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 …”