the world was really changing, that whole generation was gonna be disappearing. Those people’s parents and obviously Pete’s mother had other problems, and certainly his relationship with her was not as warm as Roger’s, but we felt that in the end, he wasn’t going to pay to clear her name.

THR: I did like her moments of lucidity: ‘You were a sour little boy and now you’re a sour little man.’

Weiner: Yeah, isn’t that incredible? It’s brutal but, well, you know, she did raise him.

THR: It’s sad we won’t see her again.

Weiner: Well, there’s always the dream life.

THR: One of the other obsessions of the audience, or at least a portion of the audience and the Internet, was the relationship between the character of Megan and Sharon Tate, which is a fascinating thing.

Weiner: My brother told me about that too, by the way. Then I heard from my costume designer, Janie Bryant.

THR: She was quoted about the T-shirt and that it was a deliberate decision to use the same T-shirt Sharon Tate wore in a famous photo before she was murdered. How did that arise?

Weiner: It was kind of a funny thing. The T-shirt arose like everything clothing related arises on the show: I write something in or Janie has an idea and then we try and substantiate it. And believe it or not, [having a] woman in a T-shirt was something I’ve been trying to do on the show but have not found a lot of evidence for before this year. We wanted Megan in a Disneyland T-shirt in season four in the finale when Don proposed to her, and it basically became clear that there aren’t a lot of women’s T-shirts worn during this period.

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For Janie, it really just became a matter of, ‘Here’s some substantiation of a T-shirt, this is what it looks like. It doesn’t have an ironic saying, it has this Viet Cong star on it, and Sharon Tate’s wearing it. Here’s the picture of her.’ And I say, ‘Great. I want that exact T-shirt.’ But it was not foreshadowing anything! I didn’t think of it. I wish I could say I did. Not at all. Sharon Tate, she’s in Playboy, that picture. I was like, ‘Yeah, great, a sexy T-shirt.’ Half the pictures we look at of models and sex symbols — the people are dead, so I don’t even think about it.

THR: Nobody died this season, at least none of the main characters died, and there was a lot of speculation that someone would.

Weiner: I know, I know, I guess because we did it last year. That’s not really an arrow people should think is in the quiver. I don’t mind that the audience is speculating about it. But the Lane [suicide] thing was a very specific thing. It’s one of the ways we keep things fresh, not to repeat storylines, and that’s a very particular storyline.

THR: Although with Don, the amount that he drinks, the amount that he smokes, how long can he live?

Weiner: His father died really young, getting kicked by a horse, which was also alcohol-related. I don’t know. You’ll have to watch. I can’t imagine that in 2013 he would be around or even 1999. He’s not gonna end up teaching a course at The New School in advertising. But these guys, it depends on your genes. He definitely lives really hard, but it’s part of his issue. For a man who is so afraid of death and has it looming over every aspect of his life, he really is incredibly self-destructive. I don’t mind that as a tension, believe me.

THR: When do you start writing the final season?

Weiner: I will go back in July to begin my rumination process, and then we will start shooting in the late fall.

THR: So can you give us any sense of how Don resolves the eternal question of dealing with who you really are, not who you want to appear to be?

Weiner: I can’t! I don’t really know what I’m going to do, and I don’t know that the show will ever offer anything [concrete]. I find it difficult to even express resolution on the show. It’s not a creative problem for me. People asked last year why we showed Lane’s body, when he [hanged] himself, and my basic feeling was, in the end — I mean, of course it was the story, and I wanted the impact to hit and I wanted us to know how the characters were dealing with it, but I also knew if I didn’t show his body, people would not really believe he was dead.

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Resolution in itself is a mystery in this world. I don’t know what to say. Other than death, and even in death, I don’t know that there is that much resolution in [real] life ever anyway, and I’m always trying to approximate that on the show. But in terms of the last season, without being coy at all, I haven’t really thought about it. I have something that I think is the image for the very, very end of the series. Other than that, I just sort of leave things where they are. I think you can feel all of the basic tensions of the series, of the premise of the series, are still intact. I haven’t protected them in any way. The people have evolved; we know more about them than ever, and I just want to be able to leave people with some sense of satisfaction that they were glad that they were on this journey for all these years.

she seems to have green lit or not green lit my friends’ things, so to me she’s a very powerful, mysterious person.” 

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