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Frank Ockenfels 3/AMC

In the first episode of the first season of Mad Men, Don Draper is convinced that he is, in the parlance of the times, a big fat zero: “I’m over,” he laments, “and they’re finally going to know it.” It is March, 1960, and the creative genius of the Sterling Cooper advertising agency cannot imagine a new way to sell the pleasurable death sticks that have kept his company afloat for years. Until he does. Lucky Strike tobacco, he thinks, in a pure spasm of inspiration: It’s toasted.

Now it’s Don who is toasted. Six seasons later – nine years in the show’s chronology – he has finally run out of road. When we last saw Don, magnificently played by Jon Hamm, he was stripped bare: loathed by his oldest child; a stranger to his other children; pitied by his ex-wife; abandoned by his current wife; his friends – well, Don never had friends. He only ever had his bottle, and his secrets, and his job. By the end of Season 6, even that had disappeared, as his fellow partners gave him the boot, furious not at Don’s boozing or womanizing – there would be no one to turn on the lights at the office if they got rid of the boozers and womanizers – but at the fact that he seemed no longer to believe in advertising. That was the one transgression they couldn’t forgive.

Frank Ockenfels 3/AMC

That’s right: At the end of last season, in arguably the show’s finest moment, Don began to change. A pitch meeting for Hershey’s chocolate bars went disastrously wrong when he decided that he could no longer sell the nostalgic lie that advertising loves; he told the stunned Hershey’s executives that he was rewarded with a chocolate bar by the whores who raised him. At that moment, Don Draper’s greatest advertising project – himself – came unwrapped. Is being naked the beginning of truth? Is this Don’s first step, long overdue? And, if it is, is Mad Men itself toasted? Will Don keep us watching now that he may be on the road to recovery?

The greatest show in television’s history (I will fight you on this) begins its last season on April 13. Or at least half of it begins: Its 14 episodes will be split in two, with seven episodes airing this spring, and seven next. The show’s creator and main writer, Matthew Weiner, has said he has had the final image in his head for a long time. Could it be Don dead? In a pit of flames? (Don’s been reading Dante’s Inferno, a gift from another ill-chosen girlfriend.) Where will Don’s journey take him?

Nowhere, most likely. One of the greatest things about Mad Men is its stubborn rejection of the journey of self-improvement. John Slattery, who plays charming rake Roger Sterling, described Mad Men’s characters this way: “They continue to make the same mistakes, only in slightly different form.” Or as Weiner said recently, “We repeat things in life all the time.”

Frank Ockenfels 3/AMC

For a show that is fixated on transport – key scenes take place in cars, trains, planes and airports – it’s remarkable how little ground the characters actually cover, in terms of emotional progress. Don, in particular, has been resistant, pinned in place by the secret he carries. (He has stolen the identity of a dead man; every day is a lie.)

Look at the promotional stills for Season 7, which are set in an airport. All the characters are dressed in late 1960s psychedelia: Don’s wife, Megan; his daughter, Sally; his co-workers Stan and Harry. Even Roger’s wearing Chelsea boots. Everyone’s embracing grooviness with open arms.

But Don? Don is dressed almost exactly as he was in the series premiere, in a conservative boxy suit, fedora in hand. His hair is still parted with a razor. He’s like a chameleon who’s found safe camouflage, and is terrified to change colours in case he’s discovered and trapped. But now, just maybe, he’s free of that.

There is one movement the characters can’t avoid: They are propelled into the future, whether they like it or not. The last season ended around Thanksgiving, 1968, with Don finally admitting to his children that his fairy tale was only a cover, by bringing them to the cat house where he was raised. The disruptions of 1968, the riots and assassinations and protests, were explicitly manifest in Don’s downward spiral. (How bad did it get? Well, you probably don’t want your pubescent daughter catching you offering pants-free comfort to a neighbour’s wife.) As Weiner has said, “Don was going to be out of control because the culture was out of control.”

Stephen Hughes and Rachel Idzerda for The Globe and Mail

Unless Weiner is being a very cheeky monkey, the new season will begin in 1969, and the series will span one of the most tumultuous decades in modern American history. A decade that dawned with John F. Kennedy’s election has now faded out with the triumph of his former rival, Richard Nixon. Don, a pragmatist as all survivors are, has no patience with idealism, unless it will help him sell a product. “I’m doing just fine,” he said in last season’s finale. “Nixon is president, everything is back just the way Jesus wants it to be.”

There’s one lie in those sentences, and possibly two, but Don, in the manner of many great fictional characters, is an exceptional truth-teller except when it comes to himself. According to Weiner, the historical record won’t intrude as heavily this season, but there will have to be some reckoning with 1969, the year America came to terms with stories it told itself (precisely as Don is having to reconcile with his own tattered myth). It was the year of the moon landing and the inaugural flight of the 747, but also the year of the Manson murders, the Zodiac killer and Altamont. The story of the My Lai massacre broke. The Stonewall riots provided dawning recognition that people like Sterling Cooper’s tragic art director Salvatore Romano would no longer lie down and take a kicking.

So where will Don be in 1969? He has always been confounded by the future; he listened to the Beatles’ trippy Tomorrow Never Knows and walked away in exasperation. But one of the Season 7 promotional videos provides a clue. It shows an animated Don, in all his boxy-suited glory, walking through a psychedelic doorway to the sounds of David Bowie’s The Man Who Sold the World, released in 1970. Now that Don realizes he was the man who sold the world – and now that he seems to be leaving that business behind – is there anything left for Mad Men to sell? Unless it’s the message, bleak but true to the show’s vision, that when Don takes one step forward, he inevitably takes two back.