The five-year anniversary of Mad Men: reflections and recommendations

This year (the 18th of May) marked five years since the series finale of Mad Men. In the intervening years, I’ve seen many other TV shows, but none that I’ve thought of as often or that have affected me in quite the same way. 

In case you missed it, Mad Men is set in the microcosm of advertising in 1960s Manhattan, and follows ad-extraordinaire Don Draper, as he seeks to escape his true identity in the futile search for connection and a sense of belonging. The series reflects on an era that is rife with racial tensions and that just pre-dates the rise of second wave feminism; a time of rapid social, cultural, and political change, and Don Draper is a meditation on each of these aspects.

So, in honour of the seven seasons that creator Matt Weiner imparted, here’s seven of the must-see episodes (warning: spoilers ahead).

The Wheel (Season One, Episode Thirteen)

The Wheel features perhaps the finest salesman moment of the whole series, as Don pitches an idea to Kodak, who are struggling to sell an old-fashioned slide projector. The ticket, he tells them, is not the glimmering lure of technology, but something more powerful: nostalgia. A slideshow of photographs appears on the boardroom screen, as Don guide the room on a tour of a life that doesn’t really belong to him, and a family whom he barely knows. The man who only ever goes in one direction – forward – brands nostalgia as ‘a twinge in your heart, far more powerful than memory alone.’ The device that Kodak are selling is powerful, Don says, because ‘it takes us to a place where we ache to go again,’ a place ‘where we know we are loved.’ 

The Gold Violin (Season Two, Episode Seven)

The Gold Violin opens with Don purchasing a shiny new Cadillac, and it ends with Betty, Don’s first wife, sitting in silence beside her husband and suddenly vomiting, ruining her dress and the car. What transpires in between these two moments gets to the heart of Don’s weaknesses – as a businessman, but particularly as a husband, as Betty learns of Don’s affair with his client of the moment, Bobbie Barrett. It’s a critical moment that sets forth the undoing of Don and Betty’s ill-fated marriage. 

The Gypsy and the Hobo (Season Three, Episode Eleven)

Season 2 has an another, arguably more memorable episode featuring a secretary and a rogue lawnmower (I’ll say no more), but there’s a pivotal scene in The Gypsy and the Hobo between Don and Betty that, even years later, cements it in my mind as one of the greatest episodes of the series. At least once a season, Mad Men will strip away its layers and return to the idea at its core: a man plagued by a past he can’t escape. This episode encapsulates that perfectly, as Betty unexpectedly confronts Don about the box of memories – letters, photographs, war memorabilia – that she’s discovered in his office. Instantly, the ever-assured Draper shell dissipates to leave Dick Whitman, standing naked and afraid before his wife, the one person who should know him best. Afterwards, when Don and Betty take the kids trick-or-treating their neighbour asks, 'Who are you supposed to be?' Neither of them has an answer.

The Suitcase (Season Four, Episode Seven) 

There’s an argument to be made that is the best episode of Mad Men (and one of the best episodes in television history, period). At the very least, it’s the one that encapsulates the sum of the show’s greatest preoccupations and ideas within the confines of a singular storyline, as Don and Peggy, his protégé, pull an all-nighter, from office to diner to bar to office again. It’s if they’re the only two people awake in Manhattan, and in this solitude Peggy discovers that she's exactly like Don. It’s a reminder that, particularly for Don, this might be the closest thing either of them get to understanding another person, and to being understood in return.

The Other Woman (Season Five, Episode Eleven)

The Other Woman is remarkable mainly for its analysis of the development of one of show’s leading female characters, Joan Holloway. Mad Men's presentation of Joan has always walked a fine line: she’s aware of the sexual power she has, and of the benefits she’s received because of the way she looks (one of many similarities between her and Don, though of course this sort of power functions very differently for a man). These complexities in her character are articulated more literally in this episode, when a highfalutin prospective client informs the company that they’ll only have his vote in exchange for sex with Joan. Joan, once she’s informed, calls it out for what it is: prostitution. Pete Campbell, on the other hand, prefers to think of it as 'business at a very high level.' Ultimately, they get the account, and it’s only when a horrified Don sees that Joan has traded in her office manager status for a partnership that he realises she followed through on the deal. It’s an episode that stirred some controversy, but I’d argue it’s critical, both for its examination of Joan’s character and the repercussions of her decisions that echo for seasons to come, and also for what it reveals about the moral qualms (or lack thereof) of the men at the company. 

In Care Of (Season Six, Episode Thirteen)

In Care Of features a rare personal breakthrough for Don following a harrowing few months (or years, or decades, depending on how you look at things). Unfortunately, this breakthrough happens while he's drunkenly presenting a pitch to an important prospective client. His life in ruins, Don hits the road with his kids and stops in Pennsylvania to show them the whorehouse where he grew up; unable (and perhaps ultimately unwilling) to escape the past that continues to invade his present. In a striking final shot, Don’s daughter, Sally, looks up at her father with a raised brow, realising she doesn’t know him at all. They stand there by the side of the road together, in silence, as Judy Collins’s ‘Both Sides Now’ closes the scene.

The Strategy (Season Seven, Episode Six)

There’s something about The Strategy that feels like its marking the closing of a chapter on the Mad Men of old, as in its seventh and final season, the show grapples with how to handle well-worn dynamics between characters that are, both professionally and personally, on the precipice of great change. Indeed, the episode creates an air of nostalgia, as it features some of the show’s longstanding tropes: Pete Campbell behaving like a brat, Roger Sterling delivering wry one-liners, Peggy and Don bickering in the search for the perfect campaign (à la season four’s The Suitcase)and Don and Megan (his second wife) perfecting the art of performative happiness in a marriage that’s heading towards impending doom. But crucially, The Strategy also reminds the audience that things are not as they once were: Sterling Cooper & Partners are about to lose a prized account, and in a reversal of roles, it’s Peggy exerting her authority over Don, and Megan who appears to be pulling away from the confines of her marriage, not the other way around. These hard-bitten truths are softened by some of the more sentimental moments of the season, like Don and Peggy reaching a harmonious accord (as they always do) and slow dancing to Frank Sinatra’s 'My Way'. Then there's Pete, Don, and Peggy sitting down to dinner at a fast food joint as, even if only briefly, we’re invited to remember these characters, who are first and foremost colleagues, in the way that we’d always like to: as a makeshift family. 

Tagged in Television, Culture, What messes with your head