When Mad Men went on a year-long break at the behest of TV channel/merciless cash-cow milkers AMC, I was left confronted with two choices; watch the entire series again or get a life. For once, I went for the option that involved marginally less chain-smoking and tore through every episode. Before the beginning of the end kicks off this Sunday, here’s my tribute to Mad Men’s slow burn of slammed doors, 9am straight vodkas and all the existential layers beneath as I highlight the most gripping episodes to date.

(To the spoiler-adverse: run while you can. To everyone else: shut the door, have a seat).

10. ‘Guy Walks Into an Advertising Agency’ (Season 3, Episode 6).

4th of July. A day of fireworks, apple pie and in this case, amputation, dawns on Madison Avenue – and is there a more apt time for Sterling Cooper to scramble around the arrival of their British bosses than American Independence day? Fear not, patriots, for as the debauchery following PPL’s reshuffle of the agency and Joan’s leaving announcement spirals, budding new Operations Manager Guy MacKendrick gets a foot mauled by a lawnmower in one of Mad Men’s best bouts of black humour.

Outside of that horrifying/hilarious sequence, the foot-related jibes are relentless (Kinsey: He might lose the foot, Roger: Just when he got it in the door, ‘The doctors say he’ll never.. golf again’, the episode title itself), adding bite to an episode that thrives off bristling cultural tensions and stilted small-talk.

PPL’s reshuffle spreads fears of change around the office, inspiring a servility typical of Pete and Harry and growing concern from Roger towards his own displacement. The realisation of this theme comes most poignantly through Joan, who resigned under the assumption her surgeon husband would be promoted only for him to end up with no job at all. Made all the more sombre by her level-headed approach to lawnmower-gate, Joan leaves Sterling Cooper to a world of increasing instability just in time for the blood to dry.

9. ‘Shoot’ (Season 1, Episode 9).

Tedium by nature can be difficult ground to explore. Though office politics are driven by a dynamic web of forces – be it shifting allegiances, uphill struggles for recognition or the threat of taking a lawnmower to the foot – the suburbs are glazed in stasis. Dreams become things to get you through the day, or your next cigarette, before you wake up too numb to rattle the cage you’re in. Mad Men probes how the expectations and constraints of middle America can break a person through various characters, though rarely bleaker than with Betty.

Groomed to please by a wealthy family then shoved out to play house in Ossining, the ex-model is given the chance to live for herself again through an offer to star in a Coca-Cola campaign. However, the cruel reality emerges that Betty’s modelling job is completely contingent on Don jumping ship to work for McCann (Coca-Cola’s ad reps), highlighting how powerless she is even in ‘freedom’, and so she returns to her squeaky-clean prison.

The final scene of Betty shooting at her neighbour’s pigeons (but not quite hitting them) is one of my favourite bits of symbolism in the show. Equally funny and tragic, Betty plays at being maternal yet is more miserable and resentful than ever before. Though those two traits increasingly come to define the character, ‘Shoot’ marks Betty at her most sympathetic and at her breaking point.

8. ‘Shut the Door, Have a Seat’ (Season 3, Episode 13).

In ‘The Summer Man’, Henry Francis advises Betty that ‘there’s no such thing as a fresh start’. Lives may continue as long as the same people live them but our environments can always change – regardless of whether we like it – so why not warp the world around us to keep afloat?

There’s no character who understands reinvention better than Don and this episode is a perfect showcase of his ingenuity. As the sale of Sterling Cooper and PPL to McCann looms, Roger and Bert accept they’re anchored to a sinking ship. Whilst Don can no longer swim against the tide in his crumbling marriage to Betty, he can pull Sterling Cooper out of the water, and that’s exactly what happens when he asks Lane to sever their contracts so the agency can start anew.

The episode’s tone is remarkably close to a heist film’s caper for an hour featuring no gunshots, yet assembling the partners in crime requires some personal acknowledgements on Don’s end. Roger’s comment that Don ‘doesn’t value relationships’ stings with truth as Don gives Pete the respect he pines for and admits that he – and not just the firm – needs Peggy, who won’t fall in line with a click of his fingers. New beginnings with the same old people might seem hollow but the promise, at least, is always thrilling.

7. ‘Meditations in an Emergency’ (Season 2, Episode 13).

Mad Men’s incorporation of historical events ranges from a look at their overt impact (Martin Luther-King’s death in ‘The Flood’) to use as thematic props (The Richard Speck murders and race riots in the horror-styled ‘Mystery Date’), but none are examined with the sky-high stakes of this episode.

Set as the Cuban Missile Crisis reaches a fever pitch, doom spreads from the city to the suburbs as the threat of apocalypse forces characters to confront their feelings and make drastic decisions. After a season of sexual repression and building frustration towards Don, Betty has a fling of her own at a bar, whilst Don himself quashes a power play from Duck following Sterling Cooper’s merger with PPL.

However, the episode’s most devastating scene comes when Pete confesses his longing for Peggy only to be rebuked by the reveal that she gave up his child. It’s a brutal conversation that calls upon two seasons worth of history – shared and secret – from Peggy’s pervading Catholic guilt to Pete’s inability to conceive with his own wife and the hollowness they recognise in each other as work rules their lives. Above all, it’s a rare admission of truth between two guarded characters whose hands are forced by the end of the world and stands as the show’s most genius use of historical context to date.

6. ‘Signal 30’ (Season 5, Episode 5).

Let’s get the obvious out of the way – any episode that features Pete getting smacked silly as Roger all but breaks out the popcorn was always going to rank amongst the show’s best. Whilst it’s absolutely glorious to see Lane refer to Pete as a ‘grimy little pimp’ before mangling the weasel’s face, it helps that the rest of ‘Signal 30’ is a fascinating study of emasculation.

Lane bags a meeting with a Jaguar rep after straining to enjoy England’s 1966 World Cup victory, only to find himself incapable of closing the deal as the rep scurries to Roger and co. for some whorehouse fun that the straight-laced Lane can’t provide. After Pete challenges his professional and sexual competence, the infamous curb-stomp ensues before Lane stumbles at finding solace in Joan. It’s a rejection, but a tender and respectful one; two words that have no place in Pete’s story.

The only adult in a driving class, Pete is delirious with pride from flirting with a teenage classmate and by fixing a leaking faucet at home, both of which sour as the girl’s attention moves to a younger guy and the faucet bursts for Don to effortlessly repair. By the end of the episode, Pete’s sneer of ‘I have everything’ after his tryst in the brothel crumbles into a post-beatdown blubber of ‘I have nothing’, excellently performed as Vincent Kartheiser reveals the boy in the suit of a businessman.

5. ‘The Gypsy and The Hobo’ (Season 3, Episode 11).

There’s a curious admission near the start of the episode when Don tells Roger that he’s eaten horse meat. It’s a small nugget of information, more characteristic of the farm boy Dick Whitman, that bleeds into the Don Draper persona. Nevertheless, Don is in control. Little does he know that this constructed poise is about to completely collapse as Betty knows he is not who he says he is.

Jon Hamm’s performance in the Don/Betty confrontation is one of the best across the entire series; realising that this time he’s unable to force or persuade Betty that she’s mistaken, Don’s face falls to a look filled with dread beyond a simple ‘oh shit’. It’s the look of someone whose most distressing fears and nightmares are coming to life with no means of escape, for as much as this is a confrontation between Don and Betty, it is part of the ongoing war between Don and Dick Whitman.

Season 3’s main undercurrent is one of changing times – from generational rifts to corporate restructure – but the rekindling and ruin of the Draper marriage is the most painful realisation of this theme. Betty can’t help but sympathize as Don unravels to unveil a man psychologically fraught beyond imagination, but it also exposes that their marriage was predicated on a lie so big it dwarfs Don’s everyday infidelities. Later, the two take Sally and Bobby trick-or-treating and after a man comments on the kids’ costumes, he turns to Don with a question at the core of the whole series;

‘Oh. And who are you supposed to be?’

4. ‘Waterloo’ (Season 7, Episode 7).

The Moon Landings of 1969 represent a huge triumph for the human race, an event where mankind looked uncertainty in the face and blasted into uncharted territory. So it seems fitting, and almost generous, for Ayn Rand champion Bert Cooper to live just long enough to applaud a grand achievement of opportunity before a peaceful end.

The impacts of Cooper’s death and the Moon Landings ripple throughout the episode, most notably with Roger, whose final conversation with Cooper (‘You’re not a leader’) inspires a long-absent assertiveness as he sells 51% of the firm to McCann whilst retaining autonomy. Another mentee who comes out roaring is Peggy, whose knock-out Burger Chef pitch marks the end of a severe burnout and cements Don’s admiration of his old protégé. Elisabeth Moss is fantastic throughout, putting Peggy in total command of the pitch whilst her goodbye to Julio reminds us how giving up her child all those years ago still haunts the margins of Peggy’s mind.

Don however has a much more troublesome time. After his marriage to Megan finally caves in – with a scene that devastates because of how little is said – Cooper’s death rips open a power vacuum in favour of Cutler’s attempt to oust him from the firm. Don manages to navigate through thanks to Roger’s deal, dragging Ted Chaough back to hell to save himself. With the partners now rich beyond their wildest dreams, all seems calm until Don hallucinates a rendition of The Best Things in Life are Free courtesy of Bert Cooper in a whimsical, absurd scene that is above all a chilling omen.

3. ‘The Suitcase’ (Season 4, Episode 7).

Bottle episodes, whilst forced by a network due to budget reasons, can often be among a show’s best. By trimming some colourful side characters and more extravagant locations, a script is then allowed to examine one particular relationship or theme with laser-focus. Knowing someone – really knowing someone – means they can comfort and hurt you like no other, and both of those are wrung out raw during Don and Peggy’s all-nighter.

For all of Don Draper’s sexual acrobatics there are precisely two relationships that really pierce the man’s psyche – both of which are strictly platonic. Anna Draper’s inevitable death looms over Don in this episode as he spends the night dodging phone calls about her worsening health, instead burying the issue with whiskey and berating Peggy, whose work has such a gravitational pull that she spends her birthday in the office, boiling with frustration towards Don.

If John Hamm and Elisabeth Moss have been better than in this episode, it’s not by much. The two cycle between passive-aggressive barbs, shredding each other to pieces, lamenting the past and consoling each other with the thorough intimacy of people who understand each other inside and out. The morning after, Don takes Peggy’s hand in gratitude following Anna’s death in a nice reversal of Peggy’s come-on to Don in the pilot. Without a formal introduction, Peggy has met Dick Whitman.

2. ‘The Other Woman’ (Season 5, Episode 11).

Sometimes, the inevitable can shock more than a surprise. Pry Pandora’s box open just a tad and sooner or later all the world’s sins will come spilling out. Early in the episode, a rep from Jaguar poses an ultimatum over dinner: a night with Joan, or you won’t win the account. The person on the receiving end of this is, of course, Pete, who slithers back to Joan with the news only to be laughed off. However, the further the dilemma writhes around the office, the more mortifying life is breathed into it to the point where Joan demands a partnership for the act.

From this point on, the episode becomes horrifying. In a clever bit of editing, we’re given a potential life raft as Don arrives at Joan’s apartment to talk her out of it – only to later reveal that this happened after she already slept with him. As unnerving as the situation is, Joan is just about pragmatic enough for her to believably consent and Christina Hendricks is magnificent in selling Joan’s desperation for financial security as a single mother and disgust for everyone involved in the situation – most damningly, herself.

This episode is so huge that I haven’t even got to Peggy. After a season-long creative breakdown and one too many derisive onslaughts from Don, Peggy finally acts on her frustration and jumps ship to Cutler, Gleason and Chaough. The scene where Peggy tells Don she’s leaving is stunningly acted, as Don starts off casually condescending, then seething, then horrified that she’s serious before the two barely manage to keep it together.

Whilst ‘The Other Woman’ may be heavy-handed in conveying its theme (the objectification of women), this is such a monumental episode on both a plot and a character level that it’s hard not to consider it a masterpiece. The question is – what’s better than this?

…

1. ‘Far Away Places’ (Season 5, Episode 6).

Mad Men’s fifth season remains my favourite to date. From the deepening generational rifts to the fevered sex dreams and ominous death symbolism, there’s a distinct aura that everything is spinning out of control. Nowhere is this more visceral than in ‘Far Away Places’ – one of the show’s most experimental episodes – where Peggy, Don and Roger dive down the rabbit hole in three intersecting vignettes of escapism over the course of one day.

Having burned several professional and personal bridges in record time, Peggy ducks out of work early in Draper-like fashion, because there’s no stress relief like smoking weed and wanking a stranger off in the cinema. It’s here that the episode does something remarkable; after Peggy wakes up in complete darkness, the passage of time pulls back to the start of that morning, now from Roger’s perspective. The episode already feels trippy – and this is before Roger takes acid.

From the visuals to the dialogue, the tripping sequences are brilliant – vibrant and fragmented without feeling forced – yet it’s the calm after the storm that hits the hardest as Roger and Jane have an unflinching discussion about their failing marriage. John Slattery and Peyton List turn in series-best performances in the bitter-sweet fallout, augmented by dialogue that evokes a whole spectrum of complex emotions at play (Jane: There was a kiss but I stopped it. Then I was mad at you because you didn’t appreciate it, even though you didn’t know about it.)

Though Roger ends the episode with more clarity than ever before, the most harrowing trip belongs to Don and Megan. Husband and wife, boss and employee and authority and freedom, their dynamic is fraught with conflicting challenges and a fight turns especially ugly when Don abandons Megan in a restaurant car park. What follows is perhaps the most distressing scene in the entire series when Don’s frantic search for Megan leads him back to their apartment and the argument erupts into a physical and emotional outburst. And so Peggy, Roger, Don and Megan return to work the next day, profoundly shaken by their experiences in Mad Men’s most structurally daring episode to date.

Well, that’s it. Despite how difficult it was to narrow down the best episodes of this excellent show to a mere 10, I have no doubt that the upcoming final seven will trouble any definitive list and have thoroughly enjoyed revisiting some of my favourite TV episodes of all-time. What did you think?