“Mad Men” is a series that makes masterpieces out of 45-minute chunks. It certainly seeks to tell season-long stories, like the long story of Sylvia’s affair with Don throughout season six, and it can spin gold out of multi-episode arcs, like the one at the end of season five. But what’s essential about “Mad Men” are the moments: Anna Draper’s ghost holding a suitcase, Betty aiming Bobby’s BB gun at the neighbor’s pigeons, Peggy making a power-walking glamorous entrance to her new job at McCann-Erickson. And showrunner Matthew Weiner, along with the rest of the crew behind “Mad Men,” makes those moments indelible by taking great care to frame them into episodes that maximize their impact.
No one is going to agree with my top ten—nor should they. “Mad Men” is beloved—and we can probably all agree that “The Suitcase” is one of its finest episodes—but because the show is so intimate and varied, the moments that hit me hardest are not the ones that will have hit you hardest. But in the spirit of saying goodbye to the show, I wanted to share the episodes that struck a chord with me, the ones that I will think about when I look back on the show—both for their incredible artistry and their emotional impact. I had to leave so many of my favorites on the chopping block. And of course, there’s one episode left that I haven’t had a chance to rank yet. Who knows? It could travel all the way to the top spot.
10. “The Other Woman,” season five, episode 11
Joan has always been one of the show’s most astonishing finds, a character who would be easily dismissed as the token bombshell—and, indeed, most of the characters in the show dismiss her as little more than a hot body. For a long time, that’s all Joan saw for herself, too; the story of “Mad Men” is in part the story of how Joan comes to terms with being a real human, not just a beautiful and desirable woman. “The Other Woman” painfully takes her narrative and turns it on its head: After years of disappointments, both at work and at home, that both assume she’s not capable of business, she accepts a deal with the devil. In exchange for money and partnership, she’ll sleep with Herb, the smarmy Jaguar rep who made the bold and disgusting move of asking for a night with Joan in exchange for the ad deal with Sterling Cooper Draper Pryce. It’s a horrifying prospect, and yet though the viewer can disagree with Joan’s choice, it’s impossible to ignore how unsubtly nearly everyone in her life is pushing her to this high-class whoredom. She’s offered up by her former paramours, Pete Campbell and Roger Sterling; she’s offered up by years of being told she’s nothing more than her body. But in Joan’s hands, it becomes a moment of empowerment. “The Other Woman” also dives deep into Joan’s relationship with Don, who is the only partner who objects on principle; when he shows up to her apartment to prevent her from doing it, her face is a transfixed mask. The deed is already done, and he just doesn’t know it.
9. “Man With A Plan,” season six, episode seven
This is one few others will have on their best-of lists, but when I think about season six, my mind almost immediately goes to this uncomfortable, psychological episode, which examines the nature of Sylvia (guest-star Linda Cardellini) and Don’s season-long affair with each other. In this episode, Don checks her into a hotel and—without asking—starts enacting his own sexual fantasy, asking her to wait for him naked in bed while he goes to work. It’s a consuming kind of adoration, and though Don’s occasionally engaged in sexy power dynamics before, it’s rarely been with this level of detail. Don’s desperate need for control, validation, and all-consuming pleasure matches nicely with Sylvia’s terror about the future and her sense of being trapped in her own life. Don buys her a dress, orders her to crawl on all fours, and even relieves her of her book, curtailing completely the amount of autonomy she has. It ultimately ends up being too much for Sylvia, who has to accept taking responsibility for her own life. The episode is striking for how little Don seems to get that the fantasy can’t last forever. I also particularly like it as a fable that counsels against taking women’s books away from them.
8. “In Care Of,” season six, episode 13
This season-six finale features one of my favorite “Mad Men” devices, which is the Don Draper too-emotional, nearly delirious product pitch—with a twist: It goes horribly awry. Time and time again, Don pulls a pitch out of nowhere, and when he’s selling, the audience—both his clients and the viewers at home—can see that he is purely in his element. His delivery is somewhere between a sermon and spoken-word poetry, and it comes out of something that is purely and solidly felt, which is why it affects his audience so powerfully. “In Care Of” features the pitch where Don Draper jumps the shark—he gets carried away with his honesty, and gets too honest. It’s a heartbreaking denouement, partly because even as we can see Don failing, we can see how desperately he needs to tell the truth this one time. He’s finally acknowledging his own life, and coming to terms with his own crappy secrets; but he’s built a world where he can’t say them out loud. Until now. The episode culminates in a moment of canny reckoning, as Don finally opens up to the person who matters most: his oldest daughter, Sally. He shows her the house where he grew up. She turns to him and gives him a slightly skeptical, slightly impressed look, seeing him as he really is for perhaps the first time.
7. “Waterloo,” season seven, episode eight
Season seven is so fresh in my mind that it’s hard to get a clear view of it, tempered by the distance of a few years. But “Waterloo” is a crazy wonderful episode of “Mad Men,” one engages heavily in putting aside the past and opening up to the future. It’s the last episode of “Mad Men” that takes place in the 1960s, and in perfect homage to the decade, it pivots around the moon landing in July 1969. But what is really happening, in the lives of our characters, is that Sterling Cooper & Partners is on location in Indianapolis, about to make a pitch to BurgerChef. Peggy’s taking the pitch, and she’s nervous. But the moment is a transformative one for everyone—especially, sadly, for Bert Cooper, who watches the moon landing from his home in Florida and dies just hours later. It’s an episode laden with thoughts of death and fear about the future—Ted Chaough half-jokingly threatens to take down Sunkist’s executives in his plane—but for once, it turns on Peggy’s pitch, not Don’s. The woman who, the night before, said in panic: “I have to talk to people who just touched the face of God about hamburgers!” delivers the beautiful line: “You’re starving, and not just for dinner.” Plus Harry Crane getting screwed, and the ghost of Bert singing and dancing to “The Best Things In Life Are Free.” It’s one for the history books.
6. “Smoke Gets In Your Eyes,” season one, episode one
I would be remiss if I didn’t give a shout-out to the pilot of “Mad Men,” an impeccably structured introduction to the world of Don Draper. I keenly remember realizing that Don had a wife and a family upstate, after we’d seen him sleep with Midge (Rosemarie DeWitt) and work alone all day in Manhattan. I have a lot of respect for well-structured beginnings, and “Smoke Gets In Your Eyes” strikes me as one of the most solid: An introduction to the soullessness of advertising and the duplicity of Don Draper, but couched in a way that offers enormous humanity to both flawed creatures. It also squarely sets the stage for the first season, which to my mind is still the strongest 13 episodes of “Mad Men” (although the fifth really does give it a run for its money).
5. “Shut The Door. Have A Seat.,” Season three, episode 13
Unlike most of the third season, “Shut The Door. Have A Seat.” is purely thrilling, an episode that trips from one development to the next so quickly it changes the game four times over. Unlike a lot of plotty episodes, though, every minute of it feels earned. Betty and Don’s marriage finally comes to its inevitable end, with even their divorce scene looking like the picture-perfect model of what Families Ought To Do in their situation. January Jones does some of her best work as brittle, overlooked Betty in this episode, and is shortly thereafter sidelined for the rest of the series, as Don pursues other wives. And meanwhile, the office is in upheaval—the protagonists do some clever wheeling and dealing to secure for themselves an all-new firm, Sterling Cooper Draper Pryce, which requires a lot of shaky partnerships and unlikely alliances. One of “Mad Men”’s strengths throughout its run is how well it made corporate drama seem not just interesting but vital. This episode is one of the best examples. The highlight for me is when Don apologizes to Peggy for making her feel unimportant, and then tells her that she understands what he does: That people leave something of themselves behind when they start buying things for money. She cries, because she, like Don, has left a great deal behind.
4. “The Wheel,” season one, episode 13
“The Wheel” is the precursor to “In Care Of,” and in some ways, it’s even more devastating. Don’s pitch to Kodak is so affecting that it’s an immediate winner, without all of the sloppiness that comes years later. But it’s also nothing more than a fantasy, and the man who desires that fantasy the most is a man to whom the fantasy is hardest to grasp. Don Draper has spent his life as a lie, trying to be the perfect man, trying to be anything except himself. Along the way, he sacrificed real intimacy with his wife, and anything like contentment with his children. In “The Wheel,” he knows it, for maybe the fist time. It all boils down to that last shot, where he races home only to realize that his family has left for Thanksgiving without him. He vividly imagines his homecoming with them there, excited to see him; in reality, he sits on his stairs, cold and sad, with only his own dreams to keep him company. (Peggy, meanwhile, obtains an intimacy she doesn’t even want, when her child is born almost without her noticing.)
3. “The Hobo Code,” season one, episode eight
This was the first episode to delve seriously into Don’s backstory, as the child Dick Whitman, and given how unfamiliar the territory is, it’s outright heartbreaking. Margaret Lyons wrote about this episode just this week, following the penultimate episode of the series, “The Milk And Honey Route”—that theme of wandering without burdens has returned to the show very strongly in its final hours. What “The Hobo Code” offered up in season one was a glimpse into just how wretchedly Don grew up—and the terrible twist of the knife it is to discover the limitations of your own parents, to see them low, the way other people see them. The revelation of the episode sneaks up without warning, as the episode is caught up in the storytelling of a hobo coming to the Whitman farm to visit and then taking his leave. But as he leaves, without his promised quarter, young Dick runs to the gate. Acting on a hunch, he clears the shrubbery by the post to reveal a hand hooked like a scythe or a claw—the code for “a dishonest man lives here.” It’s a chilling moment of realization, masterfully executed.
2. “The Suitcase,” season four, episode seven
“The Suitcase” is on everyone’s best-of lists—that’s just how good it is. I never quite reconciled with the creative decision to show Anna Draper’s ghost walking through Don’s office, carrying the titular suitcase, but everything leading up to that final scene of grief is kind of incredible. The episode is at the literal midpoint of the show—the seventh episode of a 13 episode season, the fourth season in a seven-season run—and it is the hinge on which the whole show pivots, from “Smoke Gets In Your Eyes” to the as-yet unseen “Person To Person.” It is, therefore, an episode about Don and Peggy, where they seem to meet each other as equals—cranky, workaholic, equals—for the first time since the series started. Intimacy doesn’t come comfortably to either of these people; over one long, grueling night, they fight and reminisce and come to terms, both with themselves and each other. Peggy ditches a date; Don avoids a phone call. Both find solace in the last thing left that provides them meaning, but even that isn’t quite enough. What they really only have is their ability to comfort the other.
1. “Babylon,” season one, episode six
It’s a weird choice, I’ll grant you that. It’s not an obvious contender for brilliance, and it’s not an episode where a whole lot of things happen. But “Babylon” is when I first fell in love with “Mad Men,” and I’ve revisited it and loved it since. Seven of the nine writers on “Mad Men” are women, and episodes like “Babylon,” which is infused with attention and care to feminine conditioning, are when that perspective really wins out. This is the episode where Peggy first gets the chance to start writing copy, when the women in the office try out an array of Belle Jolie lipsticks and she tells Freddy Rumsen that women don’t want to be just one color in a box, even if the discarded lipstick tissues are a basket of kisses. Later in the episode, Betty applies lipstick on Sally for the first time. Joan, the only woman who knows that the mirror in their testing room is really a window, puts on a little show for the men watching, putting on her lipstick with carefully measured eroticism. Don, meanwhile, seeks out Rachel Menken—his greatest love—to talk to her about a tourism campaign for Israel, ostensibly, but really just to see her again. He asks her why Israel matters. She says it’s a home, even if she’s never been there. And it’s a deeply romantic moment for them both—a moment of shared longing—because wherever or whatever Don’s home is, he’s not there, either. Instead they both are in Babylon—exile in a strange, multilingual city, looking for somewhere to belong.
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