Mad Men’s fifth season, which came to a close on Sunday, began with the joy and optimism felt by newlyweds Don Draper (Jon Hamm) and Megan (Jessica Paré), only to slowly let in a narrative darkness that manifested itself in squandered dreams, hopeless enterprises, larceny, and even the death of a major character. Husbands and wives warred, ex-spouses sniped, children grew into adults, and partners fell out.

This all played out against a backdrop of monumental social and political change during which Sterling Cooper Draper Pryce hired its first African-American employee and gained its first female partner, though in both cases, there was an element of subterfuge rather than of progress. A joke ad stating that SCDP is an “equal opportunity employer” forced the partners to hire a black woman to be Don’s new secretary; Joan Harris (Christina Hendricks) was made a partner, but only because she sold her body to land them the lucrative Jaguar account. There is a sense that these “advancements” only perpetuate the norms rather than shatter them.

But regardless of the reasons behind these developments, each represents change in its own way, and that is one of the many themes playing underneath the fifth season, including the ending of the mentor/protégé dynamic between Don and Peggy Olson (Elisabeth Moss), who quit the firm to make her own way in the world. With an end date in mind for Mad Men (only two more seasons!), creator Matthew Weiner has shifted the drama into its final act before viewers’ eyes.

The 13 scenes below capture some of the most surprising, exciting, thrilling, or heartbreaking moments of the fifth season of Mad Men. WARNING: Proceed with caution if you are not completely up-to-date with Mad Men, as specific plots and narrative twists are discussed at length.

Episode 513, "The Phantom": Into the darkness

The final minutes of the season tightly strung together three sequences, each with its own narrative weight. In the first, the partners traveled to the 38th floor of the Time-Life Building to see their expanded office space, as Joan scored the floor with an "X" to mark the spot for the staircase. As they stare out into the space beyond the building, their silouhettes recall the opening credits of Mad Men and its promotional material, all black and white and red (the red of Joan's dress to be precise), framed by the yellow columns of the empty space. While it represented possibility, a blank slate, it also represented an emptiness that needed to be filled. Throughout the season, the characters have attempted to fill their own voids with sex, affairs, money, careers, and ambition. But there is always more space to be filled, an unending vastness to the chasm in themselves.

Those stark images gave way to the brightness of a fantasy. Or specifically, to the set of a shoe commercial where the fairy-tale story of Beauty and the Beast was being enacted. Overflowing with color and light, it was almost difficult to look at the shininess of the surfaces, the jewel-like glamour at play within the falseness of the situation. While it was Don who got Megan the job, as he chose not to follow the bitter advice offered by Megan's mother, Marie (Julia Ormond), there was a sense of folly here, even as Don made good on his efforts to improve the life of his spouse.

While Megan was overtly cast in the role of "Beauty" here, with all of its possible connotations intact, Don stepped away from the glowing light of the scene, the false lure of the fairy tale that Megan offered him. Instead, he moved beyond the artificiality of the environment of the studio, past the lights and the cameras, and into the darkness, which only too willingly swallowed him up. His path here returned Don to the void offered by his glimpse down the elevator shaft earlier this season, a darkness he avoided by not making the wrong step. But Don's typical salves—alcohol, women, work-—do little to dull the pain that exists within him.

Even his attempt to escape to the movies became instead a painful reminder of what he has lost when he ran into Peggy, herself looking to "brush off the cobwebs." An escape is sometimes just exchanging one problem for another, something summed up by the final scene of the season. At a bar dark, Don was asked by a beautiful woman whether he is alone, the final question of the season left unanswered, hanging in the air like a wisp of smoke. He's the titular phantom here, a wandering ghost. For Don, it seems, even in the presence of such beauty, is always surrounded by darkness, always alone.

Episode 513, "The Phantom": Extraction

It hardly came as a surprise that Don would be affected by the death of Lane Pryce (Jared Harris), particularly given that it was Don who forced his hand by demanding his resignation...and that he would be the one to cut him down from his noose. It's not the first time that Don has perhaps blamed himself for the suicide of someone in his life: his brother Adam (Jay Paulson) hanged himself as well, after Don refused to acknowledge him back in Season 1. With Lane on his mind—that empty chair at the partners' meeting holding only Lane's unseen ghost—Don was plagued by several phantoms, most notably that of the long-dead Adam, who appeared throughout the episode, turning up at his office and beside him in the dentist's chair.

While Don was at the dentist's office to have an abscessed tooth extracted, Adam's ghost served as a reminder both to Don and the viewer that there are some things that can't be fixed, and that some rot goes too deep to be extracted. That tooth, sitting bloodied beside him, was a piece of Don that was dark and rotten, but its departure from him didn't solve the deeper pain beneath the surface, a notion that played out within the episode. Pete Campbell (Vincent Kartheiser) realized that he cheated in an effort to reclaim the youth and vitality lost to him. Beth Dawes (Alexis Bledel) underwent electroshock therapy to cast off the gray clouds surrounding her. But those changed nothing in the larger scheme of things. A tooth can be removed, a bandage, as Pete said, can be placed over an old wound, memories removed, but the old hurts, the old pains have a nasty way of resurfacing. The rot just keeps on festering.

Episode 511, “The Other Woman”: Peggy resigns

Over the course of five seasons, Mad Men has navigated the often-tumultuous psyches of the ad men and women of Sterling Cooper Draper Pryce and explored various dynamics and relationships, the most important and central of which is that between Don and Peggy. The show, after all, began on her first day of work at the agency, as she was assigned to be Don’s secretary, and what followed charted the highs and lows of their working relationship, one built on loyalty and more than a few secrets. When Don finally opened up to Peggy—in the landmark episode, “The Suitcase”—a door opened between them, allowing Peggy to tell a tearful Don that she knew the “real” him, and for Don to acknowledge that a moment had passed between them. He did so without words, but with a silent gesture, a squeeze of her hand, a symbol of understanding and of unity.

In “The Other Woman,” a trough in their relationship was instead witnessed, as Don literally threw money in Peggy’s face in a gesture of frustration. For Peggy, it was a clear sign that she had to leave the agency and forge her own path; she accepted a job as copy chief at SCDP rival Cutler Gleason and Chaough. But it was the confrontation between Peggy and Don, in which she gave Don her letter of resignation, that gave the episode—about men’s desire to own and possess beautiful things—its narrative heft. As Don alternately raged against Peggy, pleaded with her, and tried to buy her back—demanding that she name a price—Peggy stood firm, refusing to be owned.

It was a transformative moment for Peggy Olson, positioning her as less Don’s protégé and more his equal (“You know this is what you would do.”) and when Don seized her hand and kissed it, it spelled out precisely why Peggy needed to leave: He will never see them as partners, but rather views her as an extension of himself. Her effort to shake his hand, to position herself as a masculine counterpoint to Don, resulted in that kiss, a sign of devotion to be sure, but also of male dominance. By withdrawing (it’s she who pulls her hand away when he will not or cannot), Peggy regained her independence. Her goodbye to him—“Don’t be a stranger”—contained more bottled emotion and meaning than many shows contain in their entire run; these two who know each other inside and out could never be strangers in any sense. Their parting is both full of pain and of possibility and, as Peggy stepped into the elevator, it was impossible not to see the opportunity ahead for her.

Episode 508, “Lady Lazarus”: Don faces the void

Death imagery swirled around the fifth season of Mad Men rather overtly as characters so frequently indulged in casual mentions of suicide, rifles, insurance, and other life-and-death ephemera that it was impossible not to see death as an inevitable conclusion. By weaving it into the narrative, Weiner and his writing staff created an atmosphere of dread and impending doom that felt both logical and inexorable in retrospect. A daily activity—waiting for the elevator to arrive at work—became something perilous and startling, an unexpected brush with death in the most mundane of environments, as Don decided to chase after Megan, who had quit the firm, as she left the office for the last time. When those elevator doors opened, as they’ve done countless times in the Time-Life Building, Don nearly stepped into an open elevator shaft and met his maker. The implication here—that Megan is achieving lift-off just as Don is going down—is as keenly felt as is the sense that there is no exit for Don, elegant or otherwise. In chasing after her—and perhaps by stopping her from leaving—Don risked losing himself.

Episode 512, “Commissions and Fees”: Lane commits suicide

Few viewers expected that mild-mannered finance executive Lane Pryce would take his own life, though, in hindsight, all of the warning signs were there that he would do something foolish before the season ended. After all, this was a man who illicitly took out an additional line of credit for the firm and tried to pass off the cash as an overage in order to pay out Christmas bonuses—and thus pay off the back taxes he owed to the British Inland Revenue. When that failed, he forged Don’s signature on a check and embezzled money from the company. He made a pass at Joan, only to be gently rebuffed, and engaged in a fantasy of an unseen mistress whose photo he stole from the wallet of her married lover.

In other words: Things were never going to end well for Lane, and when he was caught by Don and forced to resign, Don gave him the weekend to concoct “an elegant exit.” Lane did just that. After failing to die by his intended method, carbon monoxide poisoning in his new Jaguar (a present from his wife, purchased with funds they didn’t have), when the car fails to start—a masterful payoff to the notion that 1960s Jaguars were lemons—Lane instead hanged himself in his office. He was discovered the following day by Joan and his co-workers, his only suicide note a boilerplate resignation letter. This was telling on so many levels: his resignation wasn’t just from work but from life, and the lack of emotion or personalization implied that his entire identity was caught up in his professional career. Without one, he lost the other. It was Don who ordered Lane cut down from his noose and who arranged his body on his couch, attempting to give his disgraced former colleague a modicum of the dignity he carried himself with in life.

Episode 511, “The Other Woman”: Joan receives an indecent proposal

One of the most deeply polarizing and controversial moments of Season 5 was that of the indecent proposal offered to Joan: if the firm wanted the Jaguar Dealership Association’s support for their pitch, the head of the organization, Herb Rennet (Gary Basaraba), wanted an evening with the curvaceous redhead he had spotted in the office. While Don was against the entire idea—he wanted the creative to stand on its own and get them the account, not because of some dirty arrangement—the other partners vote to offer Joan $50,000 … in exchange for her essentially prostituting herself. Facing a divorce from her husband, Greg (Sam Page), the money offered tangible financial security to Joan, who was offered the proposition by Pete Campbell.

It was actually Lane who convinced her to go through with the sordid encounter, but he encouraged her to demand a partnership stake in the firm equal to five percent, which he said could “support a woman and her child for a lifetime.” While Joan believed that it was because of his feelings toward her, Lane’s true motivations were anything but altruistic: In persuading Joan to take future earnings over a cash payment, Lane was attempting to divert attention from his own embezzlement and from the line of credit he took without consulting the partners. Instead, Lane positioned his pleas as being the best for both Joan’s well being and the company’s, but it was a selfish move and demonstrated just how trapped Lane was by his own actions.

Joan ultimately went through with the plan, selling her body for a piece of SCDP. Don showed up at her apartment to try and dissuade her from going through with the prostitution scheme (“It’s not worth it”) and the scene that passes between them—as Joan touched Don’s face and told him that he was one of the “good ones” when she learned he had been against all of it—is all the more heartbreaking because the viewer later learns that it was too late: the encounter had already occurred, and the emerald necklace that Joan received from Herb, a trinket of affection, became a literal chain around her neck, a symbol that, like that the Jaguar itself, she is “something beautiful you can truly own.”

Episode 501/502, “A Little Kiss”: Megan serenades Don

Already an iconic sequence in the mythos of Mad Men, the fifth season opener contained Megan’s unexpected performance for Don at his surprise party, a sexually charged rendition of “Zou Bisou Bisou” (memorably performed by Sophia Loren in 1960 film The Millionairess), that left all of the party guests with their mouths agape in jealousy. Her serenade, in which she willingly transforms herself into a French coquette, demonstrates something not seen on Mad Men before, most notably a woman exerting ownership over the masculine gaze in the room and her own sexual hunger, which plays out in an exhibitionist streak in front of Don and his guests. (She earlier told Peggy that when she throws a party, her guests go home after and “have sex.”)

Despite the overt sexuality of the performance, Don was displeased by the intrusion of their personal life into his professional world, the collision of two spheres that he had always tried to keep separate. Her gift became instead a wedge between them and Don went to bed churlish and angry, leaving Megan confused about her husband’s reaction. The Monday after, however, the two engage in a sex game as Megan, cleaning up after the party in a black bra and panties, flaunted her body to her husband and told him that he didn’t deserve to touch her, but could instead sit and watch her, another inversion of the male gaze in which she was willingly objectified by his attentions, but retained the upper hand within their game of dominance/submission. It coalesced into an encounter on the white shag carpeting, the kinetic fulfillment of the sexual energy of her “Zou Bisou Bisou” performance.

Episode 505, “Signal 30”: Pete and Lane brawl

“Signal 30” was presented as a look at the emasculation of Pete Campbell, referred to within the episode by Lane as a “grimy pimp,” a bit of foreshadowing that later played out in “The Other Woman.” But within this installment, a glimpse into the conflict within Pete was offered, as his journey to claim his manhood was challenged by several obstacles in his way. His efforts to seduce a girl (Amanda Bauer) in his driver’s education class were thwarted by the appearance of a younger, better looking guy who is literally nicknamed Handsome (Parker Young). His efforts to fix the kitchen sink—spraying water all over wife Trudy (Alison Brie) during their suburban dinner party—went painfully awry. While he messed around with his red toolbox—a symbol of his own fussy masculinity—Don stripped off his shirt and fixed the sink, much to the delight of Trudy and the women, stealing both the glory and the female attention. His bedding of a prostitute was preceded by her attempts to find the right way to turn him on: by making him a king, the hero of his story, a role he sees as co-opted by his new life in the suburbs as a husband and father.

The evening of debauchery led to the (temporary) loss of the Jaguar account (thanks to the wife of David Hunt’s Edwin Baker finding “chewing gum on his pubis”), something that Lane had finessed in his own inimitable way due to his friendship with Edwin. When Pete then further impugned Lane’s manhood, telling him that Edwin thought he was a “homo,” Lane challenges him to a fistfight in the conference room of SCDP. The fight offered an opportunity, whether real or imagined, for both to salvage their wounded male pride and reclaim their self-identities as men. While it was Lane who knocked Pete to the ground as the others watched from the sidelines, Lane himself doesn’t regain his psychological balance: the fistfight instead made him question, “What do I do here?” It’s a question that is as much about work as it is about life.

Episode 510, “Christmas Waltz”: Don and Joan play house

There is likely a ton of fanfic already written about the particular pairing of Don and Joan, but while Mad Men has teased the flirtation between the two, it has never crossed into consummating the simmering sexual tension. The easy intimacy between Don and Joan was captured in “Christmas Waltz” over the course of an afternoon after Joan received divorce papers from her husband. After posing as a married couple and test-driving a Jaguar, the two head to a bar where they drink away the afternoon and engage in the sort of telling banter that comes from working side-by-side for years. His chivalry—subtly demonstrated in “The Other Women—was also seen here as Don offered Joan both his coat and an escape route from the office; their play-acting allowed them to transcend the boundaries of their respective roles: husband, father, ex-wife, single mother.

Their perfect banter (“My mother raised me to be admired,” Joan coos at one point when asked about the flowers she received from suitors) electrified here, but the two kept their dynamic entirely platonic in the end, with Don sending a bouquet the next day. The flowers were not for Megan, who threw a tantrum when he returned home late that night, reeking of booze, but for Joan, and he jokingly signed the card “Ali Kahn.” While Don was play-acting at romance with Joan, his home life was becoming increasingly fraught. But both Joan and Don got to pretend to be someone else entirely. For one afternoon, Don and Joan were just a man and a woman, drinking together in a crowded bar.

Episode 508, “Lady Lazarus”: Pete and Beth’s sad tryst

Largely thwarted in his attempts to regain his youth, Pete Campbell embarked on a one-night stand with unhappy housewife Beth, the wife of his commuting buddy Howard Dawes (Jeff Clarke), an adulterer who purchased an apartment in Manhattan for his illicit affair. When Pete encountered Beth stranded at the train station, he drove her home, only to end up having sex with her on the floor of her suburban home in Cos Cob, Conn. Despite the “reckless” element of their tryst, the after-effect of their romp was anything but romantic, rendered in a light that was deeply tragic. An already clingy Pete refused to see that this was a one-time deal, as he tried to seduce Beth into becoming a regular fixture in his life. The conversation that followed their consummation had Beth describing Pete’s eyes as being as shockingly blue as the Earth in space, which he viewed as a compliment. Rather, she viewed those photos of the planet as being “surrounded by darkness,” vulnerable and alone. While the allusion referred to Beth as well, it summed up Pete’s entire sense of gravity this season, as well as his isolation.

Despite having a wife and baby daughter at home, Pete quickly became consumed by thoughts of Beth, later fantasizing in a straightforward Freudian daydream about her appearing at the office wearing nothing but a fur coat. His refusal to leave their affair in the past resulted in him forcing his way into Beth and Howard’s house on false pretenses, where he tried to get her to meet him at a hotel. She failed to turn up—his frustration captured in a futile gesture of rage (as he throws a glass against a wall)—but a chance encounter at the station had her drawing a heart in the steam of her car window. Beth’s heart is a reminder of how quickly these scenarios can dissipate, despite how much of a lure it represents to Pete, who clearly wants to explode the suburban idyll he had found himself stranded within. In losing his dream of happiness, Pete had lost himself. Both he and Beth were unmoored, alone, traveling in an orbit that could not be broken, feeling the heat but never catching up to it.

Episode 503, “Tea Leaves”: Betty’s weighty issues

It was unclear just how actress January Jones’s advanced pregnancy would tie into Betty Francis’s story arc this season, but Matthew Weiner and the writing staff managed to surprise viewers by unveiling the new, but not necessarily improved, Bugles-chomping Betty, who had gone up quite a few dress sizes since we last saw her at the end of Season 4. But the plot went beyond mere shock, instead choosing to use Betty’s ballooning weight as a crucible through which to test her character. The possibility that her weight gain could be the result of cancer allowed Betty to be seen in a different light; her phone call to Don—in which he called her “Birdie,” a lovely callback to the early seasons of the show—captured an unexpected tenderness that had been lost during years of venom between them. Likewise, there was a beautiful, elegiac quality to the scene in which she hugged baby Gene tightly to her as the Fourth of July sparklers lit up around them, expressing the fear that she would never see this boy become a man etched clearly on her face as real as the dream she experienced in which her family mourned her death.

What followed in the wake of her discovery that she didn’t have cancer also further defined Betty’s polarizing character: the Weight Watchers meetings, the way she weighed the cubes of cheese and burnt toast, that single Brussels sprout she takes for Thanksgiving dinner. But it was the scene in which she ate an ice cream sundae and then greedily finished her daughter’s dessert when Sally (Kiernan Shipka) said she was “full” that spoke volumes about Betty’s fear: that she has been supplanted, replaced as the beautiful blonde creature who turned everyone’s head. One can see Betty’s decision to finish the sundae as an acknowledgement that she’s lost the battle, allowing her daughter to take over her role as the girlish waif with the feminine figure. Instead, Betty eats to fill a void in her life and in her self.

Episode 506, “Far Away Places”: Roger takes a trip

One of the most surreal subplots this season was the acid trip embarked on by Roger (John Slattery) and his estranged wife Jane (Peyton List) at a party hosted by Jane’s psychiatrist, Catherine (Bess Armstrong). And what a trip it was, connecting thematically to the detours taken by Don and Peggy in the same episode. Roger’s lucid vision quest took the viewer into the recesses of his subconscious, where he witnessed the 1919 World Series, imagined his partner Bert Cooper (Robert Morse) appearing on a five-dollar bill and bottles of alcohol transforming into orchestras, and saw Don appear out of thin air, taking over as his vision guide. What was intended to be a shared experience for Roger and Jane became instead their final voyage together as they discussed splitting up, something both had considered, but been too afraid to say aloud, until the liminal state of the acid trip freed them up from their inhibitions. After they came out of their shared dream, those inhibitions were once again raised, as Jane denied discussing ending their relationship. A yellow rose, given by Roger to Jane, became a symbol of the transitory stage of their marriage. Vivid and in bloom, by the following day, the flower’s petals were strewn over their marital bed, already dying.

Episode 507, “At the Codfish Ball”: Sally grows up, sort of

Sally Draper, frequently presented as teetering unsteadily on the precipice between childhood and adolescence, tried to push herself into adulthood in “At the Codfish Ball.” After Sally accidentally caused her step-grandmother (Pamela Dunlap) to break her ankle, she and her brothers went to stay with Don and Megan, where Sally attempted to position herself into the role of modern woman, both embodied by the ensemble that she purchased with Megan—complete with go-go boots, copious makeup, and a sleek, modern dress—and her behavior patterns as she sampled fish, a food she previously hated, and played at being Roger’s “date.” (She offered him, per his request, a “get ‘em tiger” as her role required, as she sipped a Shirley Temple.) But it was what Sally saw—Megan’s visiting mother, Marie (Julia Ormond), going down on Roger in a back room—that reminded her and the audience that she still had her innocence and that, for all of her romantic notions (she expected to enter the ball via a stunning staircase in an entrance worthy of Cinderella), she wasn’t ready to take the plunge into adulthood. When recounting her trip to her friend Glen (Marten Holder Weiner), Sally summed up her visit to Manhattan in one word: “Dirty.”