Don Draper is coughing. It’s a wet, hacky, morning-after-the-stoli-bottle cough that vibrates through the empty walls of his sad little Greenwich Village apartment on Waverly Place. If you watched the first three years of the show, you were used to the glamour of the Ossining house and the blue-hued perfection of Betty Draper’s kitchen. But Mad Men Season Four changed everything. It felt like a cold shower. Or maybe a slap in the face from someone you actually respected.
Most shows, when they hit their fourth year, start to get comfortable. They lean into the tropes that made them famous. But Matthew Weiner decided to blow up the entire foundation of the series. He burned down the old agency, ended the marriage, and forced us to look at Don Draper not as a suave ad man, but as a desperate, lonely guy who was rapidly losing his grip on the world. Honestly, it was a gutsy move.
The Year of the "Who Am I?" Crisis
The season kicks off with a reporter asking Don a simple question: "Who is Don Draper?"
He can’t answer it.
The fourth season, which aired back in 2010, takes place between November 1964 and October 1965. This isn't just a backdrop; it’s a character. The world is getting louder, weirder, and much more cynical. The shiny, optimistic JFK era is dead. Instead, we get the gritty, soot-covered reality of a startup—Sterling Cooper Draper Pryce—operating out of two floors in the Time-Life Building. It’s cramped. It’s messy. People are literally working on top of each other.
You’ve got Roger Sterling trying to keep his relevance while writing a memoir nobody wants to read called Sterling’s Gold. You’ve got Peggy Olson finally finding her voice, even if it means clashing with the man who gave her a career. This is where the power dynamics shifted permanently.
The Suitcase: Why Episode Seven Still Matters
If you ask any TV critic worth their salt—someone like Alan Sepinwall or Matt Zoller Seitz—they’ll point to "The Suitcase" as the high-water mark of the entire series. It’s basically a two-person play. Don and Peggy stay up all night working on a Samsonite pitch, but it’s really about their souls.
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Don is grieving the death of Anna Draper, the only person who actually knew his secret identity as Dick Whitman. Peggy is grieving the fact that her birthday is being ignored and her boyfriend is a dud. They yell. They drink. They watch Cassius Clay fight Sonny Liston on the radio. Don cries. It’s one of the few times we see him truly vulnerable, stripped of the suit and the ego.
When people talk about Mad Men Season Four, they’re usually talking about the intimacy of this specific episode. It proved that you don't need a huge cast or a complex plot to make great television. You just need two people in a room being honest for the first time in their lives.
The New Women of 1965
The casting in this season was perfect. We were introduced to Faye Miller, played by Cara Buono. Faye was a consumer researcher—a professional woman who was actually Don's intellectual equal. She didn't need him to provide for her. She challenged him.
And then, of course, there’s Megan Calvet.
The finale, "Tomorrowland," is still a point of contention for fans. Don goes to California, realizes he’s miserable, and instead of choosing the woman who actually understands him (Faye), he proposes to his secretary (Megan) because she’s good with his kids and represents a "fresh start" that he hasn't earned. It’s a classic Don Draper move. It’s impulsive, it’s self-destructive, and it’s deeply human. He’s running away from the work of being a better person.
- Peggy Olson: No longer just a "girl" in the office. She’s a creative force who buys her own apartment and starts hanging out with the Warhol crowd.
- Joan Harris: Dealing with a husband in Vietnam and an unplanned pregnancy with Roger. Her stoicism this season is heartbreaking.
- Sally Draper: Kiernan Shipka’s performance in season four is where she became a star. Her struggle with Betty—culminating in the scene where she cuts her own hair—is the most realistic depiction of 1960s adolescence ever put on film.
The Business of Being Small
In the earlier seasons, Sterling Cooper was a legacy firm. They had the luxury of being arrogant. In the fourth season, they are the underdogs. They are "scrappy."
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Watching them try to land Honda or losing Lucky Strike (the account that made up roughly 70% of their billings) felt like a high-stakes thriller. When Lee Garner Jr. fires the agency, the panic is palpable. We see the real cost of Don’s "The Letter" in the New York Times—where he famously dumps the tobacco industry before they can dump him. It was a PR masterstroke, but a financial disaster.
The show did something brilliant here: it used the business side to mirror Don’s internal collapse. As the agency lost its luster, Don lost his. He was drinking more, coughing more, and waking up with women whose names he barely remembered. The "Summer of Don" was actually a downward spiral into a dark, boozy abyss.
Historical Touchstones That Actually Influenced the Plot
- The Civil Rights Movement: We see it in the background of the New York streets and in the hiring (or lack thereof) at the agency.
- The Death of Anna Draper: This removed Don's last link to his "real" self, forcing him to either evolve or double down on his lies.
- The Rise of Consumer Psychology: Dr. Faye Miller represents the shift from "intuition-based" advertising to data-driven insights.
Why We Still Revisit This Season
Honestly, a lot of shows from that era haven't aged well. But Mad Men Season Four feels more relevant now than it did in 2010. We live in a world obsessed with personal branding and "restarts." We see people on Instagram pretending their lives are perfect while they’re falling apart behind the scenes. Don Draper was the original influencer, except his "feed" was a 30-second spot for Coca-Cola or a full-page ad in the Times.
The season doesn't give us a happy ending. It gives us a complicated one. When Don proposes to Megan, it’s not a romantic triumph. It’s a tragedy. We know he’s making the same mistake he made with Betty. We know he hasn't changed.
The craftsmanship is just... it's on another level. The costume design by Janie Bryant shifted from the structured New Look of the late 50s to the shorter hems and bolder patterns of the mid-60s. The cinematography became tighter, more claustrophobic. Even the sound design—the constant hum of the city and the clack of typewriters—felt more aggressive.
Actionable Takeaways for the Mad Men Superfan
If you're planning a rewatch or just diving into the lore for the first time, keep these specific things in mind to get the most out of the experience.
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Watch the background characters. Season four is when the "support staff" starts to have lives. Stan Rizzo, the art director, is introduced here. He’s the bearded, cynical foil to Peggy who eventually becomes one of the most important people in her life. Pay attention to how he pushes her.
Analyze the "Don's Journal" voiceover. In the episode "Summer Man," we get a rare glimpse into Don's internal thoughts via his diary. It’s the only time the show uses this device. It’s a fascinating look at a man trying to use "discipline" to fix a broken soul. It never works, but the attempt is revealing.
Focus on the children. Sally and Bobby are no longer props. They are victims of their parents' divorce. The scene where Sally runs away to the city to see Don is a turning point for the series. It forces Don to realize he can't just be "the guy who visits on weekends." He has to be a father, even when it’s inconvenient.
Track the booze. The drinking in season four is different. It’s not celebratory. It’s medicinal. Notice how many scenes involve Don drinking alone in the dark compared to previous seasons. It’s a subtle but powerful way the directors showed his isolation.
If you want to understand why this show is considered a masterpiece, go back and watch "The Suitcase" tonight. Don't look at your phone. Don't multi-task. Just watch two people realize that they are the only ones who truly see each other. That’s the heart of the season. It’s messy, it’s loud, it’s sometimes uncomfortable, but it’s undeniably real.
To dive deeper into the historical context, look up the real-life 1964 New York World's Fair. The show uses the "Future" promised by the fair as a sharp contrast to the crumbling reality of its characters' lives. It’s that irony that makes the season stick in your brain long after the credits roll.