"Midway in our life's journey, I went astray from the straight road and woke to find myself alone in a dark wood." - Dante Alighieri "The Inferno"
The sixth season of Mad Men began with all the subtlety of a kick to the head. Death, lingering and in shadow until Lane Pryce committed suicide, is now front and center. Don Draper, who did not so much find himself alone in that dark wood midway through his life's journey as having lived most of his life in it, is consumed with his mortality. On the other hand, Roger Sterling, who never wanted for a single thing in life, has been parachuted into that same foreboding place grasping for answers.
Much of the season premiere presents Don and Roger as counterpoints in search of deeper meaning. The last time we heard Don in voice over, he was collecting the last of his belongings from his former marital home in Ossining, wizened and world weary over the life lessons he had learned.  Now, eight months removed from Lane's death, Don is immersed in an interior world far grimmer than infidelity or trouble with drink. No, Don has gone from doodling nooses and equating a Saturday night in the suburbs to blowing his brains out to externalizing his emotional baggage through red flags that are as big and bright as day.
That Don would struggle with mortality is unsurprising. His own birth resulted in his mother's death and he was tarred with the label of "whore child" during his hardscrabble roots. His father, a "dishonorable man" , was killed in a freak accident in front of him , and a young Dick Whitman reached for a new life when an accidental explosion in Korea killed Lt. Don Draper.  The death of Anna Draper consumed Don - a loss of "the only person who truly" knew him  and he felt responsible for Lane's suicide, having fired Lane for embezzling money from the firm. 
Now, Don ruminates openly about death and the hereafter. His ad campaign for The Royal Hawaiian hotel, a crown jewel of Sheraton, alludes to heaven and paradise, but in ways that strike his clients as morbid. That Don latches on to the idea of shedding one's skin is unsurprising. He has done it many times himself - from assuming Lt. Draper's identity to his charade of suburban domesticity, down the rabbit hole of slightly lecherous divorcee and back to marital bliss, Don's entire persona is about reinvention. Now he has simply gone from ephemeral "handprints on glass = nostalgia"  to showing an equally fleeting image - of footprints in sand, leading out to a watery beyond. While Don may see poetry in his advertising imagery, in his personal life, there is no deftness to his fear of mortality. Don drunkenly harangues his doorman into telling him about his near death experience, demanding to know whether the doorman "saw" anything. When the doorman tries to clarify that he was never in fact "dead," Don demurs, claiming the man had in fact died.
Roger, on the other hand, has been touched by death directly. He had not one but two heart attacks  and opens this season coping with his mother's death. Long ago, when he and Don were contemplating the meaning of life, it was Don who spoke with a "you only live once" bravado that Roger interpreted as a green light to leave his first wife Mona for second wife Jane.  Now, Roger simply sees people out to pick his pocket. He quickly sizes up Mona and his daughter Margaret as running a scam to get him to invest in a business endeavor for son-in-law Brooks yet misses Jane's gracious gesture of offering back his mother's wedding ring. In therapy, as in life, Roger is, well, Roger - wise cracking and unserious, yearning for some deeper meaning he has searched for in the bottom of a bottle of Stolichnaya, the arms of younger lovers and LSD-soaked sugar cubes, and left wanting when no explanation satisfies him. In the end, it is the death of his shoeshine man that finally cracks Roger's exterior as he crumples in a heap in his office when handed the man's kit.
But if all of this brooding and heaviness felt disorienting, it was because so much of the show has changed from Easter to Christmas 1967. It was difficult to simply get your bearings as a sea change occurred in everything from the firm's architecture to the cast's wardrobe. Facial hair abounds - from Stan Rizzo's burly beard to Abe Drexler's channeling of a young Frank Zappa. Roger, until now impeccable in grey or navy three-piece suits, now dons a royal blue blazer and creeping sideburns. Pot is now smoked openly in the office and through Betty's quixotic trip to the East Village, we see the clear social and cultural divide that will tear the country apart. That this episode was framed around New Years 1968 seems deeply intentional. Instead of standing for something we typically associate a "new year" with - rebirth, a new start, opportunity - so much of The Doorway meditated on just the opposite - death, finality, and loss.
Indeed, the dissonance between "the world" and "the show" is what I found so difficult to follow on first viewing. Burt Peterson, last seen getting fired from Sterling Cooper at the beginning of Season 3 , has re-emerged as head of accounts at CGC. Random new characters appeared, their provenance, much less importance, entirely unclear. We are introduced to someone named "Bob Benson," a junior account man at SCDP, who may be Pete Campbell 2.0 or just someone who flitted into the show never to be seen again. Sally's friend Sandy may be the daughter of Betty's cancer-stricken friend , but whether she serves as a simple vehicle through which Betty more firmly embraces a darker persona (not to mention hair color) remains to be seen. Because the show demands investment by the viewer into these connections without knowing if they will pay off in deeper character development, The Doorway felt like sensory overload.
Meanwhile, another signature Mad Men maneuver added to the confusion. Storyline development "off camera" included the securing of the elusive Dow Chemical account, the firm's expansion to a second floor in the Time-Life Building and Megan's career advancement from a Butler Shoe advertisement to recurring character on a popular soap opera. Don and Megan have made friends with building neighbors Dr. and Mrs. Rosen and the window dressing of new copywriters at both SCDP and CGC may be mere fillers or turn out to become important supporting members of the cast. One never knows. 
In this swirl, Peggy Olson was the calm center. She is, as Ted put it, "good in a crisis," whether it's Abe's adverse reaction to vegetarian food or a client's concern about a negative association between an advertising campaign and the actions of GIs in Vietnam. The season premiere was Peggy's time to shine. She is a young creative director ("copy chief") already comfortable with both ends of the job - driving her underlings to come up with better ideas on the one hand and mollifying executives on the other. She even has time to keep up with Stan, and has, according to him, caught Ted's eye for something other than her ability to think on her feet.
As a set piece for Season 6, the two-hour season premiere felt more like a four course meal - deeply satisfying but leaving the viewer with that uncomfortable feeling of having eaten too much. Having inundated the audience with so much information for two hours, Weiner pulled a trick out of his playbook that harkened all the way back to the show's very first episode. There, as here, all was not as it seemed. In Smoke Gets In Your Eyes, we first see Don with Midge and assume she is his girlfriend or wife. It is not until the end of the episode that we find out Midge is his mistress and Betty his wife. In The Doorway, it is the opposite - we assume Don to be faithful until the end of the show, when we learn he is engaging in an active affair with Dr. Rosen's wife, Sylvia. But Don as an aging Lothario is a far cry from his swinging days of the early 1960s, when he casually told Rachel Menken that he was "living like there was no tomorrow, because there isn't one."  What was glib and flirtatious then, now seems foreboding and ominous, a sign of darker days ahead.
1. "When a man walks into a room, he brings his whole life with him. He has a million reasons for being anywhere; just ask him. If you listen, he will tell you how he got there; how he forgot where he was going and then he woke up. If you listen, he will tell you about the time he thought he was an angel or dreamt of being perfect and then he will smile with wisdom, content that he realized the world is not perfect. We are flawed because we want so much more; we are ruined because we get these things and wish for what we had." - The Summer Man, Season 4, Episode 8.
2. The Hobo Code, Season 1, Episode 8.
3. Shut the Door, Have a Seat, Season 3, Episode 13.
4. Nixon v. Kennedy, Season 1, Episode 12.
5. The Suitcase, Season 4, Episode 7.
6. Commissions and Fees, Season 5, Episode 12 and The Phantom, Season 5, Episode 13.
7. The Wheel, Season 1, Episode 13.
8. Long Weekend, Season 1, Episode 10 and Indian Summer, Season 1, Episode 11.
9. "It's your life, you don't know how long it's going to be, but you know it has a bad ending. You have to move forward, as soon as you can figure out what that is." - Six Month Leave, Season 2, Episode 9.
10. Out of Town, Season 3, Episode 1.
11. Tea Leaves, Season 5, Episode 3.
12. Allison spent more than two seasons as Don's secretary with little ado, slept with him early in Season 4 and was gone shortly thereafter. Conversely, Megan, who was the most minor of minor characters through much of Season 4, emerges in the last few episodes to become Don's second wife.
13. Smoke Gets In Your Eyes, Season 1, Episode 1.