Don Draper is a mess. By the time we hit the start of Mad Men Season 4, the suit is still sharp, but the guy wearing it is basically a hollow shell. Everything is different now. The old agency, Sterling Cooper, is dead and buried. The marriage to Betty? Torched. Don is living in a depressing, dark apartment in Greenwich Village, coughing through Lucky Strikes and drinking way too much rye alone.
It's glorious.
Most TV shows lose steam by their fourth year. They get lazy or start repeating the same old tropes to keep the advertisers happy. Matthew Weiner did the opposite. He blew up the foundation of the show. He moved the action to a cramped, chaotic office in the Time-Life Building and stripped Don Draper of his suburban safety net. This is the year the show stopped being a period piece about "the way we were" and became a brutal study of what happens when you get everything you wanted and realize it’s not enough.
The Chaos of Sterling Cooper Draper Pryce
Starting a new business is hard, and Mad Men Season 4 doesn't sugarcoat the grit. They’re the underdogs now. No more mahogany-row luxury. Instead, we see Peggy Olson and Joey arguing in a tiny room that looks like a closet. Creative is stressed. Pete Campbell is losing his mind trying to keep the lights on.
One of the most authentic things about this season is the depiction of Lucky Strike. They are the "gorilla" in the room. Lee Garner Jr. is a bully, and Roger Sterling is his puppet. When Lee decides to pull the account, it’s a death sentence. It shows the fragility of the 1960s advertising world. You can have the best ideas in the world, but if the guy with the checkbook wakes up on the wrong side of the bed, you’re finished.
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Don's "The Letter" is the turning point. He takes out a full-page ad in the New York Times titled "Why I’m Quitting Tobacco." It’s a desperate, brilliant, and totally selfish move. He frames it as a moral stance, but we all know it’s because he got dumped first. It’s the ultimate Draper move: turning a rejection into a manifesto.
Peggy and Don: The Heart of "The Suitcase"
You can’t talk about this season without talking about "The Suitcase." It’s widely considered one of the best episodes in the history of television. Period. Honestly, it’s basically a two-person play.
The premise is simple: Don makes Peggy stay late to work on a Samsonite pitch on her birthday. They fight. They drink. They talk about things they’ve never told anyone else. Peggy finally confronts him about not giving her credit for the Glo-Coat ad. Don barks back with that famous line: "That’s what the money is for!"
But underneath the shouting, there’s a deep, platonic love. They are the only two people who truly understand each other. Don is grieving Anna Draper—the only woman who ever really knew Dick Whitman—and Peggy is the only person left who can see him clearly. When he finally breaks down and cries in front of her, the power dynamic shifts forever. She’s not just his protégé anymore; she’s his equal. It’s a masterclass in writing. No explosions, no massive plot twists, just two people in a room being honest for once.
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The Problem with Dr. Faye Miller and the Megan Twist
Let's be real: Don should have ended up with Dr. Faye Miller. She was smart, independent, and she actually challenged him. She was a professional who understood the psychology of advertising better than he did. But Don is a broken man, and broken men often choose the path of least resistance.
Faye represented the truth. She told him he’d have to actually deal with his past if he wanted a future.
Then there’s Megan Calvet.
The finale, "Tomorrowland," still feels like a gut punch. After a season of "growth" and soul-searching, Don takes a trip to California with his kids and his secretary. Megan is great with the kids. She’s young, she’s optimistic, and she doesn't know where the bodies are buried. She’s the "fresh start" Don is addicted to. When he proposes to her out of nowhere, it’s a sign that he hasn't learned a single thing. He didn't want a partner; he wanted a bandage.
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Why the Details Matter
The historical backdrop of 1964 and 1965 is woven into the fabric of the show without being "History Channel" about it. You see the subtle shifts in fashion—the skirts getting shorter, the hair getting bigger. The music is changing too. The Beatles are everywhere, and the older generation at the agency looks increasingly confused by it.
- The Honda Pitch: Seeing the agency scramble to land a Japanese account while World War II veterans like Roger and Bert Cooper deal with their lingering resentment is incredibly nuanced.
- Sally Draper’s Rebellion: Kiernan Shipka's performance this season is top-tier. Watching her deal with Betty’s coldness and Don’s absence is heartbreaking. The scene where she runs away to the city and falls in the hallway? It’s a reminder that the kids are the ones paying for their parents' "freedom."
- The Portfolio: Peggy hiring Stan Rizzo is a great bit of office politics. Stan starts as a chauvinist jerk, but he’s actually talented, and their rivalry-turned-friendship is one of the best long-term arcs in the show.
How to Watch Season 4 Like an Expert
If you're revisiting Mad Men Season 4, or watching it for the first time, don't just look at the clothes. Look at the mirrors. Throughout the season, Don is constantly looking at his reflection and not liking what he sees.
Pay attention to the color palette. Notice how the SCDP offices are bright and white compared to the old, wood-paneled Sterling Cooper. It’s supposed to look modern and hopeful, but it also feels clinical and exposed. There’s nowhere to hide in the new office.
- Watch "The Suitcase" twice. Once for the dialogue, and once for the silent acting between Jon Hamm and Elisabeth Moss.
- Track Don’s alcohol consumption. It peaks in this season. The episode "Waldorf Stories" shows him winning a Clio award while being so drunk he loses an entire weekend. It’s a terrifying look at high-functioning alcoholism.
- Contrast Faye and Megan. Look at the advice they give him. Faye tells him he needs to change; Megan tells him he’s already great. It explains every bad decision he makes in the following years.
This season is the peak of the series because it’s the most honest. It’s about the struggle to reinvent yourself when you’re carrying a heavy suitcase full of secrets. It proves that you can change your name, your job, and your wife, but you’re still the same person when the lights go out.
To really get the most out of this era of the show, compare the "Lucky Strike" crisis in the pilot to the "Lucky Strike" departure in Season 4. In the pilot, they save the day with a clever slogan ("It's Toasted"). By Season 4, clever slogans aren't enough to save a dying industry or a dying man. That’s the brilliance of the writing—it shows that the world is moving faster than Don Draper can run.