I should preface this piece by saying that's it's written under (mild) duress. My editors asked me to choose a favorite Mad Men episode, and for a long time, I resisted because the series is so wide-ranging in its goals and operates in so many different modes. My short list might include season one's "Babylon," "Nixon vs. Kennedy," and "The Wheel"; season two's "The Mountain King" and "Meditations in an Emergency"; season three's "My Old Kentucky Home," "Shut the Door, Have a Seat," "The Grown-Ups" (officially the JFK episode), and "Guy Walks Into an Advertising Agency" (which works through the JFK assassination obliquely and symbolically); season four's "The Chrysanthemum and the Sword," "The Summer Man," and "The Suitcase" (a classic, obviously, yet not emblematic of the series from week to week); almost any episode from season five (the most cohesive and ambitious overall, as far as I'm concerned, basically one 13-hour episode or movie, though "The Other Woman" stands out, as "The Suitcase" did in season four); season six's "The Doorway" (parts one and two), filmmaking-wise, a little masterpiece; and season seven, part one's "Waterloo" and "The Strategy."
And maybe it goes without saying that if I had written this preface last week or next week, my short list would be different? I hope so.
All that said: If I were to pick one Mad Men episode to show to people who've never seen the series but want to get a sense of what, in a very broad sense, it is, I'd pick "The Arrangements" from season three. It's a relatively quiet episode, and not one that's thought of as a milestone in any creative or dramatic sense. But it's intelligent, heartfelt, and complex, and I think about it all the time.
Written by Andrew Colville and series creator Matthew Weiner, and directed by Michael Uppendahl (who has directed many signature episodes), it's a great example of Mad Men's ability to operate on several different levels and make several different points about many different things, and somehow make them feel coherent without distorting, omitting, truncating, or otherwise mangling any individual element. It hangs together in the manner of some of the best American literary fiction from that period. Expertly shaped and paced, "The Arrangements" just sort of glides along on a vibe, casually deepening some of the show's key themes (including the persistent but low-level fear of death that hangs over every adult character's life, and the profound influence that parents have on our personal development, and their anxiety about that influence) while always seeming as though it's not trying to make or score any particular points, just watching the characters be.
At the heart of the episode is young Sally Draper's relationship with her grandpa Gene, who's moved into the Draper house during a particularly tense and awkward period of Don and Betty's relationship. Gene is one of the most realistic grandparents we've seen on television. He doesn't have much screen time, but he's one of the show's most vivid and emblematic characters. He simultaneously represents retrograde viewpoints that are gradually ebbing (in social respectability, if not existence) and basic feelings toward children, grandchildren, and family that have always been a part of life and always will be, no matter how evolved we become or how evolved we think we've become.
Like a lot of older relatives, Gene seems to view his grandchild as an opportunity to do the parent thing again and get it, if not entirely right, then at least somewhat more right than he got it when he was raising Sally's mother Betty. He dotes on Sally and truly listens to her, and seems to get her on a much deeper level than her mother, maybe in some ways more deeply than her father (with whom she has a much more natural bond). There are moments in the episode where Gene seems to instinctively understand who Sally is now and what she might someday become, then tell her what she wants and needs to hear (the most inspiring, surprising moment is when he tells her, in effect, that she can be anything she wants to be, a sentiment we've never heard Betty or Don express to Sally with such directness). At the same time, though, Gene has that older relative's tendency to just blurt out whatever's in his head, even if it's petty and cruel toward Sally's parents and fills her head with emotional toxin.
You get the sense that Gene is trying to rectify mistakes he made with Betty, and perhaps evolve himself through his relationship with his granddaughter. You get a sense of how he and his late wife might have infantilized Betty in the scene where he attempts to talk to her about his will and funeral preferences, and she can't even go there. "I'm your little girl," she says. "Can't you keep it to yourself?" She seems mere moments away from plugging her ears and singing, "La la la la, I can't hear you."
But even though he's clearly trying in all sorts of ways to be better than he's been in the past, Gene is also a flawed human being, not a plaster saint. He lacks self-awareness and self-control. So at the same time that he's trying to say and do the right things, the "evolved" things, he can't resist the opportunity to score points off Betty (with Betty herself, or through his conversations with Sally). And there are moments when he gives "life lessons" that seem like poor lessons indeed, like when he goes through that box of war memorabilia with little Bobby Draper in the kitchen, puts a Prussian soldier's helmet on the boy's head, and unironically repeats the canard that war will make a man out of him.
Don's reaction to the latter conversation is note-perfect, not just because it's so ambivalent but because — like so many other scenes in the episode — it extends this "anxiety of influence" notion to other characters and relationships. Don is a Korean War veteran who not only witnessed horrific violence on the battlefield but secretly stole a dead man's identity in order to remake his own. He harbors a more skeptical attitude about war, especially as a crucible of manhood, and he warns Bobby to take off the German helmet that Gene has placed on his head by way of bonding with him, because it's a dead man's helmet and it "belonged to a person." Don's quietly agonized reaction throughout this scene will ring true for any parent who's ever tried to assert his or her values over a grandparent's while trying not to diminish, offend, or otherwise upset the grandparent — much less signal to the child that there's tension between the adults in the room, or that grown-ups might have different points of view on what sorts of values one should pass on to the youngest generation.
We see this anxiety of influence theme in other scenes as well, including the ones where Peggy decides to move out of her parents' house and get an apartment in the city. We get a very clear sense that her values don't sync up with those of her second-generation Norwegian immigrant mother (or her sister, who accommodates/indulges their mother and tries to broker peace between them). Peggy's mother is even uglier to Peggy than Gene is to Betty. "You'll get raped," she tells her in their final scene together, "you know that." But as is so often the case on Mad Men, we realize that her ugliness can't just be written off as cardboard villainy. We might not feel sympathy for her, but we should feel empathy. She's lashing out from a place of parental love and affection, as well as deep insecurity about not being needed anymore and having her personhood rejected along with whatever values Peggy can't abide.
The scenes between Peggy and her mother are exquisitely painful because, like the scenes in the Draper household, they are true to what we've experienced in our own lives. We can see that Peggy is trying to honor and placate her mother at every point along the way. She even tries to soften her up by giving her a TV, and of course her mother rejects it when Peggy announces that she's moving out. It's not just the moving out that hurts. That television represents the success Peggy's had in her chosen career, her comfort with the mid-century "modern" world of the ’60s, and the glimmers of feminist autonomy that are shaping and guiding her choices, though Peggy herself only sometimes realizes what's happening in her own mind. All these aspects of Peggy's identity are anathema to Peggy's mother, who, in earlier episodes, has embraced and promulgated the idea that a woman's highest goal should be to find a nice man, get married, and have kids. One of the great terrors of many parents' lives is that their children will repudiate what they stand for and have spent their lives believing. It's not merely a rejection but a negation — or at least it can feel that way; a patricide or matricide in miniature. Peggy is dead to her (for the moment) because she feels as though she's dead to Peggy.
All the strands in this episode tie back into self-definition and the anxiety of influence, though subtly enough that you don't feel that you're watching a pianist hammer the same note in different octaves. Children always have to separate from their parents and somehow define themselves against, or apart from, their parents, otherwise they can't make their own way in the world. But it's a painful, inexact, often clumsy process — purposeful but also reflexive and unthinking, full of intentional and unintentional inflictions of distress, and gestures that are meant to heal but wound instead.
Peggy's attempt to find a new roommate is one example: She posts a "roommate wanted" sign in the office that prompts her co-workers to prank-call and humiliate her, and Joan steps in to give Peggy some words of wisdom and convince her to seize the moment and present a vision of who she'd like to be. "This is about two young girls in Manhattan," Joan says, making literal the idea of writing one's own narrative in life. "This is about an adventure."
She adds, "Everybody knows you here," to dissuade her from advertising for a roommate in the office. This, of course, is one of the reasons Don Draper, a.k.a. Dick Whitman, left home and became, in more than one sense, a different person, and why anyone leaves their parents' house, or their hometown, or adopts new attitudes and has new experiences. This happens in every culture, but in the United States, it's at the center of our national mythology, and Mad Men comments on this as well by centering so many of its subplots on the children and grandchildren of immigrants, or on outsiders of one kind or another (including Jews, African-Americans, Italians, and gays) who never feel embraced by the dominant culture but can't live outside of it, and must, therefore, find a middle way.
Sal, the hardworking wizard from the art department, is a double outsider (Italian and in-the-closet gay, unhappy in a heterosexual partnership); one of the funniest and most incisive scenes finds him acting out an ad modeled on the one-take opening of the film Bye Bye Birdie for his spouse, Kitty, who gradually realizes that her husband is gay when he comes alive as he acts out the number for her. We don't know anything about Sal's parents at this point, but in a sense, we don't really have to: The straight-male culture of Madison Avenue is the de facto parental influence whose approval he's trying to win, even as he channels sensibilities that would horrify them if he were to express them openly. The ad is superb, and executed exactly as the client requested, yet they still reject it. Why? Roger's theory: "It's not Ann-Margret."
Along similar lines: The other client of the week, Horace Cook Jr. (a.k.a. "the fatted calf"), wants to drop a million dollars on the agency to turn his pet sport jai alai into a sensation in America. We learn he's doing this to prove to his moneybags father that he's not just a spoiled rich kid who never had to work a day in his life — that he can achieve something apart from his old man, albeit with millions of dollars passed down from that same old man. And yet his ultimate dream is to present his dad with the gift of a winning team as a birthday present — a marvelous touch that drives home how children often try very hard to establish an identity apart from their parents so that they can ultimately win their approval and be forgiven and embraced for any real or imagined offenses against authority. There's a sense in which every major character is playing out a different version of Peggy giving a TV to the mother who doesn't approve of the parts of her identity that made it possible for her to afford a TV. We don't want to be a part of clubs that wouldn't have somebody like us as members, but there's also a part of us that wants to be welcomed back into the club on our terms.
The process plays out in various ways, and through various characters, throughout the run of Mad Men, and it often feels like a microcosm of what's happening in America as a whole, with newer generations separating from and defining themselves against older ones (the book that Sally reads to her grandfather is, of all things, The Decline and Fall of the Roman Empire), yet often living out new versions of old patterns without realizing that they're doing it. We want to find our own identities, but we're driven by the forces that made us whoever we are at the moment of attempted self-definition, and that limits our ability to act clearly and think clearly, and sometimes leads us to take one or two steps back for every step forward — or run in place.
"The Arrangements" gets at this profound emotional messiness not just in scenes of grandparents, parents, and children interacting, but in scenes of people laying the groundwork to become somebody new or different, out of earshot of the people whose influence they're trying so hard to neutralize or escape (Peggy with her roommate ad, or Horace Junior in conversation with the creative team). It is in every way a quintessential Mad Men episode, never more so than when Don digs into keepsakes from his actual childhood and silently regards photos of his father, Archie, and his stepmother, Abigail. He rejected them, ran away from them, negated them, but they're still a part of him.
Correction: A previous version of this piece mistitled the season two episode, "The Mountain King."