10. “Commissions and Fees” (Season Five, Episode 12)
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
9. “Smoke Gets in Your Eyes” (Season One, Episode 1)
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
8. “The Strategy” (Season Seven, Episode 6)
“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
7. “The Other Woman” (Season Five, Episode 11)
“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
6. “The Crash” (Season Six, Episode 8)
“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
5. “The Wheel” (Season One, Episode 13)
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
4. “Waterloo” (Season Seven, Episode 7)
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
3. “Guy Walks into an Advertising Agency” (Season Three, Episode 6)
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
2. “Shut the Door. Have a Seat.” (Season Three, Episode 13)
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
1. “The Suitcase” (Season Four, Episode 7)
“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