In different phases of his work on Mad Men, the show’s creator, Matthew Weiner, has said he has come to identify with one or another of his characters. Now, as the final season nears its premiere, his heart is with Roger Sterling, the naughty ad man who gets all the best lines. Weiner is not a hound dog like Sterling (he is married to the mother of his four children). Unlike Sterling, he does not experiment with psychedelic drugs (“I don’t have the constitution for it,” he told me). He doesn’t look much like Sterling (Weiner is younger and shorter, and prefers L.A. casual to Madison Avenue dashing). And they aren’t temperamentally all that similar (Sterling is wry and aloof, Weiner focused and excitable). But they both have “very intense dreams,” Weiner says, that deeply color their everyday perceptions. And both are “interested in certain adventures,” which in Sterling’s case might mean an LSD trip or kinky sex in the office, and in Weiner’s means pushing the show’s central character, Don Draper, off a cliff and showing us how he lands.
When the first episode of Mad Men aired, in July 2007, Weiner’s hope was to have the show renewed for enough seasons to cover the entire decade of the ’60s. Since then, we’ve followed the characters from the suburban ennui of the early part of the decade through the turmoil of 1968, a span that includes the introduction of free love, Hare Krishna devotees, wide lapels, and the assassination of Martin Luther King Jr. By now, Weiner has lived with these particular characters long enough to have the “meta-experience, if you go back and watch the first season, of nostalgia.”
Season Six ended on a note that hinted at possible redemption for Draper. After alienating his wife, his mistress, and his daughter, Sally, and losing his job, Draper takes his three children to the Amityville Horror–style house that was his childhood home. In an earlier episode, Sally had complained that she didn’t know anything about him. (The audience knows that he was raised in a whorehouse and his name isn’t really Don Draper, but his kids don’t.) She looks up at that house, and then looks knowingly over at her father—a look that Weiner said he hoped the audience would realize was “mammoth,” a look suggesting that after all these years, Don Draper might finally stop running.
“I can’t really” describe the final season “without spoiling it,” Weiner told me, and besides, he’d shot only five of the final 14 episodes when we spoke this winter. But he did say that it will be about the consequences of past behavior. “Can you undo something bad that you’ve done? Is that possible?”
A hint of redemption is different from a promise, however. And Weiner can be dismissive of what he calls the “Hollywood reaffirmation thing.” In the end, even Walter White, the controlling, deeply immoral hero of Breaking Bad, “made himself not a bad guy by killing all the really bad guys and providing for his family,” Weiner told me. In Mad Men, by contrast, the leads are flawed in the way of Old Testament characters. Their suffering can seem randomly distributed, and the outcomes of their stories are rarely tidy or satisfying. “The good guys don’t always win,” he says. And “if you spend a few hours in the shoes of the bad person, you might do the same thing. You’re doing bad things. You don’t know why. Don feels the same way.”
Whatever happens to Draper will take place against the backdrop of an era Weiner clearly sees as disappointing, in which hopes are deflated, various hypocrisies are laid bare, and cynicism eventually reasserts itself. “The chickens are coming home to roost,” he says. “The revolution happens, and is defeated,” in 1968. “There is cultural change, but the tanks roll into Prague, the students go back to school.” All of that leads to the era Weiner witnessed as the child of a liberal father in the 1980s, by which time the activists of the ’60s had flipped and become the “greediest—can I say motherfuckers in The Atlantic?” When he talks about individual characters, Weiner is a gentle creator, reserving judgment about their sins. But when he talks about society at large, he is a god of vengeance, and doesn’t hesitate to condemn. “I was 18 years old, watching the world being run by a bunch of hypocrites, is what it was. And at the same time, they were telling us how they had invented sex, how great it was to do all those drugs, they had no responsibilities, they really believed in stuff, they were super-individuals. Then along comes this incredibly repressive, selfish, racist, money-grubbing …”
Weiner is the slightest bit touchy about his reputation as a control freak, especially when it comes to the period details of the show. (He told me that anyone who thinks any form of entertainment—a live football game, Project Runway, improv—“does not have the level of control exerted on it that I have is mistaken.”) Still, in the run-down, unglamorous warren of AMC’s studio offices, his is an island of neatness and order. The bar in the corner once graced the office of Roger Sterling, and the walls are decorated with vintage ads and a Japanese poster for Mad Men.
I had expected Weiner’s mind to be precise and intensely rational, and it was—but those strains coexisted with others. The first thing he mentioned when we sat down was having peeked into an office earlier that day and seen someone, from the back, talking. Weiner said he was suddenly consumed by the fear that the man he saw was talking to no one. Much of Mad Men is driven by Weiner’s id, by his own dreams, by what he calls a “wordless instinct,” a conviction that “truth is stranger than fiction.” Some aspects of the show may seem “dreamlike or whatever” to others, but Weiner told me he often experiences things in a very different way than most other people do.
Several times during the course of our two-hour conversation, I realized that some things about Mad Men that I thought everyone agreed upon were not obvious to its creator. “Did you know Glen was going to become cool?,” I asked. “That was such a surprise to me.” Glen is an old friend of Sally Draper’s, and he shows up in Season Six as an alpha at a boarding-school party, liquor in his pocket. Until then, he’d been a neighbor’s weird son who’d spied on Betty Draper, Sally’s mother, on the toilet, then asked for a lock of her hair. Although he is played by Weiner’s actual son, I asked the question anyway, because everyone knows that Glen is a little weird (creepy is a word often used to describe him). Well, everyone but the man who created him. “I never thought Glen was weird,” Weiner said, looking not injured, just genuinely confused. “I identify with him a lot, not just because he’s my kid. I mean that character, a lot of the things that he did.”
Weiner is not an actor, but sometimes he goes to casinos and pretends to be Tunisian, Russian, or Armenian. I’d heard him confess this on a podcast once, so I asked him about it. (This also seems like something Glen might do one day.) Why would he pretend to be someone else? And why those nationalities? He doesn’t do it to take a holiday from his persona, he told me; although his name is famous, people generally don’t recognize him. He does it just to do it. Perhaps a clue to his motivations can be gleaned from a line that had lately been echoing in Weiner’s head, a line that had been written for Bert Cooper, one of the founders of the show’s original ad firm: “When you hit 40, you realize that you’ve met or seen every kind of person there is.” Weiner is in his 40s, and is suddenly “realizing I am running into the same kind of people.” He doesn’t know what he wants to do after Mad Men, and he doesn’t seem to want to think about it. Roger Sterling sometimes talks this way too, about life as a series of doors that lead only to other doors. He talks this way when he’s on the psychiatrist’s couch and is inching toward depression, when work and women are not exciting enough to hold his attention. But then he has a vivid dream or one of his wacky adventures—going to a casino?—and color is restored.
“I have a very normal life,” Weiner says. “But I don’t, obviously. I have this entire toolbox to live my fantasies, and that has been a far less destructive way to live them … And I think that makes me a very lucky person.”