With a credits sequence that depicts a faceless man in an urban free fall, Mad Men takes a lineup of different characters and, on their behalf, asks the audience: “Are we to be judged for our best behavior or our worst?” Matthew Weiner’s legendary series seems to have settled his answer between the black and white, as his characters beg for forgiveness and seek renewal when at the bottom of the bottle and the basement of their luck.
In many cases throughout the show’s eight-year run, audiences were given ample opportunity to despise Don Draper. Despite his many shortcomings, however, they always forgave him. Rude awakenings and realities are juxtaposed by the unavoidable desire for decorum in mid-century America. In watching the show from beginning to end, Mad Men suggests that even during our hardest free falls, the pavement will always there to wake us up.
These are the 10 Best Episodes of Mad Men.
10 “Smoke Gets In Your Eyes” (Season 1, Episode 1)
Who is Don Draper? When we first meet the Dick Tracy-cut character, he sits alone in a boisterous bar with a napkin, a cigarette and a half-downed Manhattan. He looks distant, almost lost. He’s on a deadline for a cigarette campaign that will make or break his ad-man reputation. He looks around the bar and sees everyone chuffing on a cancer stick, and though he’s been given the golden “I love smoking” line by an honest bar attendant, he finds himself at a loss.
Another Manhattan won’t do it, and cigarettes only drive him further into the dissatisfaction of his mind. This quickly leads to Don’s go-to antidote for mental blocks: women. Midge is his artist squeeze and his muse. He half-heartedly but believably insists that they should get married.
As he and Midge enjoy their post-conquest cigarettes, he invariably returns to the subject of his advertorial needs. He is insecure. He is needy. The sex, the drink and the cigarettes have done nothing. Don Draper needs answers. So begins the show.
9 “The Wheel” (Season 1, Episode 13)
“No one knows why people do what they do.” Whether it’s moral relativism or a genuine plea to the gods for direction, Don Draper has steadily pulled back the curtains from his life and let us see what lurks in the shadows. He’s not the only one. Affairs abound in season one of Mad Men and the victims of the love crime start to catch on.
Betty Draper gets a visit from her friend Francine, who has recently identified her husband as a cheater. When she reflects this story to Don, she looks at him with the eyes of a knowing wife, every word she utters reflecting her pain. Don can barely stomach the subtext, but in his now infamous Kodak pitch, he uses the Carousel to let the clients peek into his own life that he so recklessly lives out. Harry, with all of his matrimonial mishaps, can’t take the message and leaves the room bawling. When Duck says, “Good luck at your next meeting,” he seals the deal for Don.
8 “Meditations In An Emergency” (Season 2, Episode 13)
In the season finale of Mad Men’s sophomore year, Matthew Weiner frames the interpersonal crises against the backdrop of the Cuban Missile Crisis. Intercut with bits from John F. Kennedy’s speech to the nation on the mid-Atlantic conflict, “Meditations In An Emergency” moves the chess pieces to increasingly precarious positions.
Like one of his signature drinks, Don and Betty are truly on the rocks. In 25 episodes, Betty has evolved from loyal and patient housewife to a cynical, boozing and philandering woman. At the end of season 2, she is faced with an unwanted pregnancy and the choice of embracing the very lifestyle she despises, or returning to her more conservative roots. She dabbles in the dark side before racing back towards the safety of home life.
7 “Guy Walks into An Advertising Agency” (Season 3, Episode 6)
If this were an episode of Friends, it would be titled, “The One With The Lawn Mower.” Whether you think of it as schlock or brilliance, the John Deere incident takes the notoriously slow-strolling Mad Men tempo and kicks it into overdrive. As the sauced up secretary rides the lawn mower sans license, she completely upstages Joan’s departing conversation with Peggy by riding it straight over the foot of her incoming boss and launching blood all over the office and into everyone's drinks.
It’s the kind of Tarantino-esque moment that could (literally) make the show lose its footing, but thankfully only one person has that fate. Roger’s reaction encapsulates his wry effect on the show. With blood-splattered on the glass wall outside the office and his shell shocked office compadres along side him, he quips, “Jesus! It’s like Iwo Jima out there!”
6 “Public Relations” (Season 4, Episode 1)
With Sterling, Cooper, Draper, Pryce in full swing, Season 4 shows Don Draper at the height of his advertorial powers and the plinth of his relationship woes. The 40th Mad Men episode fittingly opens with an interview between Draper and a journalist from Ad Age, and while the “who is Don Draper” question is asked in earnest, few legitimate answers are given to satisfy it.
When he agrees to go on a blind date set-up by silver fox Sterling, he begrudgingly accepts the invitation, thinking the girl in question would be an easy conquest. To the contrary, Bethany challenges Draper’s expectations and merely gives him a kiss at the end of the night. His best moves are rejected. In other news, Peggy continues to improve her stock at SCDP, offering the funniest interaction of the episode with Joey with their, “John!” “Marsha!” inter play.
5 “The Suitcase” (Season 4, Episode 7)
Platonic relationships between men and women are rare in television. They challenge the trope that love and romance are the definitive forms of cross-gender interaction. Don Draper and Peggy Olson have love for each other, and while they verge on actualizing their mutual care and respect, it remains distinctly professional and almost sibling-like in their interaction.
“The Suitcase” arrives smack dab in the middle of the fourth season and plays out like a movie in its dedication to the two leads, Don and Peggy. Through their verbal play and interaction, we recognize that their relationship is preserved and improved by their lack of consummation. For Don, sex wrecks everything. For Peggy, it hasn’t been much better. Together, they elevate each other and forge a business and personal bond that can weather the worst of storms. So when Peggy cries to him that he “never [says] thank you,” and he retorts, “That’s what the money’s for!” you know that the words are a fleeting fight that will ultimately be resolved.
4 “The Other Woman” (Season 5, Episode 11)
In Mad Men, some characters survive traumatic experiences and learn from them, while others fall further into their recidivism and repeat the mistakes of the past. In “The Other Woman,” Pete Campbell fulfills the full potential of his sniveling creepiness by fronting Joan as a Madison Avenue courtesan. Despite Don’s protestations, Joan accepts the degrading act in exchange for a piece of the company and promotion to partnership.
Her willingness to comply with the archaic demands of Herb, the Jaguar client, shines a light on each of the SCDP men who counsel her in various ways. Some responses are selfish (Lane Pryce in all his English importuning), others are chauvinistic (Pete Campbell), and others are bewildered (Don, who clearly draws on his origin story as the son of a prostitute). Joan is above it all. She knows what she stands to gain, and since “The Smoke Gets in Your Eyes,” she has had the drop on every man in New York. When she acquiesces and allows the subsequent defilement, she embraces a future free from want.
3 “Far Away Places” (Season 5, Episode 6)
If the midway point of Season 5 is about the desire to escape, then it is equally adamant about our inability to truly do so. Impromptu vacations and psychedelic drugs may provide momentary distractions, but in doing so, they can also offer incisive reflection onto the shortcomings of daily life. Don and Megan gallivant in Pittsburgh, with all the makings of a romantic getaway, only to find that the romance has indeed long gotten away.
As Megan returns to her New York flat by bus and taxi, Don searches for her in a panic. He arrives back at their apartment to find the door locked and Megan hiding inside. While Don kicks the door down and chases his wife around the apartment, tackling her in the living room, he chases the love they once had as it slips from his fingers. “Every time we fight, it just diminishes this a little bit,” Megan cries. For Roger and Jane, LSD seems like the perfect gateway to internal exploration and external joy, but it ultimately ends in their agreeing to divorce. In “Far Away Places,” temporary escape has lasting consequences.
2 “Commissions and Fees” (Season 5, Episode 12)
In Matt Weiner’s advertorial opera, “Commissions and Fees” becomes his “Death of a Salesman.” He casts Lane Pryce as a Brit in the stereotypical American role, and going one further than Arthur Miller, uses Don Draper as the counterpoint.
Whereas the latter man knows the art of identity shifting and forming, fully rooted in his own egotistical self-belief, Lane cannot break his fatalist outlook and find a future of hope. Lane lacks the American drive to ignore the naysayers and fulfill his destiny, but he has the Willy Loman penchant for insecurity and depression that ultimately carries the highest expense. Don himself coaches the caboose of SCDP, but his wise words do little to discourage the man from suicide.
When the partners find Layne draped behind the doorframe, they fulfill their fraternal obligations and cut him down from his corporate gallows. Their expressions read like a human epitaph: here lies the kind victim of a cruel world.
1 “New Business” (Season 7, Episode 9)
The closing shot of “New Business” shows an Emperor with no clothes. When Don returns to his digs and finds them completely free of any furniture, he gives a perplexing look of simultaneous panic and relief. For a man so content with his own ability to recreate, material goods have always been niceties but never been necessities. When he lived by himself in the fallout from his marriage to Betty, he thrived in a Spartan environment with retro items and dim lighting. As long as he had his brain and his booze, he would be OK.
As one of the closing episodes of Mad Men, “New Business” emphasizes Don’s recurring obsession with brunettes. He cannot shake their gaze, so when he meets Diana at the diner, he knows he must have her, at his place or in the restaurant alley. This time, however, it’s not just about conquest. He sees a sadness in her eyes that speaks a language he can understand. While he is only given access to her physical self, we are given a lasting glimpse into Don Draper that reminds us of his perpetual longing for fulfillment and understanding.
Those are our ten favorite Mad Men episodes. What are yours? Be sure to tell us in the comments below!