10th Anniversary Retrospective: 10 Best Episodes Of Mad Men – Ranked

Nostalgia – it’s delicate, but potent. 

In July 2007, AMC rolled the dice and came up huge winners as they sponsored Matthew Weiner’s Mad Men, the network’s first foray into series television, which quickly turned into a pop culture phenomenon with an extremely loyal fan base.

Following the careers of the ruthlessly competitive men and women of Madison Avenue, viewers were invited into the spellbinding age of 1960s New York, as seen through the eyes of Donald Draper, a self-made advertising genius who leads a duplicitous life of decadence and deception.

Throughout its stellar seven-season run, the landmark series collected five Golden Globes and 16 Emmy Awards, including three for best drama, making international stars of Jon Hamm, January Jones, Christina Hendricks and Elisabeth Moss.

And so, in celebration of the show’s tenth anniversary, we have cherry picked the ten best episodes – ranking the greatest triumphs from the greatest television drama of all time.

10. The Strategy (S7 E6)

10. The Strategy (S7 E6)

Written By: Matthew Weiner & Semi Chellas Directed By: Phil Abraham

Despite their terminal loneliness, Don Draper, Peggy Olson and Pete Campbell have a lot more in common than they care to admit because they choose to share more mutual secrets than truths – but this is what makes their particular relationship the closest thing to family, for better or for worse. 

So when the dysfunctional trio appear united for the first time in several seasons, during the first half of season seven, we could not help but sob into our handkerchiefs while trying (and failing) to maintain all of the poise and grace of Betty Draper. 

By this point, Don and Peggy have been at odds for so long that we cannot remember the last time they exchanged a genuine smile, but Pete’s return to Manhattan seems to be the turning of the tide, especially in terms of rebuilding their undeniable but head-scratchingly complex bond.

After reluctantly working on the Burger Chef campaign together, the two characters start to restore their connection, and as the night goes on, they open up about their parallel insecurities, both agreeing that the perfect, nuclear family does not exist.

This deep and meaningful conversation culminates in Don finally admitting to Peggy: “I worry about a lot of things, but I don’t worry about you,” before offering to take her hand and dance to Frank Sinatra’s wistfully mournful record ‘My Way.’

This moving moment can only be matched by the episode’s final shot, framed looking through the window of a Burger Chef, with Don, Peggy and Pete seated at a dinner table, breaking bread together, as a non-traditional family in a “clean, well-lighted place.”

9. Waterloo (S7 E7)

9. Waterloo (S7 E7)

Written By: Matthew Weiner & Carly Wray Directed By: Matthew Weiner

Working in tandem with The Strategy, season seven’s mid-season finale encourages viewers to cast the past aside and focus on the future, by way of an episode that orbits around the Apollo Moon Landing while at the same time paying homage to the 1960’s decade.

As we continue to follow the lives of our favourite characters, Sterling Cooper & Partners touch down in Indianapolis, Indiana, prepped and ready to deliver their powerful pitch to Burger Chef, through which Peggy Olson articulates the beautiful line: “You’re starving, and not just for dinner.”

This transformative moment emphasises the underlying message of the episode, which is that happiness is not simply the “moment before you need more happiness” (as cynically defined by Don Draper) but rather, a psychological state that is derivative from the success of a shared endeavour.

Whether it’s winning an advertising campaign or embarking on a flight to the moon, a great leap forward is encountered in this episode, with a whole heap of change for the characters – especially Bertram Cooper who tragically passes away just hours after witnessing the lunar landing.

In a surreal send-off, Don later has a technicolor hallucination of Bert who appears to be starring in his own Broadway musical number, singing and dancing along to ‘The Best Things In Life Are Free’ while surrounded by a chorus of secretaries before vanishing into his office with a benevolent wave.

Becoming one for the history books, Bert croons the lyrics of the shoe-shuffling song, which seem to endorse a form of interplanetary space socialism: “The moon belongs to everyone, the best things in life are free, the stars belong to everyone, they gleam there for you and me.”

8. Guy Walks Into An Advertising Agency (S3 E6)

8. Guy Walks Into An Advertising Agency (S3 E6)

Written By: Matthew Weiner & Robin Veith Directed By: Lesli Linka Glatter

Besides being bloody brilliant, this episode received acclaim for the perfect execution of Chekhov’s gun trope – a concept that stipulates how every element of a story should contribute to the whole; for instance: if you show a gun in the first act, then in the following act it should be fired.

Only in this darkly comedic episode, the gun is a John Deere ride-on lawnmower operated by a drunken secretary, who has trouble manoeuvring the machine and ends up severing the foot of London account executive Guy MacKendrick before crashing through a blood-splattered glass wall.

Immediately following the freak accident, Don Draper and Joan Holloway consider the fragile nature of life while sitting next to each other in the hospital waiting room. Joan says about Guy: “I bet he felt great when he woke up this morning.” Adding: “But that’s life. One minute you’re on top of the world, the next minute, some secretary is running you over with a lawnmower.”

By this point, Joan understands this better than anyone as she has resigned herself to the fact that her life’s hopes and dreams are now unlikely to ever become a reality, even more so after she learns that her husband failed to receive his promotion at work (the same promotion which enabled her to quit her job).

Amid the wreckage of the episode’s disasters, Peggy Olson’s sincere exchange with Joan turns out to be the highlight of the hour as she thanks the departing secretary for all of her advice and inspiration throughout their time together in the workplace, to which Joan breaks down crying.

7. Signal 30 (S5 E5)

7. Signal 30 (S5 E5)

Written By: Matthew Weiner & Frank Pierson Directed By: John Slattery

Signal 30 had the immeasurably difficult task of trying to make viewers look beyond all of Pete Campbell’s undesirable qualities, and instead feel sympathy for the troubled account man, who is revealed to be a quivering bundle of catastrophes and inadequacies.

Beneath his bravado of supercilious smirks and sycophantic sniggers, Pete’s picture-perfect life is falling apart faster than an unstable Jenga tower, with Don Draper leaning forward to take another block out when he fixes the leaking faucet at the Campbell residence, sans shirt.

The shame of the situation sends Pete on a downward spiral towards his lowest emotional point ever as his resentment deepens for his glass-half-full counterpart, Ken Cosgrove, who has been moonlighting as a science-fiction author, publishing stories under the pseudonym of Ben Hargrove.

With the cracks beginning to show, Pete takes a break from his usual duties to attend a driver’s education course, but faces another knockback when he discovers a new student, Hanson (enviably nicknamed “handsome”), has attracted the attention of the girl that he previously tried to seduce.

By this time, it’s safe to say that Pete has taken a beating, both emotionally and physically at the hands of Lane Pryce, who pummels his colleague square in the face (as per the Marquess of Queensberry rules) during a mad-capped fist fight in the conference room.

Feeling down on his luck, a thoroughly broken Pete despairs at the day’s events with Don in the elevator. Close to tears, he privately proclaims: “I have nothing, Don” – a heartbreakingly sad statement, not because it’s true, but because Pete discloses that he is incapable of appreciating his privileged life.

6. In Care Of (S6 E13)

6. In Care Of (S6 E13)

Written By: Matthew Weiner & Carly Wray Directed By: Matthew Weiner

In parallel to Pete Campbell’s breakdown, Don Draper’s personal and professional life is also on the verge of imploding around him in the season six finale as he tries to overcome the fundamental realities of his present existence by revisiting his forcibly forgotten past.

Time and time again, Don, the biggest ad man in the business, delivers his word-perfect signature pitches to an open-mouthed audience of fictional clients (companies like Lucky Strike, Dow Chemical and Jaguar), as well as real-world clients (the TV viewers).

However after spending a lifetime spinning stories to his advantage, Don decides to change tack in the middle of his Hershey’s pitch, which started out with a sentimental story about how he used to receive one of their candy bars as a reward for mowing the lawn.

“I grew up in Pennsylvania, in a whorehouse,” Don continued, breaking down over his horrifying childhood, voice nearly cracking. “Closest I got to feeling wanted was from a girl who made me go through her john’s pockets. If I collected more than a dollar, she bought me a Hershey bar.”

It may have been a spectacularly bad time to launch into a confessional, but it was an imperative moment for the award-winning star of Sterling Cooper who, up until now, had been portrayed as a serial womanizer, carrying around a briefcase full of secrets and lies.

The episode closes with a moment of reckoning for Don as he finally comes to terms with his troubling past and comes clean with the person who matters the most: his eldest daughter, Sally Draper. In doing so, he shows her the house where he grew up, situated in a dilapidated neighbourhood in Pennsylvania.

5. The Other Woman (S5 E11)

5. The Other Woman (S5 E11).png

Written By: Matthew Weiner & Semi Chellas Directed By: Phil Abraham

This episode is a brutal reminder of the gender inequality of office politics, as three intelligent, ambitious ladies are objectified on some level as “something beautiful you can truly own”, to quote Michael Ginsberg’s Jaguar tagline, where he portrayed the luxury vehicle as an unattainable woman.

Following the parallel dilemmas of Joan Holloway and Peggy Olson, specifically whether they should accept or reject their respective offers, we learn that happiness comes at a severe cost, which may not always be worth the sacrifice of a person’s integrity and values.

Regrettably, no one knows this better than Joan who trades a one-night stand with Jaguar executive Herb Rennet for a 5% stake in the company and promotion to partnership, as a consequence of the smarmy salesman’s archaic demands.

Despite the appalling prospect, the majority of her colleagues resign to the fact that she will be offering her sordid services to the dealer manager, aside from Don Draper who – rather ironically – is the only person in the office to oppose the indecent proposal based on principle.

Elsewhere, Megan Calvet’s flourishing acting career begins to create tension in her marriage to Don, especially when she receives a callback for ‘Little Murders’, with three months of rehearsals scheduled to take place in Boston, Massachusetts.

Don faces further conflict in his working relationship with Peggy as she resigns from the company, citing unfair conditions at work, following a fateful meeting with Ted Chaough (who works at the rival firm Cutler, Gleason, and Chaough), from which Don learns that there are some things that money cannot buy.

4. Smoke Gets In Your Eyes (S1 E1)

4. Smoke Gets In Your Eyes (S1 E1)

Written By: Matthew Weiner Directed By: Alan Taylor

Smoke Gets in Your Eyes is the first episode of the first season of Mad Men, which originally aired on July 19, 2007 – and over a decade later, it deservedly earns a spot in our top ten countdown because it set the bar high right from its opening scene.

Establishing the era with a subtle elegance that is rarely achieved, we are introduced to the protagonist of the period drama, who is sat alone at a booth in a smoke-filled restaurant, and it quickly becomes apparent that this is an age where everyone is selling something and nothing is quite as it seems.

The first hour of the show is impeccably structured; we follow the duplicitous life of Don Draper, who works in the bustling city of Manhattan and lives in the suburban village of Ossining, but his heart resides elsewhere – and at this point, we’re not even sure that he knows where that is.

It’s something of a day in the life crusade – where we’re dropped into somebody else’s world and invited to draw our own conclusions from it – tracking the movements of (apparent bachelor) Don, as he romances Midge Daniels, a footloose art illustrator with a crew of bohemian pals.

Later, the Dick Tracy-cut character joins Roger Sterling for a business meeting with department store heiress Rachel Mencken, who airs her grievances over the agency’s suggestions, which ultimately causes Don to storm out of the room, saying: “I won’t let a woman talk to me like this.”

By the revelatory final moments of the episode, our eyes have been opened to the soullessness of advertising, which is all about selling the dream but not necessarily living it, as Don returns home to his beautiful wife and children to whom he has been unfaithful.

3. The Wheel (S1 E13)

3. The Wheel (S1 E13).jpg

Written By: Matthew Weiner & Robin Veith Directed By: Matthew Weiner

On the goosebump-inducing scale, the final episode of the first season of Mad Men scores a ten every time, largely due to the fact that it features one of the most memorable moments of the entire series, by way of Don Draper’s brilliant campaign presentation for Kodak.

Set within a darkened conference room, Don uses his own memories to sell their slide projector as a portable time machine, with images from the Draper family album streaming on the screen to reinforce the message behind his inspiring speech, which pours out from his deeply wounded core.

“Teddy told me that in Greek, ‘nostalgia’ literally means ‘the pain from an old wound,’” he explains to the 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.”

With that thought echoing inside him, Don races home to his family, only to find an empty house; he sits on the staircase, listening to the silence and feeling his loneliness, which only emphasises the reason why nostalgia is such a powerful force: you can’t go back to that place once it’s gone.

Other notable moments in the season one finale include a newly promoted Peggy Olson giving birth (not even having known she was pregnant), Betty Draper’s private revelation about her husband, and the tragic news that Don’s estranged brother has committed suicide.

2. Shut The Door. Have A Seat (S3 E13)

2. Shut The Door. Have A Seat (S3 E13)

Written By: Matthew Weiner & Erin Levy Directed By: Matthew Weiner

As far as season finales go, the conclusion of season three was a full-on fist-pumper of an episode, which proved itself to be a bizarrely upbeat change of pace for a series that has developed a reputation for being a dark and brooding drama.

Essentially, this episode is a thrilling caper movie about a gang of thieves (The Sterling Cooper crew) who hatch a harebrained scheme to escape their British rule and launch their own advertising agency, stealing all pertinent client records in the process.

“They’re going to be up against the wall, and they’re going to have to gather all the players together. Everybody has to have a special skill, a special reason for being there,” Don Draper explains in his humbling attempt at assembling the greatest band of misfits the ad game has ever known.

Chiefly Peggy Olson, to whom he owes a gargantuan apology as a result of making her feel unimportant. He tells his former mousy, servile secretary that he understands, and appreciates her – which is a message that she has been longing to hear because she, just like Don, has lost a lot along the way.

Warm fuzzies aside, the season closer actually has a very bittersweet edge to it because while Don is mobilizing his work family, his actual family is falling apart since his wife, Betty, finally amassed enough evidence to confront him over his lies.

1. The Suitcase (S4 E7)

1. The Suitcase (S4 E7).jpg

Written By: Matthew Weiner Directed By: Jennifer Getzinger

Don Draper and Peggy Olson’s dynamic relationship developed over several seasons, culminating in one long, exhausting, revelatory all-nighter that takes the boss-employee duo from the office to the diner, the bar and back to the office again, slap-bang in the middle of the fourth season.

Blending fan-approved character comedy with raw unbridled emotion, ‘The Suitcase’ plays out like a cathartic movie, whereby the lead characters discover that they’re the only two people who will ever truly understand one another, during a late-night bonding shift.

The episode opens at the end of a workday, when Peggy is supposed to be clocking out but ends up clocking in after making the fatal mistake of stopping by Don’s office, where she ends up being drawn into a brainstorming session for the upcoming Samsonite campaign.

Laying their cards out on the table, Don and Peggy’s conflict reaches an almighty climax, as they viciously fight before they start to offload their troubled baggage – which includes: Peggy speaking about her baby for the first time in years and Don breaking down over Anna Draper’s death.

In a remarkable evolution, the two recognise each other as equals for the first time since the series started, with Don’s deep gratitude reflected through his body language as he grasps Peggy’s hand in a mirror image of their first awkward interaction, marking just how far they have come.

And at the end, Peggy leaves the door open.

Which episode of Mad Men is your favourite?

Film Signature

Twitter: @AdeleAnkers

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