The 5 Best Episodes of Mad Men

From the moment a blank silhouette first came tumbling down in a cityscape free-dive in an oft-imitated credits scene, Mad Men grabbed its viewers by the collar and guided them along what would become an eight-year journey freckled with a flurried mix of cocktails, cigarettes, scintillating behind-closed-doors affairs, and, above all that, existential questions of morality, identity, and what it means to live in truth. It made many of us mad for it all. Though we’re hardly to blame.

The series, borne from the mind of former Sopranos scribe Matthew Weiner, splayed out its narrative in a sequence similar to the sketchings on a heart monitor: bursting forth in moments of intense emotion, then dipping into the troughs of suburban ache and the lingering fear of fire that comes with burning a past life to the ashes, only to swing up to the highest steeple for a stretch of triumphant character conquests. It kept us captivated, kept us craving.

Nothing reminds Mad Men fans of that simple truth more than these instances of remembrance—especially the aluminum anniversary this year brings: ten years since Mad Men’s inaugural episode. To celebrate the successes the cast, crew, and creatives of Mad Men have basked in over the last decade, and to honor the masterpiece the series so clearly is, we’re taking a look back at the five best episodes in Mad Men history.

5. “Shut the Door. Have a Seat.” (Season 3, Episode 13)

Tense and unexpectedly electrifying, the season three finale of Mad Men touts a plot so airtight, it could survive a Biblical flood. And that’s exactly the kind of monumental chaos against which the Sterling Cooper clan was bracing themselves, but ended up self-sparking with an eye-widening exit strategy that gave way to a new company, featuring two new names, and allowed for the birth of a new era.

“Shut The Door. Have A Seat.” may borrow boldness from Don Draper’s (Jon Hamm) signature line used to indicate an impending firing, or worse, but it delivers its own brand of badassery in plot, pacing, and the portrayal of the series’ central characters. When the fabric of Sterling Cooper is ripped from underneath Don, Joan (Christina Hendricks), Peggy (Elisabeth Moss), Lane (Jared Harris), and Roger (John Slattery) in what was a money-making business merger, the foursome lay a carpet toward a bigger dream. But it’s one stained with heartache amidst the heroic feat of starting fresh—a sour twinge which makes the episode a standout in Mad Men’s pantheon.

First, there’s the a three-peat of happy moments: 1) Feeling the effects big business has had on their once-pure friendship, Don and Roger truly speak to each other, for the first time in a long while, and decide the broken bits aren’t irreparable. 2) Peggy, yet to rise to the heights she reaches in later seasons, shows her vulnerability to Don in saying she feels like a “nervous poodle” at the thought of founding SCDP. 3) Pete (Vincent Kartheiser) suddenly loses his will-I-won’t-I mentality and learns he’s truly needed.

Layered between this trio is a double dose of ugliness: 1) Betty (January Jones) slams her proverbial fist on the table, demanding a long overdue divorce from Don and expressing a desire for her own clean slate. If Don can do it with SCDP, why can’t she do it with the dashing Henry Francis? 2) An alcohol-fueled argument, followed by the heartbreaking conversation that breaks the Draper family in two.  

In all, “Shut The Door. Have A Seat.” will always be remembered for its ability to marry well-deserved elation with the realities our characters could never escape. And, of course, for giving us this line: “There are people out there who buy things. People like you and me. And something happened. Something terrible. And the way that they saw themselves is gone. And nobody understands that. But you do.”


4. “Guy Walks into an Advertising Agency” (Season 3, Episode 6)

From that heaviness comes something markedly lighter: the dryly humorous, smartly shot, and undeniably witty sixth episode of Mad Men season three. With a title that sounds straight from the list of Friends episodes (this could totally be called “The One with the John Deere Lawn Mower”), “Guy Walks into an Advertising Agency” subverts the usual slow-burning tempo of the series and sets it ablaze. Or, more appropriately, gets it drunk, chucks it the keys to a high-powered, bladed lawn tool, and sets it loose inside a packed office.

It sees Ken Cosgrove (Aaron Staton) land an account with John Deere, and, naturally, bring in one of the company’s lawn mowers to the Sterling Cooper offices as a way of celebrating. (Hey, there’ve been wilder things than just machines inside those walls.) Liquor begins flowing and so do tears, as Peggy prepares to say goodbye to Joan, who was poised to depart from Sterling Cooper  following her husband’s promotion to Chief of Surgery. All hell breaks loose, and the emotional weight of the women’s conversation gets completely undercut when well-meaning (and completely unlicensed) switchboard operator turned secretary Lois (Crista Flanagan) makes a little too much of her liquid courage. She drives Ken’s lawn mower directly over the foot of Guy MacKendrick, the Brit intended to dethrone Lane Pryce as head of Sterling Cooper.

In a moment that would make Quentin Tarantino proud, blood sprays across Harry Crane (Rich Sommer) and Paul Kinsey’s (Michael Gladis) unsuspecting faces and crisp white dress shirts. And in another that solidifies “Guy Walks into an Advertising Agency” as one of Mad Men’s finest and funniest episodes, Roger quips, “Jesus! It’s like Iwo Jima out there!”

3. “The Wheel” (Season 1, Episode 13)

Man’s most fundamental invention and one of Mad Men’s most poignant outings, “The Wheel” encapsulates greatness by the series’ specific standard and by that set by television the world ‘round. That juice is found in a single scene: the carousel.


Lauded for its gauzy imagery (that heartbreakingly beautiful montage of Betty and Don’s blissful early days) and deep symbolism (the cyclical nature of life that so often feels like a merry-go-round), the carousel sequence shows the viscerality of both Don’s marketing prowess and his inescapable past. What infuses this moment, and the entire episode, with additional resonance is the knowledge that Don’s tear-jerking pitch to Kodak came just hours after discovering his brother had committed suicide—a tragedy largely driven by Don’s adamant refusal to acknowledge his former life.

Cushioning this isolated incident of ingenuity are a handful of highlights, namely the brilliantly juxtaposed success (a promotion!) and sadness (labor pains!) Peggy experiences, Betty’s subdued speculation that Don is hiding something from her, and Don’s return home to an empty house on Thanksgiving Day.

As any Mad Men loyal will agree, “The Wheel” is at once a defining moment in the show’s history, an incredible close to the first season, and an episode worthy of that sought-after “prestige television” stamp.

2. “The Other Woman” (Season 5, Episode 11)

While Mad Men has featured a handful of its central characters’ other women, this season five episode isn’t so much about clandestine lovers (though the plot centers around a proposition for a relationship of that type) as it is about Joan and her so-called other woman: Peggy.


Pete, ever feeling second best at Sterling Cooper and perpetually on the hunt to prove himself, capitalizes upon his innate ability to be smarmy in efforts to help secure a slick new account. His plan? Pass Joan off as a courtesan clacking her heels on the Madison Avenue pavement, and get her in the hands of Herb, the Jaguar client in question. Don, admittedly not the best voice of reason amongst the series’ coterie in this particular regard, publicly rejects Pete’s proposition and makes a valiant attempt at stopping him from actually doing it. Unfortunately for what little remains of Don’s conscience, his protestations fall on deaf ears, and Joan agrees to get frisky with Herb in exchange for a portion of the company and a swanky promotion to a partnered member of the agency.

From here, Joan proves she’s light years ahead of the men who surround her, whisper into her ears, try to counsel her. She knows that in life, you often have to commit to things that are unpleasant (though we wouldn’t condone prostitution as a means) in order to obtain you truly desire. For Joan, the degrading act secures her a future in which she’ll never be stripped of her dignity again. Her path to greatness is paved with sacrifices, and “The Other Woman” expertly displays that.

It does much the same for Peggy, who began as Joan’s antithesis but soon metamorphosed into both her inspiration and her pupil. As the seasons rolled on, the pair became intertwined and emerged to the forefront, establishing themselves as integral pieces to the action. “The Other Woman” shows the differences that exist between the dynamic duo—Peggy slaving over her typewriter, Joan likely dripping in sweat as she’s dripping in jewels—and affirms a common ground from them: Joan and Peggy will stop at nothing to get what they want. For the former, it’s a seat at the table she’s more than qualified to head; for the latter, it’s much the same.

Selfishly, I adore this episode because it contains what I consider the very best scene in Mad Men’s glorious history: the goodbye between Don and Peggy that plays out like a microcosm of the dynamic of their relationship. Don’s quippy, talking business, at the start; Peggy throws beneath him an undercurrent of emotion in setting up the reveal that she’s leaving the agency. A few lines into the conversation, and the two meet each other in the middle—as they always seem to. Don’s somewhat cold exterior melts; he’s visibly shaken. Peggy tries to put an analytical spin on her departure; she lists her leaving plan point by point. It’s a game of verbal cat-and-mouse, and it’s a scene I can’t get enough of.

1. “The Suitcase” (Season 4, Episode 7)

We’ve reached the end of the road, and what would a “best of Mad Men” list be without a mention of the most beautiful episode of all? “The Suitcase” qualifies as the pinnacle of Mad Men mysticism, but simply calling it an episode of a television series is a great disservice. Its winsome and intimate depiction (which feels almost like a dedication) to Don and Peggy is cinematic, building to an ultimate epiphany that retroactively influences our understanding of episodes past and shapes the way we view those yet to come.

With passionate conversations and one mini breakdown in the bathroom, “The Suitcase” substantiates the love, care, and respect Don and Peggy have for one another. These feelings have long lingered on or just below the surface of the narrative, remaining a semi-known truth never actualized. And more importantly, their relationship is never consummated—though it easily could have been. Sex is a weapon for Don, and for Peggy, it’s something wrapped in shame and guilt following the birth and subsequent giving-away of the child she had with Pete. By having Don and Peggy abstain from the physical act that drives so many plotlines in Mad Men, it preserves the fragility of their protégé-prodigy relationship (of which the roles began to reverse in later seasons) and allows for a full-circle dual character arc to come around in the series finale.

Touching, affecting, and so important “The Suitcase” sums what the series is really all about: a lost man and his best girl trying their damnedest to make it through the mad, mad world in which they live.


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