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The Top 20 Episodes of ‘Mad Men’

The Top 20 Episodes of 'Mad Men'

AMC is rolling out the red carpet for the end of an era. As Entertainment Weekly reported yesterday, AMC’s partner networks (BBC America, IFC, Sundance, and WE) will blackout regular programming while the highly anticipated “Mad Men” finale airs Sunday, and AMC will run a marathon of all 92 episodes to date beginning tonight at 6pm. Gird yourself: the network’s nostalgic promo is already an emotional roller coaster, and it’s only a minute long.

READ MORE: “Watch: The Final ‘Mad Men’ Promo Will Have You in Tears”   

When I first published a version of this guide to the series’ finest hours last spring, before the premiere of the seventh season’s first half, I knew my top ten list would soon be out of date. The 13 episodes since (and yet another re-watch of the entire series) have made clear that it’s high time for a revised, expanded version. So whether you’re ready to gorge yourself before it’s gone or simply want to revisit a few of its many classics, here’s your guide to the top 20 episodes of “Mad Men.”

READ MORE: “7 Things to Learn from ‘Mad Men’ Creator Matthew Weiner About Compelling Storytelling (EXCLUSIVE VIDEO)”

20. “The Grown Ups,” Season 3 (Episode 12)
For a series so committed to showing us the quotidian details of the 1960s as history’s residents lived it, “Mad Men” has not always been graceful in its treatment of the era’s political and social upheaval—particularly when it’s come to racism, race relations, and the Civil Rights Movement. “The Grown Ups,” however, interspersed with archival footage of newsmen and ordinary Americans desperate to process the assassination of John F. Kennedy, weaves a potent portrait of collective grief. “The flash, apparently official,” comes as the phones of Sterling Cooper go suddenly silent, on the eve of Margaret Sterling’s (Elizabeth Rice) disastrous wedding, and the way each character integrates the chaos into their preexisting notions of how the world works is rendered in precise, efficient strokes. “It felt for a second like everything was about to change,” Pete Campbell (Vincent Kartheiser) tells his wife, Trudy (Alison Brie), referring as much to his own reversals of fortune as to those of the country, but it’s Joan Harris (Christina Hendricks) whose words echo the main themes of “Mad Men” most strongly. “People are still getting sick, car accidents are happening, babies are being born,” she tells Roger Sterling (John Slattery), understanding that even in tragedy time presses forward, relentless.

19. “The Better Half,” Season 6 (Episode 9)
Of the sixth season, often considered the series’ weakest, the rudimentary excitements of “The Better Half” might not seem an obvious choice for this list. But the sight of Peggy Olson (Elisabeth Moss), anxious about a spate of
recent neighborhood crimes, accidentally stabbing her boyfriend, Abe
(Charlie Hofheimer), in the middle of the night, or of the enigmatic
Bob Benson (James Wolk) wearing short shorts printed with palm trees, are alone enough to qualify. Yet
the heart of the episode is Betty Draper Francis’ (January Jones) rousing comeback. Her
one-night dalliance with Don (Jon Hamm) represents a powerful reversal: while she
revels in the pleasure of sex and the ease of pretending it never
happened, Don watches her wistfully, still hoping to write a different
ending. “I love the way you look at me when you’re like this, but then I
watch it decay,” she says frankly. “I can only hold your attention so
long.”

18. “Lost Horizon,” Season 7 (Episode 12)
As advertising behemoth McCann Erickson absorbs Sterling Cooper & Partners, and with it Don’s desire, as he once told Bert Cooper (Robert Morse), “to build something,” “Mad Men” turns toward home with a profound sense of dreams deferred. Don, yearning for freedom as he stares at a plane’s faint contrails, lights out for the territory once again, ever the Huckleberry Finn of series creator Matthew Weiner’s fertile imagination; Joan challenges sexism at work only to find herself stymied; and Roger, playing a ghostly tune in SC&P’s abandoned offices, mourns all the lives he didn’t live. The defining image of “Lost Horizon” is of Peggy, strutting into McCann with sunglasses on her face, a cigarette hanging from her lips, and a salacious work of art under her arm, but as its title suggests, the episode is run through with disappointment. Chasing the horizon is a fool’s errand—it will never be caught—but it’s those who stop trying that seem, at the end of this strange, gorgeous hour, most bereft.

17. “Tomorrowland,” Season 4 (Episode 13)
The strength of the season four finale rests on a handful of fraught exchanges, sutured together by phone calls, closed-door meetings, and cannonballs in the pool. Each of these turns on the mixture of the personal and the financial that so often destabilizes “Mad Men.” If Betty’s casually racist remarks in firing Carla (Deborah Lacey) point to the emerging cruelty of a woman who’s outsourced motherhood, Megan (Jessica Paré) and Don’s Disneyland liaison reveals that the caregiver’s touch is worth more to him than a salary. Perhaps the most satisfying scene in “Mad Men” history arrives along these lines: Peggy, the overlooked copywriter who just brought in new business, and Joan, the underappreciated office manager who ensures the business runs in the first place, commiserate about this gulf between what we pay for and what we value. “That’s bullshit,” Peggy snipes, and the chuckle they share in that moment registers as a kind of rebellion.

16. “Smoke Gets in Your Eyes,” Season 1 (Episode 1)
“Advertising is based on one thing,” Don tells the executives of American Tobacco midway through the series’ pilot. “Happiness.” The first hour of “Mad Men” is as deceptively simple as its protagonist’s pitch, following Don as he romances Midge (Rosemarie DeWitt), a bohemian Village artist, spars with department store heiress Rachel Mencken (Maggie Siff), and rejects a clumsy pass from Peggy. “Smoke Gets In Your Eyes” sits squarely on Don’s shoulders, but its liveliness derives from the array of complex women he encounters, much like the series as a whole. (“You know the rules,” Midge reminds him. “I don’t make plans, and I don’t make breakfast.”) By the revelatory final moments—a Norman Rockwell-esque image of Don at his children’s bedside, Betty framed in the door behind him—“Mad Men” firmly establishes the difference between selling the dream and trying to live it.

15. “Seven Twenty Three,” Season 3 (Episode 7)
“Seven Twenty Three,” set, we learn in its final scene, on July 23, 1963, opens with three striking images, separated by hard cuts to black: Peggy in bed with an unknown man, Betty reclining on a Victorian fainting couch, Don sprawled on his face on the motel-room floor, a bloody gash along the side of his nose. One of several innovative triptychs in the “Mad Men” canon, including “Three Sundays” and “Far Away Places,” the episode subsequently follows each of its protagonists to the moment at which we first see them, evoking torrents of frustrated desire, personal and professional, at every turn. Though unassuming, it establishes the narratives that carry the third season to its rousing conclusion. As Duck Phillips (Mark Moses) courts Peggy for a job at Gray and a little nookie on the side, Betty’s attraction to Henry Francis (Christopher Stanley) deepens during a solar eclipse. The possibility of escape beckons, but for now the characters—including Don, reluctantly signing a contract to please Connie Hilton (Chelcie Ross)—hold back. The way out is never completely closed off, however. As Bert Cooper assures Don, “After all, when it comes down to it, who’s really signing this contract, anyway?”

READ MORE: Why Betty Draper Will Always Be My Favorite “Mad Men” Character

14. “The Jet Set,” Season 2 (Episode 11)
The lure of California frequently turns the dream westward, most forcefully in the mirage-like “The Jet Set.” As Don escapes an aeronautics convention with Joy (Laura Ramsey) and her band of wealthy “nomads,” Los Angeles and Palm Springs enjoy the Chamber of Commerce treatment—sketched in white, turquoise, and sunshine as a theme reminiscent of “South Pacific” dances languidly on the soundtrack. But it’s the episode’s delicate rendering of what prevents us from starting fresh that lends depth to the picture postcard. Duck, a recovering alcoholic, relapses in a dim Italian restaurant; Roger and Peggy repeat the same old romantic mistakes; Sal (Bryan Batt) remembers why the closet door remains shut. Even the chameleonic Don understands that no amount of wealth or distance can erase his past. “Hello, it’s Dick Whitman,” he says over the phone at episode’s end. No matter how far we travel, “The Jet Set” suggests, life has a funny way of sending us back to where we came from.

13. “Babylon,” Season 1 (Episode 6)
Watching this brilliant first-season entry again now, the extraordinary thematic density of “Mad Men” is more clear than ever. As if to set up the terrible news of “The Milk and Honey Route” a decade in advance, Betty describes her late mother as “fetching… to the very end,” while Peggy makes her first strides on the road to becoming copy chief by saying, of Belle Jolie lipstick, “I don’t think anyone wants to be one of 100 colors in a box.” Yet the key sequence in “Babylon” comes as Don asks Rachel for guidance in his pursuit of the Israeli tourism board account. “They taught us at Barnard about that word, ‘utopia,’” she says, laying out the central dilemma of the impossible “American Dream” in the process. “The Greeks had two meanings for it: ‘eu-topos’, meaning ‘the good place,’ and ‘u-topos,’ meaning ‘the place that cannot be.'”

12. “The Milk and Honey Route,” Season 7 (Episode 13)
The impending demise of Betty Francis arrives without warning, even if a life lived with a cigarette in her mouth was bound to catch up with her someday. Though “The Milk and Honey Route” features Don meeting a young con artist much like himself and Pete convincing Trudy to come with him to Kansas, the affective center of the episode is Betty’s startling diagnosis—aggressive, metastatic lung cancer—and the consequences that follow. After years of struggling to find her voice, she’s struck down at the outset of her studies in psychology, and yet she bears up with remarkable grace. Her matter-of-fact letter to Sally, filled with funeral instructions and the humane honesty of a woman with no time left to lie, may be the most heartbreaking sequence in a series that’s never shied away from life’s sorrows, but there’s a kind of hopeful wisdom in it, too. “Sally, I always worried about you because you march to the beat of your
own drum,” she writes, repairing their tumultuous relationship at a stroke. “But now I know that’s good. I know your life will be an adventure. I
love you.”


11. “The Phantom,” Season 5 (Episode 13)
Were it not for the overly insistent conceit of Don’s “hot tooth,” “The Phantom” would earn an even higher place on this list. Coming at the end of the series’ best season, it depicts the rottenness inside the creative director through a series of hauntings. The apparition of Don’s younger brother, Adam (Jay Paulson), who took his own life as a result of Don’s callousness, is matched only by the specter of another, more recent suicide, that of Lane Pryce (Jared Harris). Don tries to make amends, as he did with Adam, by paying off Lane’s wife (Embeth Davidtz), but once again the attempt to absolve his guilt without confessing his sins proves no absolution at all. “Don’t leave here thinking,” she chides him, “that you’ve done anything for anyone but yourself.” By the time the episode comes to a close, with two of the most perfect shots I’ve ever seen on television, the sense of progress—the removal of the tooth, the sight of the five remaining partners arranged in a row on what will be SCDP’s second floor—is undercut by the suggestion that Don’s right back where he started. As in “The Wheel,” he watches his wife fondly (this time it’s Megan’s screen test), but he soon pulls away. The bright, colorful stage where she’ll shoot her first commercial recedes as Don steps into the darkness, ever the phantom, and Nancy Sinatra’s “You Only Live Twice” rises on the soundtrack. “You only live twice,” she half-promises, “or so it seems—one life for yourself, and one for your dreams.”

10. “The Crash,” Season 6 (Episode 8)
Yet another inventive hour that might be higher on this list, were it not for the troubling interlude in which a black woman calling herself “Grandma Ida” tricks the Draper kids into letting her burgle Don’s apartment, “The Crash” is not an episode I much appreciated when it first aired. With repeated viewings, however, it’s become clear that the frantic, amphetamine-fueled weekend at Sterling Cooper Draper Pryce Culter Gleason and Chaough it depicts is less a desperate departure than the culmination of characters so long spinning their wheels. From the tap dancing Ken Cosgrove (Aaron Staton) to the knife in Stan’s (Jay R. Ferguson) arm, the episode overflows with unexpected delights; the sound design—patches of silence abruptly interrupted by the loud bleat of telephones and the hammering of typewriters—is among the series’ best. For all the playful language, however, clanging with allusions, puns, and switchbacks, the uppers in the ass are a metaphor for the illusion of immortality. Even Don’s sage words, describing the importance of style along with substance, or the way history “holds people together,” are ultimately as fleeting as the staff’s burst of energy. In the cold light of day, all that’s left are the compromises made in the name of selling Chevys. “Every time we get a car,” Don tells Ted Chaough (Kevin Rahm) and Jim Cutler (Harry Hamlin), “this place turns into a whorehouse.”

9. “Mystery Date,” Season 5 (Episode 4)
Exceedingly dark and tightly wound, “Mystery Date” frames the war of the sexes as a pitched and bloody battle. Set in the days
following what Peggy’s friend, Joyce (Zosia Mamet), memorably calls “the
student nurse massacree,” the episode is an exemplar of the series’
multifaceted intelligence, weaving four distinct narrative arcs into the
historical backdrop. At the episode’s center is the lurid triumvirate
of sex, violence, and salesmanship, and each thread—Joan drops Greg
(Sam Page); Peggy stands up to Roger; Don encounters an old flame;
Ginzburg (Ben Feldman) pitches an idea—uneasily echoes this theme.
Even the vertiginous camera angles and splashes of garish color (a
single, hot pink shoe) in otherwise placid, drab surrounds feel like the
stranger knocking at the door. Indeed, “Mystery Date” critiques the
titillation industry by highlighting our complicity in it. After all,
it’s Ginzburg—his conscience quailing at the image of “some girl
trussed up like a cut of meat”—who sells this troubling fantasy the
hardest. “She knows she’s not safe, but she doesn’t care,” he says at
the close of his “dark Cinderella” pitch. “I guess we know, in the end,
she wants to be caught.”

8. “Shut the Door. Have a Seat.” Season 3 (Episode 13)
Despite its (undeserved) reputation for desultory pacing, “Mad Men” occasionally
devotes an hour to office machinations, and “Shut the Door. Have a
Seat.” cleverly assumes the staccato rhythm of the title’s declarative
statements. In a deft feat of narrative construction, the formation of
Sterling Cooper Draper Pryce from the ruins of a corporate raid is
fragmented into several negotiations, moving seamlessly from the playful—Lane’s telephone conversation with an irate St. John Powell—to
the poignant—a cathartic interlude with Peggy and Don that sets the
table for “The Suitcase.” “There are people out there who buy things,
people like you and me,” he says. “And something happened. Something
terrible. And the way that they saw themselves is gone.” It’s a moment
built from three seasons of secrets and two lifetimes of grief, no less
thrilling than the rest of the episode for being another kind of
conspiracy entirely.

7. “Far Away Places,” Season 5 (Episode 6)
The “places” of what may be the series’ most formally inventive episode
are not, literally speaking, very far: Plattsburgh, N.Y., near the
Canadian border, is as exotic as it gets. Yet the succession of three
stories, each set within the same 24-hour period in the summer of ’66,
suggests a time-traveler’s journey: in the space of an hour we visit
war-torn Europe by way of Mars, 1919 Chicago by way of a little acid,
Don’s uncertain future by way of his inglorious past. An extended
snapshot of people living long ago and far away, “Mad Men” is a child in
time—full of reminders that the characters don’t know how their
stories will end. The superb “Far Away Places” phrases it more
succinctly. “Would you say it’s a delightful destination?” Don asks
Megan after lunch in an upstate Howard Johnson’s. “It’s not a
destination,” she replies. “It’s on the way to someplace.”

6. “Meditations in an Emergency,” Season 2 (Episode 13)
“Now I am quietly waiting for the catastrophe of my personality to seem beautiful again, and interesting, and modern,” Frank O’Hara writes in the titular poem, and as in “The Grown Ups” it’s dovetailing catastrophes, personal and political, that define “Meditations in an Emergency.” Here, in the midst of the Cuban Missile Crisis, “Mad Men” offers an unflinching examination of how communities large and small fracture or fuse in times of trouble—as Betty’s friend, Francine (Anne Dudek), bickers with a fellow customer at the hair salon, or Pete, perhaps surprisingly, warns Don of Duck’s plan to subordinate creative under media and account services after the merger with Puttnam, Powell, and Lowe. There’s dark humor (St. John Powell, played by Charles Shaughnessy, quips that Duck “never could hold his liquor”) despite the fear of total annihilation, but the episode culminates in Peggy’s daring, wrenching confession to Pete that she gave their baby away. “One day you’re there, and then, all of a sudden, there’s less of you,” she explains, suggesting both the problems and the possibilities of reinvention with which the series has been so long obsessed. “And you keep thinking, maybe you’ll get it back. And then you realize, it’s just gone.”

5. “The Suitcase,” Season 4 (Episode 7)
Though Don’s silhouette graces the title sequence, Peggy has always been
his co-protagonist, not to mention co-conspirator, co-worker, and
protégé. “The Suitcase,” a focused two-hander set on the day of Sonny
Liston and Muhammad Ali’s second championship bout, makes good on the
promise of season three’s dazzling conclusion. It’s unhurried and
terribly moving, bundled up with allusions to prior episodes. Duck and
Don fight and his closest confidante, Anna (Melinda Page Hamilton), dies, a series of dissolves carrying her ghostly
apparition into the frame, but the image I most vividly remember is a
close-up of Don’s hand clasping Peggy’s. It mirrors their first close
encounter, near the end of the pilot, reducing the tale of how far
they’ve come together to a beautiful miniature, much like “The Suitcase”
itself.

4. “The Strategy,” Season 7 (Episode 6)
As the first half of the series’ final season unspooled, glimpses of the old “Mad Men” genius failed to prepare me for the breathtaking simplicity
of “The Strategy.” Bob Benson offers Joan a marriage of convenience and Pete argues
with Trudy over their failed relationship, but the episode’s
heart resides in a pair of gorgeous compositions focused on connections
strengthened, not severed. As Peggy and Don
sway along to Sinatra’s elegiac “My Way,” or chuckle with Pete under the
Burger Chef roof, the series lands once more on the line between
nostalgia and regret. Indeed, as “Mad Men” concludes its
ambitious portrait of midcentury America, Peggy’s description of her
eponymous strategy—finding family in this “clean, well-lighted place”— reminded me of nothing so much as Don’s, and the series’, defining
moment: “The Wheel.”
 
READ MORE: “The Top Ten TV Episodes of 2014”

3. “The Other Woman,” Season 5 (Episode 11)
“You’re talking about prostitution,” Joan tells Pete about Jaguar salesman Herb Rennet’s (Gary Basaraba) indecent proposal in
“The Other Woman.” “I’m talking,” he replies, “about business at a very
high level.” Mistaking their coercion for negotiation, the partners
acquiesce to the “dirty business” of landing a new account, and in the
process launch SCDP toward its moral nadir. Gorgeous and deeply
unsettling, the episode suggests that the misogyny on display in the
Jaguar campaign (“At last, something beautiful you can truly own”)
creates an atmosphere in which possession includes people as well as
products. Cutting between Joan’s impossible “choice” and Don’s
lascivious pitch, her scarlet lips matching nothing so closely as the
sports car’s alluring frame, “The Other Woman” powerfully illustrates
the consequences of forgetting that everything has a price—especially when that price can’t be measured in dollars.

2. “The Wheel,” Season 1 (Episode 13)
The climax of “The Wheel” takes place in a darkened conference room,
images of Don’s happier days streaming past on the screen before him.
“Teddy told me that in Greek, ‘nostalgia’ literally means ‘the pain from
an old wound,'” he says to a pair of Kodak executives, referring to an
early mentor. “It’s a twinge in your heart, far more powerful than
memory alone. This device isn’t a spaceship; it’s a time machine. It
goes backwards and forwards. It takes us to a place where we ache to go
again. It’s not called ‘The Wheel.’ It’s called ‘The Carousel.’ It lets
us travel the way a child travels, around and around and back home
again, to a place we know we are loved.” In closing the circle,
“The Wheel” perfectly encapsulates the “Mad Men” ethos—tracing the
thin line between nostalgia and regret, mining the ache that accompanies
memory’s pull and time’s forward march. History is always hovering
around the series’ edges, but the moving finale to season one points to
the fact that “Mad Men” is as much about how we (mis-) remember the past
as it is about the past itself.
 
1. “Waterloo,” Season 7 (Episode 7)
Though I called “The Strategy” the best television episode of 2014, though the two work in tandem to assert a powerful argument that mass culture is, as Don once said about
Hershey’s, “the currency of affection,” I’ve since come around to “Waterloo” as the series’ greatest achievement. From the murmur that accompanies Peggy’s brilliant, powerful Burger Chef pitch to Bert Cooper’s memorable musical farewell, “Waterloo” conveys much of what watching television means to me. This is, after all, both what “Mad Men” is and, in a sense, what “Mad Men” is about: the thoroughly modern ways by which we forge relationships despite the niggling feeling that the center cannot hold, the capacity of culture to reflect, refract, unite, and divide us by offering some shared terrain for conversation. Our own landscape may not be the seeming monolith of the moon landing, but “Mad Men” squared a space nearly as vital for the discussion of who we are and who we hope to be. As the episode arrives at the moment we’ve learned to remember, in
the form of Neil Armstrong’s iconic words, the camera captures both the
glow illuminating the characters and the blurry, black-and-white
pictures of those first celestial steps. The television is, appropriately enough, presented as
a locus of human connection and sincere emotion: a clean, well-lighted
place, as Peggy says in “The Strategy,” much like “Mad Men” itself.

The “Mad Men” marathon begins tonight at 6pm on AMC. The series finale airs Sunday, May 17 at 10pm.

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