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Pop culture obsessives writing for the pop culture obsessed.

10 episodes that show the best of Mad Men’s many facets

Illustration for article titled 10 episodes that show the best of Mad Men’s many facets

With so many new series popping up on streaming services and DVD every day, it gets harder and harder to keep up with new shows, much less the all-time classics. With TV Club 10, we point you toward the 10 episodes that best represent a TV series, classic or modern. If you watch these 10, you’ll have a better idea of what that series was about, without having to watch the whole thing. These are not meant to be the 10 best episodes, but rather the 10 most representative episodes.

Of all of the series on TV, none is so acclaimed as Mad Men, AMC’s cool, analytical depiction of the emotional turmoil running through the hearts and minds of the men and women who work at a ’60s ad agency. The winner of four Emmys for Best Drama Series (a record matched only by Hill Street Blues, L.A. Law, and The West Wing) and quite easily one of the best reviewed series of the past 10 years, Mad Men can seem an almost unapproachable monolith. The show has a reputation for being smart TV but also for being slightly aloof TV. It holds viewers at arm’s length, almost daring them to get involved.

Where other great TV dramas—Breaking Bad, say, or Justified—are visceral, pumped full of thrills and plot that make the vegetables of character and thematic depth go down a little more easily, Mad Men is more like a series of interlocking character studies. To understand why requires going back to the series Mad Men creator Matthew Weiner worked on immediately before his current show: The Sopranos. If there’s any series on TV that carries on that show’s mantle of complex, rewarding storytelling that’s nonetheless a little symbolically opaque and thematically impenetrable, it’s Mad Men. And like that earlier series, Mad Men is structured less as a straightforward, novelistic arc than as a series of short stories based on the same characters.


Where other shows attack the character arc as a linear progression, both Mad Men and The Sopranos consider it a thing that happens in dribs and drabs. People don’t change, until they abruptly decide to, then just as abruptly decide to reverse it. A storyline may seem to have ended until it abruptly resurrects itself. Characters may retreat to mostly supporting roles for long stretches of the season, then abruptly be revealed as hugely important to whatever story happens to be most pressing at that moment. In addition to these other similarities, Mad Men has a similarly inventive tone to its filmmaking. It uses the gorgeousness of its production design as an asset, and is filled with shots that lay out the characters’ relationships and power dynamics with a pleasing simplicity that nonetheless has incredible levels of depth.

All of that makes the show seem like homework, and indeed, it can take a bit—perhaps as long as the whole first season—to figure out what the show is up to. Unlike many of its dramatic cousins, Mad Men is less interested in narrative momentum than it is in character accumulation. Events that happen across the years build upon each other, until minor declarations in the show’s fifth season feel like they have momentous weight behind them. Like other shows that have relied on this storytelling approach, this can make each season feel better than the last, and a significant number of fans will argue for the show’s latest season as its best, even as it’s airing.

Yet the series isn’t just the austere elements that have driven so much of its acclaim. It also has a significant number of pleasures. For one thing, it’s frequently among the funniest shows on TV, with all of its characters capable of abrupt, lacerating wit. Weiner and his writers don’t use plot to excess, but when an incident disrupts the calm of the advertising office, it’s almost always out of left field, as in a devastating accident that befalls the office in a season-three episode (and provides a visual rhyme for the Kennedy assassination, whose imminence dominated that season).

Also, the show’s characters are perhaps the deepest bench of strongly developed characters on all of television. Yes, the main character, Jon Hamm’s Don Draper, is one of TV history’s most fascinating figures, a poker-faced charlatan who’s somebody different for everyone he meets, yet boasts a core of wrenching sadness. But the rest of the series is filled out with fascinating figures, some of whom have disappeared over the years and some of whom have unexpectedly become major characters. When the show hands a significant portion of an episode’s running time to, say, TV department head Harry Crane (Rich Sommer), that storyline can be as moving and profound as anything Don gets up to.


Paradoxically, all of this makes sampling the show’s pleasures easier for those who are willing to dig a little. Granted, as with most serialized drama of the post-Sopranos era, watching Mad Men straight through is the best choice, but it also seems to stymie a surprising number of viewers, who simply can’t get used to the character-accumulation model and ditch the show somewhere in the first two seasons. But potential viewers willing to skip around in the series a bit—and perhaps read an online guide to figure out what’s been missed between episodes—will see the show’s short-story model at its best and observe how the series uses that model to turn individual episodes into what are almost character vignettes. While hopping around through the series might seem counterintuitive, it can work, both for the newbie and for the veteran who just wants to revisit series’ highlights before the upcoming première. And don’t worry about spoilers: Mad Men’s plot details are rarely as important as how characters react to them in the moment. Knowing that something is coming rarely destroys that moment.

With that, here are 10 episodes that show off 10 vital characters and aspects of Mad Men:

Don Draper, “The Gypsy And The Hobo” (season three, episode 11): By far the most important figure on Mad Men, Don Draper is a coolly analytical man who does his best to not let the past haunt him. He’s a shark, cutting his way through the mess of the ’60s, and he’s blithely unapologetic about this. Yet Don is harboring a deep secret, one he lets few in on, and it’s a secret that splits him into several different men, depending on whom he’s talking to. (For instance, in this episode, he’s a slightly different man with a mistress than he is with his wife.) In “The Gypsy And The Hobo,” someone learns Don’s secret, and the way he unravels afterward is exquisite, and perhaps the closest the series has ever gotten to the “true” Don Draper.


Peggy Olson, “The New Girl” (season two, episode five): If Don is the face of a world that’s rapidly slipping into the past, then Peggy is the new world that’s being born right before the characters’ eyes, even if she’d never think of herself as such (or want to be perceived as such). Played by Elisabeth Moss, Peggy becomes Don’s most important student as the series goes on, and she exemplifies the way the show’s true core is about relations between the genders, both in the ’60s and, by extension, right now. In “The New Girl,” Mad Men dips back into the past to fill in some crucial information about something that happened to Peggy, but it also features an interloper in Peggy’s apartment, trying to figure out just who this woman is. Trying to crack the code of who other people are and what they want is as central to this show as it is to advertising itself.

Pete Campbell, “Signal 30” (season five, episode five): One of the sneakily genius things about Mad Men is how over the course of the series—which runs from 1960-1967 as of the end of season five—the various men in the cast age up into new versions of their characters. Vincent Kartheiser’s Pete Campbell started Mad Men as a junior-league weasel, constantly butting his head against others at the agency and pushing for more and more responsibilities. The thing is, Pete is often right about coming movements that will greatly affect the advertising industry, even if people are loath to listen to him. In “Signal 30,” the series delves deeper into Pete’s loneliness and loathsomeness than ever before, setting up a season that wounded him, even as he was completely oblivious to it much of the time.


Betty Draper, “Shoot” (season one, episode nine): Mad Men never wanted to be just a series about its office setting or even its time period. It also wanted to chronicle the many marriages of those who worked at the office and how they fell apart, evolved, and drifted. The most important spouse when the series began was January Jones’ Betty Draper, and for as vilified as the character has become by fans of the show (often for understandable reasons), she was a genuinely sympathetic and fascinating figure in the early going, a childlike woman who found herself married to exactly the wrong man. “Shoot” is a great reminder of how vital Betty seemed to the show at that point in time, and of what colors she brings to its worldview.

Joan Holloway, “A Night To Remember” (season two, episode eight): Mad Men may have the word “men” in its title, but it’s become almost better known for its female characters, particularly its central trio of Peggy, Betty, and Joan. Joan, played by Christina Hendricks, begins the series as the queen secretarial bee of the office, but as the series wears on and women begin to enter the workplace, that role holds less and less pleasure for her. This season-two episode depicts one of her first ventures into other sides of the business, as she delves into the world of TV ad sales with Harry, a man who’s making up the department as he goes. As a bonus, the episode works as a terrific way to introduce viewers to further information about Betty and Peggy.


Roger Sterling, “Red In The Face” (season one, episode seven): Mad Men isn’t afraid to take its time, and then reveal its long game all in an instant. It’s this quality that makes the show a rough sit for some viewers, but once it has its hooks in, it rarely lets go. This might be why it’s better to save this famous season-one hour, with its long, languid dinner-table scene filled with subtext, for slightly later in a prospective introduction to the show. It also works as a great introduction to Roger Sterling, Don’s superior and best friend, as well as the man Don will one day become. As played by John Slattery, Roger’s the great wit of the show, but his wit masks something indefinable and sad at the character’s core.

Sally Draper, “The Beautiful Girls” (season four, episode nine): Mad Men hit the jackpot when it cast a young Kiernan Shipka as Don’s oldest child, the strangely wise, always wounded Sally Draper, a young girl who seems to be drinking in everything around her and saving it up for the intense therapy she’ll need in 1985. In season three, the series tentatively started giving Sally actual storylines, and when Shipka proved up to the task, seasons four and five offered even more, to the point where it started to seem like Sally might be the series’ stealth protagonist. “The Beautiful Girls” is a great example of what makes Sally so fascinating, as she runs away from home to join her father at his office and finds herself passed between many women who could represent her future.


The advertising office, “Shut The Door. Have A Seat” (season three, episode 13): Technically, there are several different advertising agencies depicted throughout the run of Mad Men, with two of them serving as major settings for the series. To say more would be to spoil the sheer delight of this episode, the third-season finale and one of the best episodes of Mad Men ever produced. What’s great about “Shut The Door” is that it outlines the dynamics of the many people who work in the office, even as its main plot plays out in a way that will be highly entertaining to the uninitiated, yet more rewarding for those who know the show’s setting and characters. “Shut The Door” doesn’t just capture how well Mad Men does office politics; it captures how fun the show can be and offers a terrific capper to the show’s most uneven season.

Mad Men’s experimental bent, “Far Away Places” (season five, episode six): Like The Sopranos, Mad Men has an occasional inclination toward the experimental, offering up episodes that tell stories through dream sequences or odd visuals or even—as in this episode—drug trips. But “Far Away Places” has elements of experimentation that extend beyond the drug sequence, including a tripartite structure that splits the episode into three different pieces, following three different characters through the same day. In addition, it will function as an excellent consideration of Megan (Jessica Paré), whose character is incredibly important to the series’ fifth season.


The Don and Peggy relationship, “The Suitcase” (season four, episode seven): Mad Men often uses its seventh episode—each season’s midpoint—as a kind of break in the action, with characters pausing in whatever’s happening in the season up to that point to have moments of personal connection or growth. There’s no better example of this than “The Suitcase,” another of the best Mad Men episodes ever and one that zeroes in on the show’s central relationship, the friendship/mentorship between Don and Peggy, which is remarkable for just how much respect and value each character has for the other. In “The Suitcase,” the two spend a long night in the office, starting from a place where their relationship seems to be falling apart. In its literate, melancholy beauty, “The Suitcase” reveals how deeply moving Mad Men can be, even when there doesn’t seem to be all that much happening on the surface.

And if you like those, here are 10 more: Don Draper: “The Wheel” (season one, episode 13); Peggy Olson: Three Sundays” (season two, episode four); Pete Campbell: Flight 1” (season two, episode two); Betty Draper: The Chrysanthemum And The Sword” (season four, episode five); Joan Holloway: Guy Walks Into An Advertising Agency” (season three, episode six); Roger Sterling: “Long Weekend” (season one, episode 10); Sally Draper: At The Codfish Ball” (season five, episode seven); the advertising office: Lady Lazarus” (season five, episode eight); the show’s experimental bent: The Jet Set” (season two, episode 11); the Don and Peggy relationship: The Other Woman” (season five, episode 11).


Availability: The complete run of the series is available on DVD and Blu-ray. It’s also available on Netflix Instant, as well as on Amazon and iTunes for paid download.

Next time: Todd VanDerWerff goes where everybody knows your name and boils down more than 200 episodes of Cheers to just 10 must-sees.


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