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A History of Mad Men’s Planes, Trains, and Automobiles

Don Draper (Jon Hamm) - Mad Men _ Season 6, Episode 9 _ 'The Better Half' - Photo Credit: Michael Yarish/AMC
Photo: Michael Yarish/AMC

The new poster for the final batch of Mad Men episodes is here, and it features a determined-looking Don Draper driving off into (well, out of) the sunset. Matthew Weiner was predictably cagey about the exact meaning of the image, but he did tell Vulture that “there’s going to be a sense of motion” to the final chapter. Mad Men’s a show that wrestles with the fundamental idea of change — whether people change, what happens to us when times change, who’s responsible for resisting or inciting change. That ambivalence is reflected over and over again in MM’s odd relationship with transportation: car crashes, plane crashes, identity crises on trains. If you’re a character on Mad Men, for the love of God, stay put.

Season 1
We first see Don in a car at the tail end of the pilot, just before the surprise reveal that he’s actually a married dad and Midge is his mistress, not his girlfriend. The pilot actually makes a point of showing Don on the train and in the car, going away, away, away from Manhattan. When we see Don on a train in general, we know something is up: We next see him on a train in episode three, where an old acquaintance recognizes him as “old Dick Whitman.” Don’s stunned. So stunned, in fact, that later in the episode he drives aimlessly with Sally’s birthday cake, shirking his responsibilities and drunkenly parking himself at the train station instead of returning to her party. (Away, away, away.) In episode 12, we see in flashback our Don on a train along with the coffin of the actual Don, ignoring a young Adam, who swears he spotted his big brother. We see Don’s commute one last time in season one in episode 13, with Don trudging home, daydreaming that his family will be there waiting for him. They are not.

Don’s not the only one who should stick to walking. Betty has terrible car juju: In episode 2, she gets carsick, and then later crashes her car during a sort-of panic attack. In the season finale, she approaches Glen, who’s sitting in his mother’s parked car. They hold hands briefly through the window.

Season 2
Everyone’s car troubles continue in season two. In the season premiere “For Those Who Think Young,” Betty’s car breaks down, and she attempts to flirt with the mechanic to lower the cost of repairs; it turns extremely shady for a hot second, and Betty finds the moment both erotic and scary (which is how she finds a lot of moments). In “The Benefactor,” Betty and Don have dinner with Bobbi and Jimmy Barrett, and Betty cries in the car on the way home, even though she’s not fully aware of Don and Bobbi’s affair just yet. Which is too bad, since the affair puts those two in legit danger when Don drunkenly crashes his car in “The New Girl.” (Peggy has to pick Don and Bobbi up at a faraway police station. She diligently drives them back to the city.)

That crash might have been the worst of things if not for “The Gold Violin.” In that episode, we learn in flashback that Don was once a car salesman — and in fact, Anna Draper tracked him down at a dealership. Don decides to treat himself and Betty to a new car, and she’s thrilled when he presents it to her. But it doesn’t take long for something to go awry, and by the end of the episode, she pukes, right in the front seat.

Don has a few other car scenes in season two: He jumps in the car with the spacey, alluring Joy in California, ditching all his meetings and confusing everyone he leaves behind. He takes a bus to see Anna, and in “The Mountain King,” tells a group of guys tinkering with hot rods he’s looking for work. He’s not, or not really, but it’s not clear to whom he’s lying: those guys? Us? Himself? Everyone all the time?

Season two has two other major transportation moments: In “Flight 1,” Pete learns that his father has died in a plane crash. There’s a significant amour of airline talk at Sterling Cooper — about Mohawk in particular, but they also work on American, and chat about air travel frequently — so of course Pete’s topsy-turvy about how to present himself professionally in the wake of his father’s death. (He mentions it in a pitch, which does not go over well.) Beyond Pete’s literal reaction, though, there’s something very abstract about a plane crash, especially as portrayed here: Pete et al. learn of the crash on the radio, and people are already making jokes and being crass by the time he gets a phone call telling him his father was on the flight. We see people die on Mad Men not constantly, but at least a few times, and if the show for some reason had wanted to do a “Pete sits vigil at his father’s deathbed” kind of story, that wouldn’t be so impossible. Instead, there’s something more unpredictable, ominous, and alien about a plane crash, baffling and closure-proof.

We see one other notable car scene in season two, though it’s a parked car, so the danger of the enterprise feels less imminent. It’s in the fourth episode, “Three Sundays,” and Father Gil has driven Peggy to the subway station. They sit for a moment, and he asks for some advice delivering his first Palm Sunday homily. It’s an odd moment for Peggy, who’s still struggling to get everyone at Sterling Cooper to give her even a shred of the respect she deserves. She’s the odd woman out in her family, and she’s pretty clearly not into church. But Father Gil likes and admires her, and his genuine plea for assistance in this moment winds up being a turning point for Peggy. In this episode, it’s still not clear exactly what the deal is with Peggy’s baby — maybe he’s being raised as her nephew? But in the following episode, as Peggy dutifully assists Don and Bobbi Barrett, it’s like she’s finally comfortable enough in her new self to acknowledge (to us in the audience, but to herself, too) what happened at the end of season one. Her nephew’s her nephew; her child was placed for adoption. Clarity!

Season 3
Season three practically opens on a plane: Don and Sal are traveling to Baltimore, and they flirt with the flight attendants. Well, Don does, and Sal plays along. Later at their hotel, Sal is accidentally outed when a fire alarm goes off and everyone flees. On the flight back, Sal briefly panics when Don asks for a moment of real honesty — but it’s about a possible slogan, not Sal’s closeted sex life. “Limit your exposure,” indeed.

It’s not that only bad moments happen in transit; it’s more that many pivotal moments do. In season three’s “The Arrangements,” Grandpa Gene recklessly lets Sally drive his car. It’s a dumb idea, yeah, but it’s probably the highlight of her life, and while Grandpa Gene’s seems like the turning point in Sally’s childhood, it might actually be taking the wheel while her brother jealously whines in the back. This is the first time an adult has trusted and encouraged Sally. Grandpa Gene actually likes Sally, and that’s a big shift for her, away from two parents who have so much of their own baggage they can barely remember to feed her dinner.

A lawnmower isn’t really a mode of transportation, but: the lawnmower. “Guy Walks Into an Advertising Agency” is set several months before the Kennedy assassination, but for Mad Men, this is really when the cultural entropy starts in earnest. The following episode has Don getting jumped by the hitchhikers he picks up; it finds Betty beginning her romance with Henry Francis in earnest; somehow Duck seduces Peggy. That’s all in one episode! The wheels have come off the wagon. Well, the foot has come off the British guy, at least. Things are getting tense.

In “Wee Small Hours,” we see Don in his car again, this time with Miss Farrell; the two listen to a radio broadcast of the “I Have a Dream” speech. Don later drives by that same spot, hoping to accidentally-on-purpose run into her again. In “The Color Blue,” Don’s train ride again becomes a neither-here-nor-there place: Suzanne gets on the train to surprise him and have a conversation, which is both clandestine and completely public. She convinces Don to drive her brother somewhere and he agrees, only to later drop said brother elsewhere, per brother’s request. At the end of the episode, several characters have here-but-not-here moments in the back of their respective cars: Roger’s mother mistakes Jane for Margaret; Lane’s wife is thrilled but Lane is crushed that they might move back to England; Betty rides with Don without telling him that she’s discovered his secret locked drawer. She doesn’t confront him until “The Gypsy and the Hobo” — a confrontation that happens while Suzanne is outside sitting in Don’s car.

JFK gets shot. While in a car.

And finally, how do we know for sure that Betty and Henry Francis are going to wind up together? We see them, on a plane, en route to Reno.

Season 4
Our first car scene is in the season premiere, “Public Relations.” Don and his date Bethany are noodling around in the back of the cab, and she politely and genuinely declines to take things further. We see the flip of this with Betty and Henry, hooking up in their car while it’s parked in the garage. Ah, bench seats. The couples are presented again in car-by-car make-outs later in the season in “The Summer Man,” this time with Betty and Henry fighting bitterly, while Bethany goes down on Don in the back of the cab. To everything there is a season. Don hooks up in yet another cab later in that episode, this time with Dr. Faye; notably, he’s the one who decides to take things slow in that instance, because he seems so taken by her.

Don visits California again in “The Good News,” and we see him on a plane, which is the kind of filler shot Mad Men wouldn’t bother with unless it meant something — we know how people get from New York to California. But plane travel on the show lets people reestablish identity. As he heads to California, Don decides to be Dick, of course. He even rents a red convertible, though maybe that turns him back into Don, since he scams on Anna’s college-age niece while driving her home. The transformation back into full Don is completed on the plane ride home, which occurs on New Year’s Eve. What’s your resolution, Don?

Transit moments in season four are often about negotiation, which becomes codified in “The Chrysanthemum and the Sword,” an episode about negotiating (or not) with Honda that uses a sporty motorcycle as part of the mind games against Cutler Gleason and Chaough. Around and around and around Peggy rides, just on a soundstage, not doing anything or going anywhere, except it’s Peggy — she’s always going somewhere.

Joan has a moment of self-negotiation in “Hands and Knees.” She’d gone to Morristown to have an abortion, but after a jarring encounter in the waiting room, where another woman assumed Joan was the mother of a teenager, she changed her mind. It’s not clear in the moment that she did, but we learn later she did not have the abortion, so the scene of her on the bus is a quick glimpse of how she’s telling herself the story of what just happened. She’s sitting there by herself, just like she went by herself to that doctor, just like she’s going to raise her baby more or less by herself, since she’s married to such a dipshit, and she can’t exactly run off with Roger. It’s a brief scene, but in that quick shot we can see Joan decide how she wants to be: She’s sad and scared for a second, and then excited, determined, a little bit happy.

Peggy, too, is happy, in the back of Joyce’s car, sitting on Abe’s lap in “Chinese Wall.” Betty’s pretty unhappy when she drives up and catches Sally hanging out with Glen Bishop in “Blowing Smoke.” Is this me? they both wonder. For Peggy, the answer’s a giddy, vaguely horny yes — yes, she’s into a romance; yes, she’s into left-wingers. For Betty, the answer’s a lot less clear: Betty’s jealous of Sally, which is something she’s unable to acknowledge or understand; she’s on the one hand proud of herself because she sees this as an instance of appropriate mothering, but she’s also frustrated because …well, why is Sally like this in the first place? (Oy, Betty.)

Season 5
So we’ve seen crisis, alienation, maturation, and negotiation. Season five’s transit attitudes — and season five, generally speaking — are about identity. It starts early, with Lane finding someone’s wallet in a cab. He becomes intrigued by a photo of a woman in the wallet, because everything in Lane’s life is feeling particularly difficult. Don purposefully leaves Ginsberg’s drawing in a cab in “Dark Shadows,” as a way of reaffirming his place atop the idea pyramid. There’s more identity revealing in “Tea Leaves,” when a stoned Harry Crane reveals — by housing a bag of burgers — just how immature he is. (This, moments after Don and Harry mistake another group of guys for the Rolling Stones.)

In “Signal 30,” Pete’s in a driver’s ed class — if there’s anyone who needs to learn about having an identity, it’s Captain Weaselthoughts, who could use a new one. (This is the episode where Lane smacks him.) Don is trying so hard to be the father and husband he never was before, and in the car with Megan, on the way home from a torturous dinner party at Pete’s, Don pulls over and asks to “make a baby.” Change does not come easy, but maybe just for this moment, this car ride, this one sex act, Don can actually be who he thinks he’s trying to be. Because in “Far Away Places,” he tries to construct Megan’s identity for her, too, which she’s not interested in. They can drive away, he tells her; she’s the boss’s wife! Isn’t that great? She’s unmoved, and she falls asleep. Later, they have a huge fight at Howard Johnson’s, and Don drives off in a huff, leaving Megan behind. Is that who he is instead?

The second half of season five gets to the grittier, more shameful sides of identity. In “Lady Lazarus,” Pete becomes his worst self in transit. He can be a real piece of work at the office, but his behavior here is even more devious and cruel. On the train, he bumps into an acquaintance, Howard, who brags that he’s got a mistress in the city. Pete winds up seducing that guy’s tragic wife, Beth, by driving her home. They have sex, and then Pete gets back in his car, trying to transition from “guy who cheats on his wife with a very unstable woman” to “guy who just goes home.” Back on the train, Pete wrangles a dinner invite to Howard and Beth’s, so unable is he to see himself and his actions clearly. One night at the train station, Pete sees Beth, and she draws a heart on her car window. We see Pete and Howard on the train together a few more times, each as rotten as the last. They get in a fistfight on the train in “The Phantom,” because Pete sees himself as Beth’s gallant protector. (He is wrong.)

Speaking of rotten, remember Jaguar? Don and Joan are at a Jaguar dealership in “Christmas Waltz,” pretending — easily — to be a married couple considering a car purchase. Don pays off the salesman so he and Joan can take a test drive just the two of them, and it’s the ominous start of Joan’s performances for Jaguar-related purposes. All things Jaguar wind up being more or less poisonous for the rest of the season: Rebecca Pryce buys a Jaguar in “Commissions and Fees,” and that becomes Lane’s breaking point. He tries to kill himself with that car, and when that doesn’t work, he goes to the office and kills himself there. There’s a part of Don that blames himself, and that’s the part that offers to drive Glen Bishop back to Connecticut, and then to let Glen take the wheel for a bit. In this car, Don is the kind of guy who grants wishes. He makes people happy. He encourages people to joyfully enjoy control of their own lives. That feels good, that feels right, that feels like a thing Don wants to do and be. But it doesn’t last. Nothing does.

Season 6
In season six, that inability to last is a failure, and we see instance after instance of shortcomings, even tragedy, tied to vehicles. It starts with Betty getting a ticket in “The Doorway,” relatively minor until her mother-in-law tries to pull strings. In “To Have and to Hold,” Joan rides in a cab with her old friend Kate and some skeezy dude who kisses them both, which is not inherently mangy but certainly is here. Don’t do it, Joan! Don and Megan, also in a cab, joke about the couple who wanted to swing with them, but as Don laughs along, he’s also massively lying. He’s cheating on Megan, and we know he is, and while she’s finding this exchange hilarious and endearing, we know it’s the beginning of the end. It’s a failure, this conversation. This marriage.

Ted Chaough flies his own plane in “Man With a Plan,” and while it’s a success for Ted, it’s another knock against Don, whose apprehension and queasiness give Ted the upper hand. Don’s the guy whose virility makes everyone feel safe and protected — until now, when suddenly he’s the guy sweating and kind of freaking out. Then comes “The Crash,” where Ken loses an eye. And everyone hates the car Harry rents in “A Tale of Two Cities.” Stupid Harry.

“The Quality of Mercy” gives us precise shortcomings from both Sally and Betty. As Betty tries to be enthusiastic about sending Sally to a very fancy boarding school, Sally’s surly and pouty even though she’s getting what she says she wants — which is to be away from Betty. Betty’s not a good mother for a number of reasons, and on the ride back from the school visit, that’s brought into relief: She raised Sally to be just like she is, which is basically a tragedy. She lets Sally have a cigarette, which is bad, too, though not as bad as raising someone who doesn’t know what healthy love feels like.

The transit failures start piling up in even sillier fashion. Pete’s mother allegedly falls overboard while on a cruise. Pete wrecks a car in a showroom for Chevy, the client they’ve been wooing so ardently. Don drives his kids to see the rickety brothel where he grew up, because that seems like a really stable thing to do. Crash, crash, crash.

Season 7
Change is bad, and change is inevitable. We’re not who we think we are, but we’re trying. Be yourself, but God, please be a better version of it. The first half of season seven uses transit as a measure of will: How far will we go? In “Time Zones,” Don flies back and forth, a lot, to California. So often that he’s literally in the passenger seat with Megan picking him up from the airport. That’s a far reach for our Don. Even farther, though, is the end of his car ride with Sally in “A Day’s Work.” After a pretty rough weekend, Don drops Sally off back at school, and without any pretense, she looks right at him and says, “Happy Valentine’s Day. I love you.” That’s a stretch for both of them — maybe not to feel it, but certainly to say it. Ted is in such a state of despair that he cuts the engine on his plane just for a moment, but enough to scare the crap out of his Sunkist passengers.

How far will we go? To the moon and back, “Waterloo” reminds us. The value of human endeavor lies in the actual endeavoring. Don and Peggy and Pete and Ted, Sally and Betty and Roger and Harry, Joan and Dawn and Bert: We’ve seen everyone have a moment where they think, Why am I even trying? And on their trains and buses and cars and motorcycles and rocketships and planes, the answer is because I have somewhere to go.

Mad Men’s Planes, Trains, and Automobiles