Mad Men's 12 Most Memorable Moments

Mad Men’s season finale Sunday found Don Draper making new commitments and facing the future. WATCH VIDEO of Jace Lacob’s picks for the best moments of Season 4.

10.18.10 5:26 AM ET

Mad Men’s fourth season began with what seemed like a simple enough question: “Who is Don Draper?”

It’s that query that has hovered uneasily over the action as viewers and Don Draper (Jon Hamm) himself attempted to solve that riddle. After the third season finale erased the foundation of Don’s life—removing him from wife Betty (January Jones), his suburban home, and his children—Don set out to find himself as a single man, embarking on a bachelor’s quest of depravity and excess.

Now one of the founding partners of Sterling Cooper Draper Pryce, the darkness that Don found himself in—one colored by drunken blackouts and whores, blind dates, and indiscretions with secretaries—seemed impenetrable at times, as Don sought out some new inner compass following the death of someone close to him, and perhaps of his optimism as well.

In the season finale, just as Don’s son Bobby (Jared Gilmore) wanted to fly a fighter jet rather than a flying elephant at Disneyland, so too does Don choose Tomorrowland over the past, proposing to his secretary, Megan (Jessica Paré), rather than go back to girlfriend Faye (Cara Buono). Megan’s optimism and buoyancy are at odds with the hard truths experienced by Faye.

“The real emotional underpinnings of the season were about Don: Who is Don, how is he going to survive, what is it like for a man of that age—forgetting that period—to have everything that defines him stripped away?” creator/executive producer Matthew Weiner told The Daily Beast over the weekend. “He uses himself a lot for the advertising. He isn’t even in the demo anymore…He had to figure out who he was.”

The 12 scenes selected from this past season of Mad Men reflect the diversity and scope of this gripping drama, moments that capture the characters at their most selfless and most selfish, relics of a bygone era who are still vibrant and recognizable to viewers today.

Episode 13, “Tomorrowland”: Don Proposes to Megan

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Throughout the season finale, the reality of the attraction between Don and Megan became increasingly obvious, from his offer to fly her to California to look after the children to her calmness at the diner when Sally (Kiernan Shipka) spilled a strawberry milkshake. Megan’s interactions with the children—from the first time Sally throws her arms around the secretary in “The Beautiful Girls” to that Maria von Trapp moment as Megan has the kids singing a French song as Don walks in the door—all point toward an idealized domesticity, something that bachelor Don hasn’t experienced in some time. But it was the suddenness of his proposal to Megan upon arriving back in New York that had even her gasping with surprise. All the more so given that he used the engagement ring that the real Don Draper had given the dead Anna (Melinda Page Hamilton), saying that it had been in his family for a long time. (The ring, let’s be honest, was the marital equivalent of Chekhov’s gun.) Has Don followed in the footsteps of mentor Roger Sterling (John Slattery) by taking a young bride? Or is Don hoping to buy into the dream that he himself created with his advertising, placing himself squarely back in the all-important demo again? Yet it’s worth noting that he’s still not sleeping soundly at night.

Episode 13, “Tomorrowland”: Don and Betty Once More at Ossining

It was fitting that the season should end with a final confrontation between Don and Betty in the kitchen of the house they once shared in Ossining. While the meeting appears on the surface to be a matter of chance, it’s interesting to note that Betty is first seen touching up her powder and waiting for something—waiting, of course, to bump into Don as he arrives, using a few forgotten odds and ends as the means to ambush him. Their shared drink speaks to a familiarity between them as well as perhaps a thaw in their frigid relationship, as Betty asks him to “remember this place.” But while Betty clings to their outmoded past—even as she attempts to exert control over the chaos of life by bulldozing her present (firing poor Carla, moving the kids)—Don wants to look forward and not back. As she fights back tears upon learning that Don has gotten engaged, Betty admits “things aren’t perfect.” But Don doesn’t fall for crocodile tears or cozy nostalgia, brushing her off with a line about her moving again if she doesn’t like her new house. Their relationship and the detritus of their marriage are all wrapped up with a simple exchange of the key to the house, the final coda to their tumultuous past, a tabula rasa for both parties. A house, it seems, does not make a home.

Episode 3, “The Good News”: Don Says Goodbye to Anna

While Mad Men has focused on Don’s romantic proclivities, arguably one of the most important relationships in his life was with Anna Draper (Melinda Page Hamilton), the wife of the real Don Draper, the man whose identity our “Don” stole during the Korean War. A strictly platonic relationship, the tie with Anna represented something pure in Don’s life, someone who knew all of his secrets and still loved him for who he was, not for who he claimed to be. Discovering that Anna has terminal cancer, Don is forbidden to discuss the matter with her, but Anna’s entreaties to Don to live his life and do what he wants are the words of someone who knows the end is near. After removing the water stain on Anna’s wall, he decides he has to leave. Their final moments together are an exploration of the impermanence of life. Don’s efforts to hold onto Anna—and his old identity as Dick Whitman—are like grasping at air. He can’t fight the forces of change, nor matters of mortality. Sometimes, it seems, all we leave behind is a mark on the wall.

Episode 7, “The Suitcase”: Don and Peggy Share a Moment

Don attempts to distract himself while he faces the inevitable death of Anna Draper. Paralyzed by his inability to do anything to save her, Don throws himself into work and ruins a birthday evening for Peggy (Elisabeth Moss) in the process. After a season of separate storylines, the mentor and student finally come together with a blistering argument about Peggy’s work winning Don the Clio Award, followed by dinner at a Greek diner and drinks. Back at the office, they fall asleep on Don’s couch, a portrait of non-sexual domesticity. After seeing a ghostly image of Anna, Don learns that she has died. Peggy’s effort to console a sobbing Don is a testament to the true emotion and rapport between them. Each has seen the other at their very best and worst, each has kept their share of secrets. Rather than sweep the moment under the rug (as he had done earlier in the season after his dalliance with his secretary Allison), Don admits that the moment did happen, taking Peggy’s hand in his and squeezing it gently the next morning. It’s a rare moment of honesty from a man so used to lying, a symbol of true friendship, respect, and acceptance.

Episode 12, “Blowing Smoke”: Why I'm Quitting Tobacco

After a season of Don writing in his journal, a rare bit of navel-gazing, the writers brilliantly paid off this storyline with the penultimate episode’s reveal, as Don—furious about the loss of both Lucky Strike and Philip Morris—writes a letter about why the agency is no longer interested in taking on tobacco clients. Contrasting the addictive quality of nicotine with the heroin addiction of Don’s ex-girlfriend Midge (Rosemary DeWitt), the high-minded letter runs as a full-page ad in The New York Times. Spelling out which ad agencies will still sell smoke, the letter is Don’s attempt to “change the conversation,” to reject the cigarette companies rather than vice versa. The partners are upset by Don’s solo decision, so much so that Cooper (Robert Morse) quits. It’s a decision that will either save Sterling Cooper Draper Pryce or doom it forever, a masterstroke that’s fittingly at odds with the season opener, in which Don chastised Peggy for “shenanigans.” Regardless, the conversation has most definitely been changed.

Episode 9, “The Beautiful Girls”: The Death of Miss Blankenship

Poor Ida Blankenship (Randee Heller). Bert Cooper’s former secretary was drafted to take over as Don’s Gal Friday after the affair with Allison (Alexa Alemanni) went horribly awry. Arguably a terrible assistant, Blankenship injected a hilarious streak to Mad Men’s fourth season, with her racist and overbearing nature, awful hearing, and messy demeanor. But for all of her comic relief, Blankenship became a tragic figure in the Mad Men mythos, dying silently at her desk. She died as she lived, “surrounded by the people she answered phones for.” Yet even in death, she’s used here to leverage the funny, as Pete (Vincent Kartheiser) and a teary Joan (Christina Hendricks) manage to drag her body out of view of the clients. But her death becomes a cautionary tale of a life lived in service to others rather than to oneself. Bert Cooper at least makes sure she has a suitable obituary, calling her an astronaut, a woman born in a barn who died in a skyscraper.

Episode 5, “The Chrysanthemum and the Sword”: Betty Unleashes her Fury on Sally

Grappling with life after her parents’ divorce—and her icy mother’s remarriage to Henry Francis (Christopher Stanley), Sally Draper (Kiernan Shipka) rebels in a number of ways, first by chopping off her blonde locks when Don leaves her with a babysitter. The fury of Betty is fully unleashed, as she slaps her daughter across the face, because Betty can’t physically lash out at Don, whom, she tells her new husband, she wants dead. Surprisingly, it’s Henry who is not only calm, but also a good and decent parent, understanding what Sally is going through. Later, however, relations deteriorate further when Sally is caught touching herself when watching The Man from U.N.C.L.E. Embarrassed, Betty threatens to chop off Sally’s fingers if she ever does it again. The extreme disconnect between mother and daughter finally leads to therapy, as Sally attempts to find a way of coping, even as Betty seems determined to make Sally pay for Don’s indiscretions and his “whores.”

Episode 9, “The Beautiful Girls”: Runaway Sally

Desperate to get away from Betty and Henry, Sally runs away from Ossining and heads to the city to be reunited with her father, hoping to move in with him. While Don is initially furious, the two share some tender moments as they order pizza, Sally makes him French toast (with rum), and they organize a trip to the zoo. But Don knows that he can’t care for Sally and, despite her efforts at manipulation, he brings in new girlfriend Faye (Cara Buono) to try and reason with Sally. Hysterical, Sally runs down the hall of Sterling Cooper Draper Pryce and falls. She’s consoled by receptionist Megan (Jessica Paré), rather than Faye or Peggy. Sally’s interaction with Megan points toward the protection and warmth that she’s missing in her life. With Betty arrived to collect her daughter, the women of the office gather in the doorway to see Sally off, forcing Betty to behave herself. Sally’s possible future is contrasted sharply with both the present day complications of these working women and the dead Ida Blankenship.

Episode 10, “Hands and Knees”: Joan Goes to the Abortion Clinic

Blue-coated Joan Harris, looking like a sad Madonna, sits in the waiting room of an abortion clinic as she prepares to have her third abortion, the result of her one-night stand with Roger Sterling (John Slattery). A series of mixed emotions play over her face as she considers the decision she’s about to make. With her in the room is a woman whose 17-year-old daughter is terminating her own pregnancy. As Joan attempts to console the woman, Joan can’t bring herself to tell her that she’s the patient, instead inventing a fictitious 15-year-old daughter of her own. The sadness that washes over her is keenly felt, even as she attempts to make this woman feel better about her plight. While it seems that Joan goes through with the procedure as she solemnly rides home, alone, on a darkened bus, we finally learn in the season finale that she didn’t go through with it after all. Instead, she smiles as she lies on the phone to Greg (Sam Page) about the paternity of the unborn child.

Episode 4, “The Rejected”: Allison’s Violent Outburst

If the season were largely about Don reflecting on who he is, it was also about the mistakes he made along the way. None was quite as large as falling into bed with doe-eyed assistant Allison, whom he drunkenly pulled on the couch after a night of carousing. Attempting to get back to normal, Don pretended that the incident didn’t happen and went so far as to offer Allison a cash bonus at Christmas. But later, after breaking down during the Pond’s focus group, Allison tearfully confronts Don in an effort to get him to admit that something took place between them. The tension of the scene is broken by Peggy popping her head up to see what’s going on in Don’s office, one of the funniest moments of the season.

Episode 9, “The Beautiful Girls”: Joan and Roger Reconnect

The star-crossed lovers finally get another chance, as Joan’s husband, Greg (Sam Page), is about to be sent off to Vietnam and Roger has realized his marriage to the pretty Jane (Peyton List) hasn’t blossomed into what he once had with Joan. After an awkward dinner at one of their old haunts, the two walk through a rough neighborhood and are mugged at gunpoint. Forced to give up her wedding band (just as her husband is sent off to his likely death), Joan is visibly shaken and distraught. Perhaps emboldened by their brush with death, the two begin kissing as Joan tells Roger not to stop, their reunion becoming a public tryst under a stairwell, the past and present colliding. But there’s no future for these two, at least not in Joan’s eyes. Despite her failed efforts to conceive a child with her husband, it’s Roger who finally but tragically manages to get Joan pregnant.

Episode 10, “Hands and Knees”: Lane Confronts His Father

Throughout the last two seasons, Lane Pryce (Jared Harris) has been the company’s straitlaced financial manager, holding on to the purse strings even as his marriage collapsed. Don’s noble experiment has left Lane bitterly alone, after his wife takes their children back to England without him. But love blooms for Lane in a very unlikely place, as he falls for black Playboy Club cocktail waitress Toni Charles (Naturi Naughton) and attempts to introduce his gruff father (William Morgan Sheppard) to her. Disgusted by Lane, Robert declines to joint them for dinner. He savagely pummels Lane over the head with the crook of his cane, then stands on his hand until Lane agrees to fix his marriage. The Victorian-era disconnect explains a great deal about Lane’s nature and his chilly demeanor. His heartbreaking “Yes, sir” to Robert shows us a man trapped by his upbringing.

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Jace Lacob is the writer/editor of Televisionary, a website devoted to television news, criticism, and interviews. Jace resides in Los Angeles. He is a contributor to several entertainment Web sites and can be found on Twitter and Facebook.