Long time no see, eh? Admittedly, looking back on some of what I wrote about the series years back reads as somewhat cringe but that’s to be expected. A lot of dumb shit’s happened in the last decade. If you can’t be critical of your past self and trying to improve, what the hell are we even doing? Everything shall remain for posterity.

I haven’t sat down to rewatch the series as a whole since 2018. Even then, I fell off in Season 6– the whole Sylvia plotline felt so contrived to me (not to mention the goddamned awful wig the brilliant Linda Cardellini was stuck wearing), but as I’ve gotten older I’ve mellowed a touch. Usually when Don sucks shit in his personal life, at least cool things are happening at the agency to take the edge off.. but here, he’s all garbage.

Watching this show has always felt rewarding since it’s such a richly told story, and as I’ve gotten older, I’ve found more touching moments, more relatability. Fucking News at 11 sentiments aside, it still looks and feels flawless, sleek, current and nuanced. Timeless and ageless. Seven seasons of rich character work, insanely beautiful visuals, and very funny moments.

10 years out from the series finale, I keep turning the same thought over and over. What is the thesis of this story, what are we taking with us at the end? Do people really change, or are we doomed to repeat the same bullshit ad nauseam in an Edge of Tomorrow or Groundhog Day loop?

In Season 1, the late great Bert Cooper once told Don ‘By the time you hit 40, you’ve met every type of person there is’; when I turned 40 in 2024, you bet this thought rattled around in my head for weeks. There’s an iota of truth to that statement. I do believe some people change, but only in a way that directly benefits them; it’s not inherently selfish, but it’s human nature to have that be the One true motivator. Being an opportunist is a human trait, it’s how we stay alive.

At times, the show feels like an advertisement for the American Dream(TM) while exposing the deep decay lingering just beneath the surface of that ideal. Look at Joan and her garbage husband, look at how Betty feels.

After all, Don Draper himself is a polished advertisement for Dick Whitman, what he Could Have Been had his circumstances been different. Probably why nothing ever feels like enough to him when he has So Much. Each season chips away at his carefully crafted persona. The Season 6 Finale In Care Of has him glumly boozing at a bar as Band of Gold drones on the radio, a stark contrast to the opening scene of the series premiere, cool and polished Don no more. All of this mess culminates with an emotional meltdown during the Hershey meeting. You can only keep up the mask for so long.

lol oop

The next time we see him in Time Zones, he is adrift and alone: starting with the Don Draper cosplay on the flight to LA and his deteriorating marriage to Megan, then ending on a long shot of him shivering on his Park Avenue balcony awash in despair, dishevelled in his bathrobe. Is that all there is? Indeed.

image courtesy of Tom & Lorenzo

For me, this series has always been about that existential need to know oneself and all the grit that that mess entails. So many people meander through life going through the motions of What They’re Supposed To Do And Want (Peggy constantly calls this out) even if it does not feel right, and I find it exhausting to watch in my personal life. Happens all the time, the same cycle repeats as we get older. People will do whatever according to The Plan, even if that plan is horrifying; you know that people will do anything to alleviate their anxiety.

Watching Pete’s story unfold is a great example. A lot of his life looks glossy and blue blooded on the outside, and he has a nice ending (which he deserves IMO) after being continually cut down to size. His parents never supported him despite their illusions of wealth which were of course, illusions. In spite of all that it turns out he’s learned lessons and figured out a way to move forward in a productive way, and even though he idolises Don to the end, Pete will always have that edge over him. Pete’s grappling with and eventual personal rejection of his Insatiable Want and WASPy expectations ruined what he had in the first place with Trudy. But hey,

woof.

So what the hell did Don exactly need? He doesn’t know what he wants, but he is Wanting. As the series went on, I kept thinking of Rachel Menken. Well.. Rachel Menken Katz, RIP. Was she continually on Don’s mind like her sister implied? We even get a fur salesman coda in that midseason premiere, a weird David Lynch dream. What was Rachel offering him? She read him for filth and got on with her life, we love to see it. Later, Don writes “People tell us who they are, but we ignore them: because we want them to be who we want them to be“. Since Anna is the key to Dick Whitman, how can he exist in the wake of her death? And then the news of Rachel’s passing hits him like a Mack truck. Trauma bonds are a hell of a drug.

Speaking of important women in Don’s life passing away, I’d be remiss if I didn’t of course mention Betty. Betty had a hell of a ride, man. A complex character often hated by the dense men of Reddit, she is a gorgeous albeit difficult product of her time. She is isolated and married to a career loner, in a time when women were housewives and treated as children. Is it so shocking that she would lash out and have no idea how to process her own emotions? Marrying Henry and getting on a path to pursue a postgraduate degree in psychology showed real growth for her, and having that cut so short is heartbreaking.

Don’s dreamy vision of Rachel in the fur maybe foreshadowed Betty’s eventual demise, as she was also photographed in an ad for a fur coat when she was still a model.

In the very beginning of Season 1, Roger makes an offhand remark that psychiatry is ‘just this year’s candy pink stove’ in regards to housewives. Lo and behold, the Rye mansion Betty later shares with Henry has that exact little detail in their kitchen. She has a cancer diagnosis fake out, and then the terminal one— which means Don must confront his own bullshit from his motherless childhood with his own kids. Betty is a complex character, she struggles to find her voice and to be understood. I hate that she got cut down as she was on the right track. Overall, Betty is a product of her environment and breaking free of those expectations is remarkably difficult, even after your parents are long gone. But she did show growth. I often think of one of the final conversations we see her have with Sally.

B: “I’ve learned to believe people when they tell you it’s over. They don’t want to say it, so it’s usually the truth.”

S: “I’ll be with you. I won’t let you give up.”

B: “I know that.. and I don’t want you to think I’m a quitter. I’ve fought for plenty in my life. I know when it’s over. It’s not a weakness, it’s been a gift to me. To know when to move on.”

And hey, Don finally has a lightbulb moment in the series finale. His experience at the hippie retreat with Leonard reinforces Anna’s dead-on read of his unending sense of feeling alone interfering with his own happiness. Right before that he rings Peggy, “I never got to say goodbye to you”. If he could get out of his own way, things would be a lot easier. Ain’t that the fucking truth? And per usual, Don’s personal lowest points bring him great satisfaction professionally; that Coca-Cola hilltop ad and of course, the events of Shut the Door, Have a Seat. The back half of the final season shows the walls of 70s cynicism slowly closing in. McCann, corporate consolidation, and now fucking everything is owned by private equity. Or Unilever.

What does it all mean? Well, don’t be like Don, for one. Watching these characters evolve over the course of the series is a real treat, and rewatching is a richer experience as I get older. Personal evolution is vital and it is never a straight line. Grief and love are one in the same and neverending, but how we choose to cope is of the utmost importance.

And that’s that! See you soon.