Had HBO’s True Detective premiered last year, the sixth season of Mad Men would have aptly proven Rust Cohle’s observation that “time is a flat circle.” Beneath the longer hairdos and shorter hemlines, the clouds of marijuana smoke and the unremitting sound of police sirens, lies a story now twice-told – of a man tortured by his past, struggling with his present, and looking at an uncertain future. But if Don Draper once was, to paraphrase Austin Powers, someone “men wanted to be and women wanted to be with,” age has only served to coarsen him, to erode his humanity and expose an ugly core.
As the season begins, we catch up with Don on a “business trip” to the Royal Hawaiian Hotel in Honolulu, leafing through Dante’s Inferno, musing on going astray and finding himself alone in a dark wood. But the reference is too cute by half. Don has been alone in that dark wood his whole life and a theme that would be repeated during the season occurs at the end of the premiere – mirroring. In the show’s very first episode, we do not discover that Don is married to Betty and carrying on an affair with Midge until the end of the episode. Now, the image is reversed – Don and Megan appear to be happily married – lazing on the beach, getting high and having sex, and enjoying a luau, but at the end of the episode we discover that Don is having an affair right under Megan’s nose with their neighbor, Sylvia Rosen.
And it is Don’s affair with Sylvia, its dissolution in an ugly role play of domination and control, and its brief resurrection and discovery by Sally that animates much of the season’s storytelling. Sylvia is another in a line of brunettes that have cycled through Don’s life, but with each succeeding liaison, their proximity to his “normal” life drew closer. Midge and Bobbi were New Yorkers and at a safe distance from Don’s home life in Ossining. Suzanne, Sally’s school teacher, was in the same town, heightening the risk of being caught, but Sylvia is one floor down in Don’s Park Avenue building, making the discovery of their tryst almost inevitable.
If the recklessness of cavorting with a neighbor was not strong enough indication of the death spiral Don is in, the pitch he makes to management of the Sheraton Royal Hawaiian, with its allusions to shedding of skin and disappearing into a watery ever after, immediately brings to their minds images of suicide. Don misses the reference entirely, but when he asks Stan if he sees it too, Stan enthusiastically says yes, noting that is what makes the ad so cool. Later, during an ill-fated trip to California and in a hashish-induced hallucination, we see Don face down in a pool, the spectral image of Private Dinkins, a man Don met in Hawaii (and now dead), observing that “death doesn’t make you whole, you should see what you look like.”
Mix in Don’s stratospheric consumption of alcohol, never-explained (but omnipresent during the back half of the season) cough (the early stages of emphysema or lung cancer?), and the unremitting shame he feels in the wake of Sally’s discovery of him in flagrante delicto result in a painful denouement – first, of a soul baring pitch to Hershey’s executives that starts as a classic Norman Rockwell-esque portrait of a simpler time when young Don is rewarded for mowing the lawn with a chocolate bar but devolves into a searing confessional of the candy being his reward for picking the pockets of johns being serviced by the women in Uncle Mac’s brothel; then, after that flame out, his involuntary separation from the firm and decision to take his children to his childhood home, now rundown and shabby.
The subtle-as-a-sledgehammer crash Don experiences in 1968 is overlaid against more mirroring to prior seasons. Like season three, season six offers flashbacks to his childhood, except now, instead of examining Don’s relationship with his father Archie, the story picks up after his death and Don’s time being raised by his step-mother Abigail and his Uncle Mac, the proprietor of a whore house in hardscrabble Pennsylvania. And in case the root of Don’s awful adult relationships with women is not obvious from learning of his deflowering by a hooker or his voyeuristic witnessing of Mac’s sexual liaison with his step-mother, it is left to Betty to drive the point home as the two are engaging in some post-coital pillow talk. There, Don luxuriates in their physical closeness (who knew he was a cuddler?) and emotional intimacy, while poo-pooing the nexus between sex and love. Betty demurs, noting that most people connect the two and that Megan’s biggest mistake was realizing the worst way to get to Don is by loving him.
Ultimately, the mirroring of season six reinforces Don’s long ago observation that people don’t change. Don is a drunk who neither values personal nor professional relationships and makes his decisions with little regard for others. Where he could once fly by the seat of his pants, or, as Pete put it, “swing from vine to vine,” narrowly escaping danger, whether it was a pitch to a client or the discovery of his checkered past, little by little, the façade has been exposed. Betty no longer lives in the dark about who Don is, Megan quickly susses out his boredom, Peggy stands up to him and calls him out for his awful behavior, and now, Sally has seen him at his lowest point. Where once he confidently sold “nostalgia” in the clothing of cherry picked images of his own life with Betty and the kids, Don cannot pull off the lie of an idyllic childhood of freshly cut grass and a trip to the corner drug store. Rash business decisions years ago that torpedoed accounts or rebooted the firm always worked out, but having merged companies in order to land General Motors, Don created a level of chaos he was unprepared for and could not deal with.
That Don is slowly losing his grasp is of a larger piece to the story being told in season six. From the omnipresent police sirens to the seismic cultural shocks that reverberated in the deaths of Martin Luther King, Jr. and Robert Kennedy, Don can’t go to the movie theater without seeing the allegory of mankind’s destruction projected on a screen and his once hip Rat Pack era look seems dated and square when he and Roger alight to California as “conquistadors” (Roger’s word) but return deflated – shopworn remnants of a time and place that have come and gone. So it is unsurprising that Don seeks order and control, but it manifests itself in disturbing ways, be it the emasculation of Ted Chaough or the humiliation of Sylvia in their hotel room tryst.
The “falling man” motif in the show’s opening credits has been interpreted by some to suggest suicide, but I always thought it meant that just as Don was about to splatter to the ground, instead of becoming an inkspot on the sidewalk, he emerged, perfectly coiffed, cigarette in hand and ready to start anew. And that has largely been true – Don has been brought low at various times only to rise again with a new lease on life; however, in an era of “difficult men,” Don’s fall is consistent with the likes of Tony Soprano and Walter White, two other “anti-heroes” whose larger than life personas encouraged viewer loyalty and devotion before reminding us that these were not good people. Indeed, if Tony’s fate is either to live his life constantly looking over his shoulder or having met an untimely demise in Holsten’s diner, and Walter lost everything in pursuit of caring for his family, one can only expect that Don’s fate is similarly bleak. Actions in a moral universe must have consequences, and no matter his protestations, the blizzard of apologies he has uttered for his indiscretions great and small, or the seductive vulnerability he has wielded when it suited his needs, if you live your life like there is no tomorrow, one day the bill comes due.
 The Secret Fate of Life, True Detective, Season 1, Episode 5.
 The Doorway Part I, Season 6, Episode 1.
 Smoke Gets In Your Eyes, Season 1, Episode 1.
 Don’s paramours are all brunettes.
 A lesson Pete Campbell learned when he bedded one of his Cos Cob neighbors. To Have and To Hold, Season 6, Episode 4.
 The Doorway Part II, Season 6, Episode 2.
 A Tale of Two Cities, Season 6, Episode 10.
 In Care Of, Season 6, Episode 13.
 See, e.g., Out of Town, Season 3, Episode 1, Seven Twenty-Three, Season 3, Episode 7, Shut The Door. Have A Seat. Season 3, Episode 13.
 Don refers to having been raised in coal country, “Illinois, by way of Pennsylvania” to Conrad Hilton. My Old Kentucky Home, Season 3, Episode 3.
 In Care Of, Season 6, Episode 13.
 The Collaborators, Season 6, Episode 3.
 The couple’s one-off liaison while visiting Bobby at sleep away camp offers one of the season’s few grace notes; but even then, it’s tinged with melancholy. The Better Half, Season 6, Episode 9.
 The Mountain King, Season 2, Episode 12.
 The Wheel, Season 1, Episode 13.
 Bobby’s reaction to the ending of Planet of the Apes is one of the season’s great lines. The Flood, Season 6, Episode 5.
 A Tale Of Two Cities, Season 6, Episode 10.
 Man With A Plan, Season 6, Episode 7.
 Difficult Men, Behind the Scenes of a Creative Revolution From The Sopranos and The Wire to Mad Men and Breaking Bad, Brett Martin.
 Smoke Gets In Your Eyes, supra.