The Top Ten Mad Men Episodes

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Every May I get memories on Facebook about the series finale of Mad Men. One of the first blog posts I ever wrote on this site was about that series finale and other notable final episodes. So, subsequently every year around this time I get a hankering to check in on the adventures of Don Draper and the gang.

I’m sorry to say, I’m sad to report that I simply don’t have the chops to take any deep dives regarding this magnificent show and it’s underlying themes. All I know is that every time I watch any episode I come away basically slack-jawed. There is such a depth to this show; you feel there is a massive significance in virtually every scene although the show is not as heavy-handed as all that and is almost equal parts pure entertainment. You really do get so much from this show.

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But if you’ve seen every episode, which ones do you watch when you want to revisit the show? Maybe you have a favourite season. Me, what I’ve done is watch a season’s finale and then watch the next season’s premiere; I like that feeling of viewing the immensity of the end of a season and then watching immediately how they picked up the action. When the show was on the air, there was usually months between seasons.

One year, for something different, I Googled “Top Ten Mad Men Episodes”. What I got was multiple lists from multiple sites; Top Ten, Top 30, All 90 Ranked… I got to wondering which episodes made all of the lists; was there a group of episodes that were unanimously acclaimed as the best? What I found was that there was indeed a handful of episodes that showed up on most lists although it was fun, too, to find the odd site with a list that seemed to favour lesser-known episodes. Once I had perused several of these lists, I came up with a complicated algorithm – as I often do in my spare time just for kicks – to assign values to the episodes that regularly made these lists. The result was what I’ll be so bold as to declare The Absolute Ten Best Episodes of Mad Men. I’ve avoided the grandiose final episode and any two-parters as these episodes already have a built-in significance. And while your favourites – and mine – may not make this list, the thing that makes the list neat and fairly conclusive is that these ten frequently appear in the upper reaches of any ranking of the show’s greatest episodes so it stands to reason that these are the ten that are considered by many to be the finest achievements of a show that experienced many. So, shut the door, have a seat and let’s break it down. We’ll start at #10 and work our way towards the “best Mad Men episode ever”.


10. Shoot (Episode 1.9 Sept 13, 2007) — Don (Jon Hamm) and Betty Draper (January Jones) are seeing a show on Broadway when Don is approached by Jim Hobart from rival agency McCann Erickson. Hobart offers Don the world if he will join his company. “It’s an overture”, says Hobart. When Hobart is alone with Betty, he offers her a modeling job. This causes Betty to remember her days as a model before she married Don and she relates to her therapist that she stopped modeling when she met Don. Soon after, they started dating, followed quickly by marriage and motherhood. She seems to wonder where her life went. Don “allows” Betty to go to work selling Coca-Cola for Hobart’s agency. When Don turns Hobart’s job offer down, it’s clear that McCann won’t need Betty any longer. This makes her sad but Don cheers her by saying that her being an excellent mother is the most important job she could have. Soon after, Betty takes to mothering with a fervour. A neighbour who has trained pigeons has threatened to harm the Drapers’ dog if he goes after his birds, upsetting the Draper children. The episode closes with Bobby Helms’ “My Special Angel” and the iconic image of Betty, smoke dangling from her red lips, shooting at the pigeons with a BB gun. Personal side notes: January Jones must not have been a smoker in real life. Her hands don’t seem natural when she does it, her fingers too rigid and splayed, especially when compared to John Slattery’s Roger Sterling, for example. The actor who plays Betty’s therapist is Andy Umberger who has a significant role in the video game L.A. Noire, a game that stars Mad Men‘s Aaron Staton as Det. Cole Phelps. Lastly, when some of the boys in the office score a victory, they are congratulated by Bert Cooper (Robert Morse) and Roger, who says “I didn’t think you had it in you. And I mean that”

9. The Jet Set (Episode 2.11 Oct 12, 2008) — Roger Sterling is looking to get a divorce but it will likely cost him so much as to put the solvency of the agency in question; and disgruntled ex-employee Duck Phillips may use this knowledge to broker a takeover. Don and Pete Campbell (Vincent Kartheiser) are in Los Angeles on business but Don takes off to Palm Springs with a young dish who travels with a group of wealthy wanderers – the jet set. Their lavish lifestyle looks good but something seems off; the “glass is cracked”. When the young girl tries to coax Don to travel on with the group, he turns her down. Instead, he calls someone who knows him as “Dick Whitman”; this is a significant moment in the context of the show. This inscrutable episode employs well Johnny Mathis’ version of one of the saddest songs I’ve ever heard, Irving Berlin’s “What’ll I Do?”.

8. The Crash (Episode 6.8 May 19, 2013) — Don is reeling from the rupture of his relationship with Mrs. Sylvia Rosen (Linda Cardellini) and has flashbacks of a time when he had a chest cold as a child back at the whorehouse. Sylvia is concerned by Don’s reckless behaviour thinking it will alert her husband. “I’m afraid of you”, she tells him. At the office, the employees get a “vitamin shot” and go bonkers. The drug causes Don to work non-stop for three days but his brainstorming is more aimed at Sylvia than at Chevy. Interestingly, there’s an amateur mind-reader at the office who asks Don to think of a question. Later, she tells him correctly that his question was “does someone love me?”. Sergio Mendes and Brasil ’66’s “Goin’ Out of My Head” is used well.

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Linda Cardellini as Mrs. Sylvia Rosen.

7. Commissions and Fees (Episode 5.12 June 3, 2012) — Sterling Cooper Draper Pryce has successfully landed the Jaguar account but the venerable car company is suggesting a different pay structure; fees as opposed to commissions. This requires a perusal of the books which reveals a cheque signed by Don and payable to Lane Pryce (Jared Harris). In a compelling scene, Don confronts Lane saying he didn’t sign the cheque and Lane admits to embezzling money from the firm. “I’m gonna need your resignation”, Don tells Lane who is broken, bitter and disgraced. The meeting with Lane prompts Don to want SCDP to forge ahead and get bigger and better clients. He pushes Roger to get them a meeting with Dow Chemical and Don pitches them vigorously, browbeating them soundly, challenging them to reach for higher heights, heights SCDP can help them achieve. Lane, meanwhile, goes home to his wife who surprises him with a new Jaguar which just makes Lane more desolate. He gets out of bed in the middle of night, goes to the office and hangs himself. This was staggering when first viewed as we who watched the show regularly did not see this coming. The scene depicting Joan discovering something amiss in Lane’s office is harrowing and the partners having to deal with a corpse was not something seen on the show before. Don doesn’t tell what he knows about Lane’s money troubles and we fade out to the sounds of the Lovin’ Spoonful’s “Butchie’s Tune”.

6. The Strategy (Episode 7.6 May 18, 2014) — Pete and his current squeeze, Bonnie, fly into Manhattan from the Coast to work on Burger Chef with Peggy and her team. Pete and others at the office praise Peggy’s work and Pete pays her a backhanded compliment; She’s as good as any woman in this business!”. Although Don has been keeping it low key at the office lately due to his latest round of transgressions, Pete pushes to have Don involved to the extent that he suggests that it should be Don that presents the pitch to Burger Chef. Peggy bristles at this. She is finally emerging from Don’s shadow and feels she doesn’t need his help. When Don casually mentions that Peggy’s idea for the presentation could take another direction, she second guesses herself and becomes angry. She feels that Don is saying the work is no good and she tells him as much. In another example of Don and Peg digging in to work, the two huddle together to figure out a new way to make the pitch. Interestingly, Don is humbled by this point and is acting somewhat subservient. Wife Megan visits from LA and he – more than her – seems to relish their reunion. Don is gentle with Megan and self-effacing at the office. The significance of this episode is once again derived from the dynamic between Don and Peggy, lending credence to the idea – discussed later in this article – that Mad Men is about their relationship. After a bit of sparring, Peggy asks Don, as a protegé is apt to do, for help; “Show me how you think”. The first step, Don says sheepishly, is to “abuse the people who’s help I need” and they share a smile. The two become personal, Peggy concerned that life is passing her by – all she has is the work she is becoming excellent at. Don reassures her on this point – “I worry about a lot of things. But I don’t worry about you” – and opens up about his own worries, similar, actually, to Peggy’s. They both lament the fact that they have no family like the one they wanted to depict in the Burger Chef ad. This leads Peggy to suggest that their hook should be that this restaurant could be considered home and anyone you dine with could be considered family. Frank Sinatra’s “My Way” comes up on the radio and the two dance. If Mad Men is about Don and Peggy, if the show is mostly concerned with the arc of their relationship, then this dance may be the most significant moment on the show. As they dance, Peggy slowly puts her head on Don’s chest. He is so moved and his reaction is so tender that you could ponder at length what feelings lead to her actions and what emotions caused him to make his gentle gesture.

5. The Other Woman (Episode 5.11 May 27, 2012) — The episode that aired previous to #7 on this list, The Other Woman finds SCDP actively courting Jaguar’s point man, Herb Rennet, who crassly makes it plain that the agency landing the account hinges on Rennet getting to spend the night with Joan Harris (Christina Hendricks). This plot point makes this episode difficult to watch. Pete Campbell shows his slimy side by taking Rennet’s suggestion to Joan who seems “amused” but of course shuts the idea down; “You’re talking about prostitution”. Pete makes himself abhorrent by saying to Joan “if you can think of a way to tell the company” that she’s not interested… When Pete tells the other partners that he brought it up with Joan they are aghast, Lane particularly is disgusted. However, the partners discuss potential financial dispensation to Joan if she agrees. The fact that this is even being bandied about is hard to believe. Lane pays Joan the courtesy of telling her to insist on a partnership if she goes through with it. Joan meets with Pete the next day; “Tell them I want a partnership. Not silent”. Don – who had left in disgust when the partners were discussing this – reacts violently when he hears Joan has agreed. He goes to Joan’s apartment to tell her it is not worth it. Don is being noble here and it is a tender moment between he and Joan – but it appears Don may be too late. This whole scenario certainly causes the viewer some discomfort. Later, when all the partners are called into Roger’s office and Joan walks in, Don is upset, realizing what this means. Meanwhile, Peggy has suffered at Don’s hands for the last time and accepts another job. The scene depicting her telling Don she is leaving SCDP is poignant, mentor and protegé sharing a bittersweet moment. Is Don hurt? Just sad? He is certainly dumbfounded. Peggy waits for the elevator looking back at the door of the agency wistfully. But as the Kinks’ “You Really Got Me” kicks up, she smiles and walks away. This episode is significant due to the life-changing decisions the two principal female characters have made.

4. Guy Walks Into an Advertising Agency (Episode 3.6 Sept 20, 2009) — Sterling Cooper are having their Fourth of July holiday wrecked by a surprise visit from their bosses in London, Putnam Powell & Lowe. Bert Cooper speculates that they might be looking to elevate Don to an international position, an idea Don takes to. The English arrive and announce a slight shuffling of personnel that will see Lane moved to Bombay. When Don learns that nothing will change for him he tunes out. Roger doesn’t seem to have a significant role to play and he bristles, wondering if he is too good at what he does; “I’m being punished for making my job look too easy”. Bert placates him; “We took their money. We have to do what they say”. Ken Cosgrove (Aaron Staton) is elated to have landed the John Deere account and to celebrate he drives a lawn tractor into the office, much to everyone’s amazement and delight. This is supposed to be Joan’s last day as her doctor husband is moving up at his job and so the office is taking a break and having a party. A secretary is allowed to drive the tractor around but unfortunately she comes too close to PPL’s point man and cuts his foot off. Chaos ensues. Joan thinks quickly and gets the victim to the hospital. Having the Englishman out of commission – “he’ll never golf again” – means Lane will have to stay in Manhattan. Don goes home and bonds with his new baby and Sally to the tune of Bob Dylan’s “Song to Woody”. Really, not a whole lot heavy happens in this episode but it is no doubt revered because of the lawn tractor accident. Which, actually, is significant as it is totally unexpected; much like Lane’s suicide but with the opposite outcome, black humour. Perhaps audiences at the time were surprised to find such audacious comedy in a show like this but it showed that the writers of Mad Men were capable of magic of all kinds. 

3. Shut the Door, Have a Seat (Episode 3.13 Nov 8, 2009) — Don learns from Conrad Hilton that McCann Erickson is buying PPL and Sterling Cooper along with it; meaning SC will be absorbed/liquidated. Don gets together with Bert and Roger to commiserate. Bert is old and Roger has been feeling on the outs anyways so those two seem resigned to the inevitable. Don and Roger have an interesting exchange; Roger accuses Don of not valuing him and his skill set. Roger says “You’re not good at relationships because you don’t value them” to which Don replies “I value my relationship with you” and he actually says “I was wrong”. The three decide to buy SC themselves and take this idea to Lane who scoffs at it. When Lane, who assumes SC is for sale and not PPL, finds out PPL is indeed for sale and he will be cut adrift, he tells the boys he is with them. How would they like to proceed?

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The fledgling agency steal what they can from Sterling Cooper.

Meanwhile, Betty tells Don to get a lawyer because they are getting divorced. When Don – the philanderer – finds out from Roger (by mistake; “I was going to tell you. No, I wasn’t. I thought you knew”) that Betty has found someone else, the idea floors him. He goes home and gets physical with Betty who bravely stands her ground. In a heartbreaking scene, Don and Betty explain to the kids that Daddy is moving out. Their young son wonders aloud if this is happening because he lost Don’s cufflinks. Back at the office, Don comes up with the idea that Lane, who has power over Sterling Cooper as PPL’s man on the scene, could fire the three men, thus leaving them free to start their own agency. Lane agrees; “Well, gentlemen, I suppose you’re fired”. Roger: “Friday, December 13th, 1963. Four guys shot their own legs off”. Bert, Roger, Don and Lane begin to scheme, to take from the offices what and who they need to start their agency. Don tells Peggy to come aboard and she fumes; “You just assume I’ll do whatever you say. Just follow you”. Don then speaks nicely to her – in another one of the poignant scenes between these two – and Peg is in. No one knows where the paperwork they need to steal is and Roger thinks to call Joan. When Don walks in and sees Joan there he says “Joan. What a good idea”. An interesting Roy Orbison song plays us out. “Shahdaroba” may seem an odd choice but the lyrics do comment on the action; “Shahdaroba means the future is much better than the past…in the future, you will find a love that lasts“. This is such a significant episode due to the obvious fact that this entry finds Sterling, Cooper, Draper and Co. ready to be their own agency. Something else I noticed is that this episode features some strong women; Betty doesn’t back down when Don manhandles her, Peggy talks smack to Don when she feels mistreated, making him correct himself and Joan, it is agreed by all, is indispensable and has skills the agency simply cannot do without. Shut the Door… is ranked in the Top 5 of most any listing you can find.

2. The Wheel (Episode 1.13 Oct 18, 2007) — The Drapers – and the Campbells and the Cranes, for that matter – are facing family issues as Thanksgiving approaches. Kodak is not happy with how they are promoting their slide projector and Don gets to pondering it and considers his own family, past and present. Betty’s neighbour tells her tearfully that she discovered her husband is having an affair; she checked the phone bill and dialled an oft-called Manhattan number and a woman answered. Betty gets to thinking and checks her own phone bill. She tries a regularly-occurring number but it’s not a woman that answers it’s her own shrink. Betty is at first relieved then sad when she realizes the doctor has been discussing Betty’s therapy with Don. At her next session, Betty says things to the doc that she hopes he will tell Don. Don is ready to pitch his slide projector campaign to Kodak. He talks about having a “sentimental bond” with technology as opposed to simply the cold usage of a machine. Significantly, Don says to all assembled “Nostalgia; it’s delicate but potent”. His pitch brilliantly makes use of pictures of his own family, his own past. He puts himself into the pitch and this resonates with the Kodak boys. Don talks of nostalgia taking you “…to a place where we know we are loved. This has much import when looking at Don’s character; consider that, later on, in episode 6.8, referred to above, Don’s major life question is “does someone love me?“. Harry Crane, separated from his wife, is overcome and bolts from the room.

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In other business, Pete brings in his father-in-law’s account, Clearasil, prompting Don to promote Peggy to junior copywriter and put her on the account. Pete is apoplectic. This raises the question does Don set Peggy on her career path just to spite Pete? Peggy gets her first desk/office but feels sick and goes to the doctor. Peggy is dumfounded to find out she is pregnant; she gives birth to a baby boy but rejects him. Don, still feeling the family vibe from his pitch, goes home to an empty house and feels regret that he didn’t join his family for Thanksgiving; this is an early episode that depicts Don picking work over family. He slumps on the stairs as Bob Dylan advises him “Don’t Think Twice, It’s Alright”. The first season ends. This episode – that tops at least one list I saw – is perhaps significant because it features maybe the most poignant pitch of Don’s career, a pitch that showed audiences that this whole mid-century advertising thing has great depth and offers serious avenues of storytelling. In terms of Peggy’s character, having and giving up her baby does much to define her arc.

1. The Suitcase (Episode 4.7 Sept 5, 2010) — Sterling Cooper Draper Price is buzzing about the upcoming Cassius Clay-Sonny Liston fight; except poor Don who’s stressing over Samsonite. Peggy and her team have shown him their work and Don is verbally unimpressed. Unbeknownst to most – Don included – it is Peggy’s 26th birthday and she has a romantic dinner planned with her boyfriend. Don makes her stay late to work on Samsonite with him. Former SCDP employee, Duck Phillips, calls Peggy and drunkenly tries to hire her for an agency he wants to start; he also tells Peg he wants to resume their relationship but Peggy rebuffs him on both counts. Don is supposed to return a phone call from “Stefanie in California” marked “Urgent” but he puts it off. He and Peggy get to work on Samsonite although Peg is none too happy about being made to stay late and that her boyfriend is pressuring her to drop everything and come to dinner; he actually has a surprise birthday dinner planned and is sitting with Peggy’s family waiting for her. He and Peg fight on the phone and eventually break up. Resuming work with Don, she takes a drink and vents some long-submerged frustrations on him. While, again, Peggy is tough and goes toe-to-toe with Don, he cruelly shouts her down and she cries. 

The two eventually cool down enough to go to dinner, revealing things about themselves to each other. Peggy tells Don about her baby, a subject she never discusses. She tells him that the whole office thinks it was Don’s baby; in fact, her mother is convinced and hates Don because of it. Don seems struck by this and asks if she knows who the father is. “Of course, is all she will say. Back at the office, while a drunk Don throws up, poor Peggy encounters another drunk. Duck is stumbling around the office and spitefully tries to defecate on what he thinks is Don’s chair. Don runs into Duck and the two comically fight, Duck getting the upper hand. Don now is spent and he and Peg fall asleep on Don’s couch, Don’s head in Peggy’s lap. Early the next morning, Don summons the nerve to call Stefanie in California and is told that Anna has died. (To understand the true import of this, you have to know something about the history of Anna Draper and Dick Whitman/Don Draper) Don sees that Peggy has heard the call but he can’t help breaking down; Peggy consoles him. As it is morning now, he tells her to go home and get some sleep but she just lays down in her office. Later that morning, a fresh-looking Don summons Peggy into his office. They come to an agreement about Samsonite and Don suddenly squeezes Peggy’s hand and they share a significant look. Simon and Garfunkel’s “Bleecker Street” plays out what TV Guide calls “the 7th best episode of the 21st century”.

The Suitcase tops every list I looked at but two and on those it was second. The fact that this episode is considered the best Mad Men episode ever is extremely telling. As I watched it again recently, I at first struggled to see what was so significant about it. Then my film school-teenaged son – who also informed me this was a “bottle episode” – explained it by saying that Mad Men is about Don and Peggy. And while this halfway point of the series doesn’t have a new agency being started or pigeons being shot or an Englishman hanging from the rafters, what it does have is a showcase for perfect television depicting a pivotal moment in the substantial relationship between the two major characters. What you get from The Suitcase is Don and Peg airing out past grievances, Peggy revealing things about her personal and professional life to her mentor and Don letting Peggy see behind the curtain; simply allowing Peg to see him cry is huge but letting her know it is due to the loss of the only person who really knew him is also revealing to Peggy. Later in the morning when Don is back to business, making a point of stopping and taking her hand and really looking at her…that moment alone may be the most significant of the series in terms of the context of the show. I couldn’t help but think of some of the conjecture I’ve read concerning Don and Peggy’s role in creating the iconic Coca-Cola ad depicted in the series finale. The relationship between Don Draper and Peggy Olson may not only be the backbone of one of the finest TV shows ever made, it may also be the most compelling male/female relationship in television history.


Some indelible moments I can personally recall from the series include: Don takes his kids to show them the shabby childhood home he grew up in. Much is understood now by his daughter, Sally, who looks at him significantly (In Care Of Ep. 6.13). Don and Betty share a phone call during which Betty talks about her imminent death from cancer. It’s a heart-wrenching finale to their relationship (Person to Person Ep. 7.14). Married art director Sal Romano is given the chance to direct the new ad for Patio Cola. He acts out for his wife, Kitty, how the actress in the commercial will dance around. He acts like a woman so convincingly that his wife realizes he is gay, explaining why they have not been intimate lately. I often think about Kitty’s life after this revelation.

Watching these ten episodes – spread throughout the series’ run – has been wonderful. But it does present me with a problem; how can I not be watching this show all the time? I really should be constantly making my way through the show which has an embarrassment of riches; there’s no bad “eras” or “seasons”. No additions of a show-killer like Ted McGinley. Maybe we should just start again at the beginning or use this list as a playlist. Either way you can’t go wrong.

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