TV Database Mad Men (2007)

"But what is happiness? It's a moment before you need more happiness. I won't settle for 50% of anything. I want 100%."

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The last time we saw Don Draper in season five, he was nursing a drink at a bar (while Megan's nearby shooting a commercial) when a blonde stranger approached him with a loaded question: "Are you alone?" The answer he gave then is the same one he gives now, without even realizing it — spiritually, Don remains alone.

It’s December 1967. America is knee-deep in Vietnam, counterculture is detonating across the cultural landscape, and anyone with a functioning nervous system is either rebelling, numbing themselves, or trying to sell you a beautifully packaged version of both. Mad Men distills that free-floating dread and pours it down your throat with a Hawaiian sunset chaser, a fleeting, burning glimpse of the paradise that slips from your grasp.

And where does that leave our protagonists at the dawn of this so-called new world? Still fumbling for a doorway that never really existed.

Don’s reading Dante's Inferno on a beach in Waikiki, which might be the most Don Draper thing Don Draper has ever done. Megan, meanwhile, is reveling in the high of her soap opera fame, thrilled at the smallest public recognition even as she begins to feel the insignificance of her career creeping up. Her once-supportive husband is already miles away behind his shades, dead-eyed and disinterested. Even in paradise, Don can’t stop himself from drifting, officiating the wedding of a drunken soldier he barely knows — Private Dinkins, a walking specter of Don’s buried past — and unknowingly bringing home a Zippo lighter inscribed with the kind of brutal wisdom that could be carved on Don’s tombstone: "IN LIFE WE OFTEN HAVE TO DO THINGS THAT JUST ARE NOT OUR BAG."

Betty, for her part, is an unfiltered menace. She fires off one of the most psychosexually deranged jokes ever aired on television history over her daughter's underaged friend, pivoting with stunning speed back into "concerned mother" mode. Her scenes with Sandy are brutal little dioramas of Betty’s eternal crisis — the push and pull between wanting to nurture and wanting to annihilate anyone who embodies the youth, freedom, and possibility she knows she squandered. Sandy represents everything the emerging counterculture promises: independence, meritocracy, rebellion. Betty is the tragic relic trying to persuade the next generation to sit politely at the same broken table she once admired, being the complacent and faithful wife to a patriarchal society even as she throws tantrums at it. You can see, in every bitter line reading, just how deeply Betty resents that the world is changing — and that it’s leaving her behind. And yet, brutal as Betty's bitterness might be, she’s not entirely wrong. There's a breathless naivety in Sandy’s romantic vision of communal living — a fantasy of democracy and freedom that wilfully ignores the riots, robberies, and harsher realities Betty has already lived through. Even as Betty fights against the future, she knows better than to believe in fairy tales.

Peggy, by contrast, is on the rise — or at least giving the impression she is. She’s finally her own boss at Cutler Gleason and Chaough, barking orders with the weary confidence of a woman who has seen too much and expects worse. But the higher she climbs, the heavier the air gets. When an off-color joke on The Tonight Show derails her Koss headphones campaign (Vietcong ears accessorized as grotesque trophies by American soldiers), Peggy faces a grim lesson: creative freedom comes handcuffed to creative responsibility. Even as the counterculture feminism of the era opens new doors for women like Peggy, the brutal irony is that the same "free speech" she might have once championed comes back to bite her career in the throat. Her progressivism, like so many ideals in Mad Men, feels sturdy until it cuts into her bottom line.

Meanwhile, Roger Sterling is unraveling in slow motion. His therapy sessions, all dry wit and manufactured detachment, peel back just enough to reveal the void underneath. In his monologue about doors and bridges — about how life is supposed to change you, but doesn’t — Roger all but delivers the episode’s central thesis: experiences don't transform you; they simply accumulate, like loose change jingling pointlessly in your pocket as you march toward oblivion. So when news of death in the family hits, we get the clearest look yet at a man who’s realized he can’t charm or drink his way out of mortality. The death isn't tragic so much as inevitable, and Roger reacts accordingly: with numbness, confusion, and a desperate need to feel something — anything — before the void swallows him, too. Everything in life, every supposed milestone, is just another door swinging shut behind him. No matter how many times Roger tries to reinvent himself — lover, husband, boss, philosopher — he’s still stuck on the same unchanging track to nowhere. And for once, even Roger Sterling can't laugh it off.

Even the newcomers, like Bob Benson — all shine and forced optimism — carry the faint whiff of desperation that hangs over SCDP like stale smoke. He presses too hard to impress Don in the elevator, but what he's really selling isn't himself — it's the hollow promise that enthusiasm still counts for something in a world that's quietly rotting from the inside out.

By the time Don stands frozen for the photographer, lighter of another man’s war in hand, while being urged to "just be yourself," the bitter irony crystallizes: which self? The ad man? The deserter? The absent husband? The scared, hollow boy from Illinois? The man who still clings to the idea that if he walks through enough doorways, he’ll eventually find the one that leads to salvation?

"The Doorway, Part I" doesn’t offer any answers — it only deepens the questions.

And that’s what Mad Men has always done best.

"People will do anything to alleviate their anxiety."

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When my father died a year ago — heart attack, sudden, brutal — we didn’t even realize until 30, maybe 40 minutes after. Just... laid out on the floor. It’s an understatement to say my relationship with my parents was strained. Growing up in the '90s as a Singaporean Chinese boy basically meant you got the full brunt of the Asian Parenting Discipline Kit™ — rattan canes, shame as a weapon, and the occasional reminder that your gender was a disappointment. I still remember my mother muttering that she should’ve given birth to a more compliant daughter. Real confidence booster, that one.

Point is that when my father passed, I didn’t cry. Didn’t feel shattered. Mostly, I was afraid he’d come back to haunt me, fueled by Chinese superstition and guilt. But nothing happened. Time just moved on, quietly, mercilessly.

In some ways, watching The Doorway, Part Two, I saw that same quiet numbness reflected in Roger Sterling — and in almost everyone else. There’s this unspoken fear: "Is something broken in me because I’m not feeling the things I’m supposed to feel?" And in true Mad Men fashion, the show doesn't answer the question. It just lets it hang there, bleeding out slowly.

If Part One was existential dread in Hawaiian sunlight, Part Two is the silent, spiritual death that follows. Nobody's falling down weeping dramatically. Instead, death lingers like a fog — a smell you can’t quite wash off. Sometimes obvious, but mostly just there, soaking into everything.

Character arcs this hour all revolve around that rot creeping in, some more quietly than others. Don for example, bless him, is trapped deep in his own anxious spiral — trying to alleviate his dread the only way he knows how: distraction, control, self-destruction. There’s a self-loathing to him that’s thicker than ever, but Mad Men plays it so subtly you almost miss it until that subconscious desire for another doorway that will never come bleeds into his work. Suddenly, there he is, staring off into space with that signature Jon Hamm emptiness. He’s a man with everything he once thought he wanted — a wife, a career, respect — and yet you can practically see the walls closing in around him frame by frame. For this is season 6 — he can't just escape anymore, he's tried that routine. So now he's stuck in his Inferno, crawling through the Nine Hells of this season, finding himself amidst the dark woods. Every choice he makes this hour is about delaying the inevitable, kicking the existential can just a little further down the road.

Meanwhile, Betty is... surprisingly hardy this hour. Not hardy like a Strong Independent Woman™ — hardy like nerves of steel, scraped raw, sharp around the edges as she crawls her way back into humanity. I never hated Betty before (even if her parenting skills made my inner child flinch), but I never really respected her either — until now. And while the wildly inappropriate "joke" she made in Part One leaves a nasty aftertaste, here in Part Two, when she’s faced with real-world grime and danger, Betty doesn’t flinch. She steps right into the mess. And you realize — maybe all that armor wasn’t about vanity. Maybe it was about survival. It's almost as if she’s channeling some deep-seated aggression she’s never allowed to voice. She’s supposed to be happy with Henry Francis, but something still itches under her skin, a purulent wound she has to scratch even if it wouldn't heal. Betty’s war isn’t with the world anymore. It’s with herself.

Roger, though, is the star of the existential parade here. His whole "nothing matters, life is just pennies on the floor" speech isn't edgy nihilism — it’s a man trying desperately to hold onto something before he turns into dust right in front of us. His cool, sardonic mask — the one he’s worn like armor since Season 1 — finally starts to crumble. When the grief finally cracks through his perfect silver-haired mask, it’s almost unbearable — not because it’s loud, but because it’s small. It’s real. It’s ugly and raw. It’s the kind of private breakdown you never show anyone if you can help it. It’s also some of John Slattery’s best work on the show, no question.

Peggy is perhaps the odd woman out in our morbid episode. She’s got momentum, drive, optimism — hell, even a little joy. But it’s bittersweet, because you can see how much she’s becoming Don Draper Lite with all of his worst habits, whether it's barking at subordinates, sacrificing everything for the pitch, or mistaking exhaustion and fear for inspiration. There's a tunnel vision there that blinds her to everyone around her, and she's winning for now, sure — climbing the ladder on her own terms — but every step upward feels like it costs her a little more of herself. The air’s thinner up there, and it’s starting to taste a lot like ash.

Bob Benson also slithers into the frame more noticeably now, and it’s amazing how fast you want to punch that smile off his face. He’s the kind of guy who would bring a "Get Well Soon" card to a funeral if he thought it might get him promoted. And when even Ken Cosgrove — Ken Cosgrove, human Labrador retriever — has to tell you to sit down and shut up? You know you’re overplaying your hand.

Thematically, it’s no accident that death — both literal and spiritual — is front and center this season. Given what’s coming historically in 1968 (no spoilers, but let’s just say not a great year for America), Mad Men opening with death hanging over everything feels right. The show isn’t just chronicling a time of cultural collapse. It’s chronicling personal collapse too — all the ways people rot slowly before history even gets a chance to wipe them out.

Yeah, sure, the symbolism is getting a little heavier-handed than it used to be (we get it, Weiner. Doorways. Infernos. Baptism water that looks suspiciously like a jar of granny's peach tea from BvS), but honestly? I don’t mind. The show has earned the right to underline a few things by now — and it still gives you plenty to chew on without spoon-feeding anything. Plus, I just find it easier to discuss these themes when they are laid on this thick. Gives me something interesting to talk about in my reviews.

The Doorway, Part Two doesn’t offer catharsis. It offers a slow, creeping realization that time is devouring everything you love, and you’re just supposed to keep smiling and selling yourself anyway. It’s beautifully ugly, and somehow, it still leaves you wanting more.

This is Mad Men in full decay mode — and it’s glorious.