Ten years after the debut of Mad Men, which Paste celebrates here by paying homage to the series’ 20 best episodes, Matthew Weiner’s period drama, starring Jon Hamm as dashing ad man Don Draper, still stirs the electric sensation of first seeing “Smoke Gets in Your Eyes.” To watch its finest entries again now—particularly its later ones, which broaden and deepen its portrait of midcentury America and so dominate this list—is to be reminded that its association with TV’s latest “Golden Age” is actually rather limiting. Often darkly hilarious, almost always astute, boldly “cinematic” (for lack of a better term), and defined by its peerless attention to character, Mad Men is rightly considered one of the great TV series of its (or any) era, but not because of the gloss of “prestige.” The magic of “Mad Men” is that it brings one to tears over “Family Supper at Burger Chef” as if we were among those being pitched, but its genius was that its acknowledged it was always pitching us — “You are the product: you, feeling something” — and still managed to pull it off.
In the haunting finale of Mad Men’s fifth—and finest—season, the series arranges all that’s lost into a series of visitations: Don’s deceased half-brother, Adam (Jay Paulson), appears along with the ad man’s hot tooth; Pete (Vincent Kartheiser) drops in on his illicit love interest (Alexis Bledel) in the hospital, her memory fuzzed by electroshock therapy, to discuss the life he’s built, and broken; in the aftermath of Lane’s suicide, Joan (Christina Hendricks) glances at his empty chair in an otherwise optimistic board meeting. “The Phantom” constructs these interludes of regret with such poignant force that even the heavy-handedness of certain symbols (“It’s not your tooth that’s rotten,” Adam says to Don) cannot sink its portrait of the past’s death grip on our lives, culminating in perhaps the series’ most evocative image, one that never ceases to astonish me: As Don and the camera retreat from Megan (Jessica Paré) on an ad spot’s sound stage, the illuminated proscenium receding into the distance, Mad Men pries open the space between who we are and who we hope to be in searing terms. “You only live twice,” Nancy Sinatra sings as the season comes to its bitter close. “One life for yourself, and one for your dreams.” Matt Brennan
Although Mad Men was a story about life in the 1960s, it only occasionally showed the direct impact that decade’s events had on its characters. This is not the case here, as writers Matthew Weiner and Brett Johnson offer a reminder that not every upper class New Yorker would have had the same reaction to JFK’s assassination. As the rest of the world stood still, Duck (Mark Moses) isn’t about to let a little thing like televised murder get in way of his affair with Peggy (Elisabeth Moss), and he switches off the hotel’s set as the news breaks before she arrives. Yet Brownoser-in-Chief Pete Campbell is shaken up enough to miss his boss’ daughter’s wedding (this may partly be because he’d also just lost a promotion). And January Jones’ Betty? It took watching a weekend of bloodshed in Dallas for her to accept that life’s too short and she wants out of her marriage. Whitney Friedlander
There are so few instances in Mad Men’s seven-season run of Don Draper truly, fully losing control of himself in front of others that when Betty finally (finally!) detonates their powder keg of a marriage and confronts him over his past after nearly three seasons, it’s like we’re watching a different man entirely. Of course, in many ways, we are; once he knows he’s been caught, the smooth ad man wilts and reverts back to scared Dick Whitman. Even Betty seems stunned by how shaken he is; his hands are trembling so badly he can’t even hold on to the cigarette he’s fumbling for to calm his nerves, so she takes pity on him and offers to get him a drink. It’s the confrontation the series had been building up to for three years, and it does not disappoint. Betty knows everything, or nearly so—she doesn’t know Sally’s teacher/Don’s side-piece Miss Farrell (Abigail Spencer) is sitting in the car outside her home waiting to run away with her husband while this whole conversation is happening—and by the time the whole thing culminates with a guilt-stricken Don weeping over his brother Adam’s suicide, we have no idea where the Drapers stand. It’s fitting that the episode ends on Halloween, as Sally and Bobby take their own stab at trying on new identities for a night, dressing as the titular gypsy and hobo (both nomads, like their father). When the man passing out candy looks Don in the eyes and asks, “And who are you supposed to be?” his smile fades, and it’s obvious he’ll be spending most of Season Four trying to answer. Bonnie Stiernberg
In “Lost Horizon,” everyone is facing the end of SC&P as they know it. Almost as soon as Don gets to the McCann Erickson office, he leaves to begin the walkabout that ends the series. Joan has a quieter, sadder ending with the company, leaving with half the money she’s owed and trying to hold on to as much dignity as she can. Peggy’s walk down the hallway to her new office, with a cigarette hanging out of the side of her mouth and an obscene painting under one arm, is the culmination of years of earning her swagger. It’s one of the most satisfying moments in the final season. “Why are you still here?” is a question asked repeatedly throughout “Lost Horizon,” and Peggy may be the only one who knows the answer. Rae Nudson
Betty and those birds, man. “Shoot” gives us one of the first great Betty Draper-centric episodes of Mad Men and—beyond that—one of the single most memorable images of the series, as the episode ends with the dead-eyed housewife plucking her neighbor’s pigeons out of the sky one by one with a BB gun with a lit cigarette dangling from her mouth. Earlier in the episode, with some encouragement from McCann Erickson’s Jim Hobart (H. Richard Greene), who sees her as a pawn in his plot to poach Don from Sterling Cooper, she decides to return to modeling, playing up her Grace Kelly-esque looks for two days of Coca-Cola photo shoots. Don’s not exactly wild about the idea, and he’s disgusted that Hobart would sink so low as to convince his wife to return to work to try to lure him to McCann (sigh), so he negotiates a raise at Sterling Cooper. Of course, Don’s decision to stay results in Betty’s modeling dreams being dashed—she’s no longer of any use to Hobart—and we’re presented with a devastating scene in which she lies to Don, making it seem like she decided on her own to stop modeling and insisting through a pained smile that she has all she ever wanted right at home. She puts on a brave face and a pink housecoat the next morning, and it’s almost eerie how Stepford Wife-y she seems as she does a few chores and gently reminds the kids not to jump off the bed. But soon enough, she’s outside taking out all her pent-up frustration out on those birds. She’s protecting her home, sure (the neighbor had made a threat against the Drapers’ dog), but what makes the final image of “Shoot” so stunning is that we know Betty’s acting out of jealousy. Those birds represent the freedom lacking in her life, and while Don’s enjoying a pigeon-similar existence—soaring through life, not tied down by a contract or anything else, for that matter—she’s stuck at home, trapped by an unhappy marriage and a society that views her as nothing more than a face. They have what she never can, and so Betty Draper calmly, cooly takes aim and tears them down. Bonnie Stiernberg
“Not great, Bob!” There’s not a television phrase I’ve worked into my lexicon more than this delicious bon mot, perfectly delivered by Pete Campbell to that snake in the grass Bob Benson (James Wolk). For that elevator moment alone, this episode deserves a space in our Top 20. But the sixth season finale also offers searing epiphanies for several key players. Ted Chaough (Kevin Rahm) realizes he must move to Los Angeles to put an end to his affair with Peggy. And, after years of keeping his identity a secret, a world-weary Don has a breakdown in the Hershey’s pitch, confessing to all that he was raised in a whorehouse. That moment leads to Don’s (temporary) suspension from the firm. Most importantly, the episode ends with Don showing his three children where he actually grew up. Don and Sally (Kiernan Shipka) share a glance of mutual understanding. Don is not who she thought he was, but maybe now he can be who she needs him to be. Amy Amatangelo
Pop quiz: Name a television character equally as loathsome and pitiable as Pete Campbell. Trick question! You can’t, because there isn’t one. He’s a schemer, a creeper, an egotist, a liar. He’s the real thing. Throughout Mad Men’s history up to “Signal 30,” nobody in Campbell’s orbit has felt fussed enough to pay him what he deserves beyond roasts and insults. It’s Lane Pryce (Jared Harris), perhaps the most unexpected member of the show’s cast, who finally puts Campbell down and in his proper place, on the floor, his nose bleeding, the pride he’s compiled throughout the episode utterly ruined. As moments go, this one is pretty satisfying, but the great trick of “Signal 30” is that we’re all left to puzzle at the morality of letting two men beat the tar out of each other in an office environment.
“I know cooler heads should prevail,” Roger (John Slattery) says, voicing aloud what we’re all thinking, “but am I the only one who wants to see this?” He isn’t, naturally, but the empathy “Signal 30” generates for its least likable character is staggering; it’s one thing to hear Pete’s peers shit-talk him or give him a dressing down, to see him fail at his every attempt to emulate Roger and Don, and another thing entirely to see him so humiliated, stripped of his self-assured veneer of faux-manhood. It’s actually kind of painful. Andy Crump
You’d be forgiven for thinking them too tightly structured and too thematically overdetermined, but the best episodes of Mad Men often felt less like TV and more—and here one should take care not to groan too loudly—like filmed short stories. That’s certainly the case with “Far Away Places,” which plays like a triptych about intimacy. Folding unto itself not once but twice, the episode takes place during one day: We follow Peggy as she tries to Don her way through a pitch gone awry; Don as he tests the limits of his domineering relationship with new wife Megan; and Roger as he lets himself be led down an epiphanic LSD trip by his own young wife, Jane (Peyton List). It’s all punctuated by dreamlike visuals that lend the proceedings a discomfiting sense of foreboding that permeated Mad Men’s vision of the tail end of the 1960s. Manuel Betancourt
In the Season Two finale, the world nearly ends, and everyone has to decide where they want to stand when it comes. Betty struggles with the personal doomsday of a pregnancy she does not want with a man she no longer likes. SCDP is in upheaval over Duck Phillips’ plan to become the agency’s president, which backfires on him pretty spectacularly. Few Mad Men moments are as iconic as Don casually saying he doesn’t have a contract for SCDP to enforce. The scene that truly makes this episode, though, finds Peggy finally coming clean to Pete that she had his baby. Peggy’s confession that she “wanted other things,” and her attempt to explain the feelings of loss and acceptance she has experienced, is so quietly devastating it still gives me chills all these years later. Sara Ghaleb
“Mystery Date” might be said to define Mad Men’s definition of “the episode”: It sets down now-familiar characters in new, and unsettling, historical context—an eruption of riots in cities across the country and a “student nurse massacree” in Chicago, as Zosia Mamet’s Joyce so memorably puts it—then watches as their reactions to circumstance court, spark, and finally catch fire. It’s wickedly, wildly funny: “Hey, Trotsky, you’re in advertising,” Roger snipes at Peggy, after approaching her with an under-the-table assignment. It’s impossibly lurid: Ginsburg (Ben Feldman) lashes out at his colleagues for being titillated by images of “girls trussed up like a cut of meat.” It’s densely allusive (the title comes from a contemporaneous board game) and visually stunning (Don’s murderous dream sequence is punctuated by the overhead image of a garish pink pump). Most of all, though, it prickles with the dangers women face, day in and day out, at the hands of men, shadowed by the notion that our culture’s fantasies of women as “wounded prey,” to quote Ginsburg’s “dark Cinderella” pitch, are complicit in the frequent, all-too-real relationship between sex and violence. Matt Brennan
While Mad Men is often about gradual, incremental change, “Commissions and Fees” drops the floor out from under its characters and changes their lives irrevocably. Sally becomes a woman in a moment of parental defiance, the beginning of an important change that is scary, yet necessary. But for Lane, his firing from the company he helped start is an inconceivable weight to bear: a sign of shame, to which the man who tried so hard to achieve the American Dream reacts by hanging himself in his New York City office, while a replica of the Statue of Liberty watches from his desk. “Commissions and Fees” is one of the more shocking episodes of Mad Men, from Lane’s morbidly humorous failed suicide attempts to his former coworkers finding his body. Yet it’s Don’s reaction that hits the hardest—Don, the man who told Lane how easy it is to move on, then paid away Lane’s debt as if it was nothing. Don lost his brother in a similar situation—a hanging brought on by money problems—and with Lane’s passing, it’s almost as if we witness Don losing his brother all over again, another death he could’ve avoided. Ross Bonaime
It would, perhaps, be too hyperbolic to say that Mad Men’s pilot is perfect. But there’s no denying it’s a perfect version of what Mad Men would become. There’s the plush attention to period detail; the thematically weighted music cues (Nat King Cole’s “On the Street Where You Live” closes the episode); the near literary sense of dialogue (“You think I’d make a good ex-wife?”); even the refreshing, if oft-ignored, feminisms the show takes care to represent. It’s all there, wrapped up in a character study of a man vexed by his own ambition and insecurity, and who fears his time may be running out. Weiner’s show wasn’t ever just about Don Draper, but as its pilot shows, it was all too happy to frame itself around him, making him into what midcentury life was, could, and longed to be. Manuel Betancourt
“There’s always a better idea,” Stan (Jay R. Ferguson) tells Peggy as she obsesses over finding a new pitch for Burger Chef even though she already has a perfectly good one. That theme carries through the episode, as everyone seems eager to throw away perfectly good plans just to chase something they might not get. Pete ditches his girlfriend to see Trudy (Alison Brie) again and, in a classic Pete Campbell move, sticks a beer bottle in her cake. Joan rejects Bob Benson’s proposal of a loveless marriage, not caring whether it’s her last offer. Don and Megan do their Don and Megan strained denial thing. This time, though, Peggy does get a better idea—and a happy ending, of sorts. As the episode closes on Don, Peggy, and Pete’s dysfunctional, workaholic family unit sharing a meal, it’s easy to believe that the chase is worth it. Sara Ghaleb
“The Other Woman” sets in motion a three-episode arc (continuing in “Commissions and Fees” and concluding with “The Phantom,” both of which appear on this list) in which Mad Men is at the height of its powers, a portrait of capitalism’s forms of “courtship” that conjures no small amount of revulsion. There are innumerable grace notes, of course, in particular the touch of Don’s lips to Peggy’s hand as she departs for Cutler, Gleason and Chaough, but the thrust of the episode is the indecent proposal slimy dealership owner Herb Rennet (Gary Basaraba) offers SCDP: a night with Joan, in exchange for his support of the firm’s Jaguar pitch. It’s Hendricks’ finest hour on the series, deftly navigating Joan’s multifaceted reaction; she ultimately swallows the poison pill of humiliation and coercion, though it’s unclear whether she does so because of the promise of financial security for her and her son, because she believes none of the partners protested, or (most likely) both. The climactic montage, toggling between Joan’s encounter with Herb and Don’s lip-licking pitch (“At Last, Something Beautiful You Can Truly Own”), draws wrenching connections between person and product, the red of Joan’s hair reflected in the red of the car, and the result is one of the series’ most searing condemnations of deranged values. “Don’t fool yourself,” Roger, no innocent in the matter, says after the partners agree to approach Joan with the offer. “This is some very dirty business.” And he’s right. Matt Brennan
“The Crash” is arguably the most symbolism-heavy episode of an extremely symbolism-heavy series; there is so much to unpack, we can only scratch the surface here in this blurb (fortunately, I took a lengthier stab at it here). The entire thing can be read as an allegory for the Vietnam War, with the agency worn down by the impossible, un-winnable Chevy account. (Don tries to rally the troops with a drug-fueled “In my heart, I know we cannot be defeated.” Much of the cast is dressed in green or brown, and Stan in particular, who reveals he lost a cousin in the war and is later wounded himself after facing a William Tell-inspired firing squad, looks like a POW when he’s got his tie around his eyes like a blindfold. Ginsberg—who is the only sober one after everyone else in the office besides Peggy gets hopped up on speed and she gets drunk—serves as the show’s conscientious objector. There are even casualties, as Ken gets wounded while courting Chevy and Frank Gleason finally dies of cancer.)
But beyond that, we get some creepily Oedipal flashbacks where we see young Dick Whitman sort of unwillingly lose his virginity to a prostitute who acted as a mother figure to him and nursed him back to health when he had a chest cold and gain a much clearer understanding of why Don chooses the women he chooses and makes the mistakes he does. It’s why he chose Megan over Dr. Faye after watching her clean up his kids’ spilled milkshake in Season Four, and it’s definitely why he’s now cheating on her with Sylvia (Linda Cardellini)—if that wasn’t apparent earlier, Matthew Weiner hammers it home for us with that soup ad Don spends the episode searching for. The copy reads “Because you know what he needs,” which can have an innocent motherly meaning or a more sexual one, and the woman pictured is wearing a bandana and sporting the same birthmark as the hooker who deflowered Don. Sylvia’s seen earlier in the episode wearing a bandana and cooking for her husband, and she’s got that same birthmark. Yikes. “The Crash” feels completely surreal, and it’s easy to get distracted by all the crazy shit, like Stan making a move on Peggy, Ken doing that manic tap-dance, or Don on amphetamines sternly insisting that “The timbre of my voice is as important as the content.” But ultimately, it all comes back to Peggy’s Wordsworth reference: “The child is the father of the man.” Our antihero, who’s previously spouted off lines like “It will shock you how much this never happened” and been so keen to move forward that he literally reinvented himself and left his past behind, has discovered that those who don’t pay attention to history are doomed to repeat it. Bonnie Stiernberg
This episode may be best remembered for Don’s speech about nostalgia and the Kodak Carousel slide projector, but it’s Betty’s slow meltdown that makes it one of the best. Don’s been peddling fantasy to her for years, but in “The Wheel,” Betty is forced to face reality. She finds out her friend’s husband is having an affair, and she tells her psychiatrist she believes Don is unfaithful. The depth of her sadness is clearest when she confides in Glen (Marten Holden Weiner), a child who worships her in a way Don never will. Other big events in this episode include Peggy having her baby and Don finding out his brother committed suicide. Everything that happens in “The Wheel” touches on reality versus fantasy, and it’s not always clear which is which. Rae Nudson
It is difficult for me to express my adoration of “Waterloo,” except to say that it is, for me, the episode that renders the meaning of Mad Men most forcefully. It’s arranged around three note-perfect sequences, each focused on the relationship between the artful and the commercial, the personal and the historical, the fictive and the real. As the characters stare, mouths agape, at the moon landing, or as Bert Cooper (Robert Morse) turns in a spectral performance of “The Best Things in Life Are Free” for Don, the series offers yet another masterly assessment of what we want, and how we get it, and why it is we can’t. At the heart of the episode, though—at the heart of Mad Men entire—is Peggy’s brilliant Burger Chef pitch, in which Don passes the torch to his longtime protégé (“Every great ad tells a story, and here to tell that story is Peggy Olson”) and watches, in awe, as she delivers a moving tribute to the power of popular culture. Mad Men might be the TV series most alive to the medium’s problems and possibilities, its ambivalent negotiation between salesmanship and sentiment, and Peggy’s description of the astronauts setting foot on another world is run through with the recognition that the moment is as consequential for its earthly implications as it is for its celestial ones. “We can still feel the pleasure of that connection,” she says, condensing Mad Men’s sublime ambition to a single sentence, “because, I realize now, we were starved for it.” Bravo. Matt Brennan
Much like Matthew Weiner’s previous gig, The Sopranos, Mad Men was often at its best when it was funny. This point is proven with this mid-season wonder, where even the title is the set-up to a joke. Written by Weiner and his frequent early-season collaborator, Robin Veith, and directed by eventual Homeland genius Lesli Linka Glatter, “Guy Walks…” continues the storyline of an evil English ad agency’s pending invasion and our beloved Joan’s preparations for her last day at work. It ends with only part of those things happening, thanks to an American welcome that would have made Paul Revere proud: a dashing British ad executive loses his foot to a renegade John Deere mower (the property of Aaron Stanton’s Ken Cosgrove, who would later lose his eye while securing another account—a delicious piece of foreshadowing). Whitney Friedlander
What is a finale for? Resolving story threads and setting up the next season’s course, or throwing the series entirely out of balance via creative upheaval? “Shut the Door. Have a Seat.” favors the latter definition, warping our expectations of Mad Men’s future by adopting a style from way, way outside the series’ regular purview, and by discarding its narrative’s normal state of affairs. If Mad Men, as a story, is all about exterior cool overlaying interior woes, anxieties and neuroses, then “Shut the Door. Have a Seat.” is all about embracing the cool in the interest of plot deployment. Think Ocean’s Eleven, but with a smaller scale, even better suits, and infinitely more psychological baggage.
Taking a caper blueprint and honing the scope down to Mad Men’s level doesn’t rob the caper of excitement, though, and “Shut the Door. Have a Seat.” is nothing if not exciting. On top of that, it’s thoroughly sanguine, which in Mad Men terms is as much a twist on formula as the hero beating the villain is for Game of Thrones. Let’s be clear, though: Cheer in any installment of Mad Men is anchored, always and forever, by gloom, in this case John F. Kennedy’s assassination, seen in the previous episode, “The Grown-Ups,” and felt in the finale as Don and Betty’s marriage finally gives up the ghost, McCann Erickson buys up Puttnam, Powell, and Lowe, and Sterling Cooper Draper Pryce rises from the ashes of Sterling Cooper.
Death’s fingerprints are all over “Shut the Door. Have a Seat.” whether figuratively or literally. But the sense of loss lies at the episode’s core. Everything else, that’s all about rebirth. It takes a lot of chutzpah to fundamentally alter the texture of your hit TV series just a few seasons into its lifespan, and that’s the key to the episode’s greatness as a season ender. It’s the point where everything, and yet nothing, changes for Mad Men, until its final hour. Andy Crump
“The Suitcase” stands out from the rest of the series for a number of reasons, but most noticeably, it’s the closest Mad Men ever got to a bottle episode, an opportunity for a show so known for its elaborate, era-specific sets and costumes to scale back any potential distractions and simply let its two leads flex their acting muscles. It’s the TV equivalent of your favorite rock band unplugging and completely knocking you on your ass with a gorgeous, acoustic ballad. The legendary fight between Sonny Liston and Muhammad Ali serves as the backdrop for “The Suitcase” as the show pits its own two heavyweights against each other after-hours at work. Unlike the boxers, however, they both last more than one round, airing some longstanding grievances and delivering some of the show’s best lines (see: an irate Don spitting, “THAT’S WHAT THE MONEY’S FOR!” after Peggy complains he never says thank you) before reconciling and eventually opening up to one another like never before.
The Liston/Ali parallels are there—Don as the reigning champ, older, believed to be unbeatable; Peggy as Ali, the young, up-and-coming, perhaps overconfident challenger who’ll eventually beat the odds and knock him out. But instead of standing over her fallen opponent like in the iconic Ali photo from which they wind up drawing inspiration for their Samsonite ad, Peggy winds up cradling his head in her lap because “The Suitcase” is ultimately a beautiful showcase for their platonic friendship, highlighting what makes them so similar and demonstrating how they drive each other to be better. Jon Hamm and Elisabeth Moss both turn in some of their best performances of the series (if a weeping Don lamenting that the recently-dead Anna was “the only person who ever really knew me” only to be assured by Peggy that “that’s not true” doesn’t get you every time, you have a heart of stone), and “The Suitcase” stands as one of the best episodes of television ever. Bonnie Stiernberg