One of the many reasons Mad Men has kept us hooked for five-plus seasons is its ability to cram (approximately) an entire year’s worth of action into 13 episodes, and yet the last moments of every season finale make it seem as if the drama is just beginning. In Season Three, we ended on the first day of Sterling Cooper Draper Pryce's existence. Season Four it was Don and Megan's surprise engagement. But it was the bleak Season Five (one episode was called "Dark Shadows," for heaven’s sake!) that gave us Mad Men's most cliffhanger-esque finale to date: For a good nine months, we’ve been dying to know what Don’s answer to that mysterious blonde in the bar was – or what year the show will even be in when it returns this Sunday. So as we wait with bated breath for what the sixth season premiere will yield, here's a cheat sheet of the SCDP crew's most pernicious antics from May 1966 to spring 1967.
WARNING: MAJOR SPOILERS FROM SEASON FIVE AHEAD
Throughout Season Five, many viewers had one repeated question for Jon Hamm’s alter ego: "Who are you and what have you done with Don Draper?" Aside from a spooky fever dream in which he slept with and killed a former conquest, Don, for the first time in Mad Men's history, maintained a sole sexual partner for a whole season – his sultry new wife, Megan. But any fair-weather viewer could see how much of a struggle fidelity was for Don, no matter how many times Megan flashed her boobs in the office or serenaded him with "Zou Bisou Bisou." By the season’s end, Don, racked with guilt over Lane Pryce's suicide (which manifests in visions of his also-dead-by-a-self-inflicted-hanging half-brother, Adam Whitman), found himself potentially exiting his marriage stage left – illustrated in the now-iconic shot of the camera pulling away from Megan about to shoot her first commercial as Don walks off the set – and toward a crossroads. Our final view of Don is of him contemplating the loaded question posed by a female stranger in a bar: "Are you alone?"
She broke through the countless glass ceilings at both Sterling Cooper and SCDP, but Peggy's lack of a penis continued to thwart her climb up the corporate ladder. Between her protégé, the outspoken, loud-jacketed Michael Ginsberg, usurping her success and Don disrespecting her opinions by tossing a wad of cash in her face, Peggy decided she'd had enough and got herself a shiny new copy chief position at rival firm Cutler, Gleason and Chaough. When we last see her, she is luxuriating in her Richmond, Virginia, hotel room, having experienced her first-ever plane ride and business trip, ostensibly for the account that would become Virginia Slims cigarettes. Peggy's relationship with brash journalist Abe Drexler reached a new level in the fifth season as well. During a romantic dinner at Minetta Tavern, he proposed – that they move in together. Although traditional-minded Peggy was disappointed that there was no ring in the offing, she accepted, causing a rift between her and her staunchly Catholic mother in the process.
While the word "faithful" could never be used to describe the SCDP junior partner's attitude toward his marriage, Season Five saw Pete pick up the tortured-womanizer torch Don left behind once he tied the knot with Megan. Pete brought in more business than ever before, but he paid the price with his personal life. Bored with Trudy, her revolving wardrobe of frumpy housecoats and their quiet life in suburban Cos Cob, Connecticut, city boy Pete struck up a flirtation with a high school coed, sought the company of hookers and eventually entered into an affair with his commuting buddy's wife, Beth Dawes. But no amount of surreptitious hearts drawn in a foggy car window could save this ill-fated romance: When Beth voluntarily underwent electro-shock therapy, her entire memory of Pete was erased. A despondent Pete subsequently got into a fistfight with Howard Dawes on the train, prompting Trudy, who thinks Pete's bruised face is the result of yet another car accident due to fatigue, to suggest her husband take a pied à terre in Manhattan. What Trudy doesn’t realize is she's just delivered Pete straight into the arms of more adultery.
SCDP's director of agency operations embodied feminist empowerment at the start of this season – and then became the subject of endless debate as she traded on her sex appeal for money, power and security. We all applauded new mother Joan for kicking her hotheaded bully of a husband, Greg, to the curb in the fourth episode – even though I still feel that by not mentioning that baby Kevin was, in fact, Roger's son was a missed opportunity in Greg's deserved emasculation. But reality for Joan quickly set in, as she realized she is now a single mother who needs to provide for her child. Enter Pete with the answer to her prayers, disguised as an indecent proposal: Spend one night in heaven with a Jaguar exec, and the account will be SCDP's. After a drunken heart-to-heart with Don (who cautioned her against whoring herself out for the sake of the company) and an honest financial discussion with Lane, Joan named her price – a partnership – and ultimately did the deed. In the season finale, as Joan shows her fellow partners around SCDP’s potential new second floor, she marks her territory as an executive with a can of red spray paint and by wearing a bright crimson dress.
Betty's petty jealousies got progressively worse during season five, in spite of the character's limited appearances due to January Jones' real-life pregnancy. The character scored a brief moment of audience sympathy when she had a cancer scare in an early episode, but she quickly reverted back to her selfish behavior once she got the all-clear. Now battling significant weight gain, Betty redirected her wrath toward Don's "child bride," Megan, mainly because the new Mrs. Draper is younger, sexier and Sally's preferred female companion of late. In an attempt to drive a wedge between Don, Megan and Sally, Betty goes all middle school mean girl by casually mentioning to Sally that her dad had a "first wife" named Anna. But Betty learns she doesn't need to resort to childish games when it comes to her daughter's love. When Sally panics after getting her first period while away from home, she rushes back to Rye to seek comfort in her mother's embrace.
Ever since Roger lost the Lucky Strike account in Season Four, he has continued to wander around his professional and personal life in an aimless search for youth and relevance. The fifth season saw him with an empty appointment book, spurring him to pathetically horn in on Pete's business deals. His second marriage wasn't faring any better, as an eye-opening LSD trip – taken with his wife, Jane – only made the two realize how unhappy they were (their penchant for matching hot-pink towel turbans notwithstanding), and they separated soon afterward. After his brief detour into the valley of the twentysomethings, Roger turned his attention back onto someone more age-appropriate, Megan's mother, Marie Calvet. But even Marie wasn't interested in babying the infantile adman, declining his invitation to take LSD together. So Roger, having found yet another escape route from this thing we call life, closed out the season by dropping acid in a hotel room. Naked and alone.
To the casual observer, especially a female one in 1966, Megan Calvet Draper had hit the jackpot. In the span of one year, she went from SCDP receptionist to partner’s wife – receiving a considerable promotion to junior copywriter in the process. Her marriage to Don also garnered her a fabulous Park Avenue pad, a closetful of designer minidresses and an intimacy not previously awarded Betty: Don brought Megan up to speed on that whole Dick Whitman identity thing sometime between the engagement and their walk down the aisle. But wealth and nepotism still don't buy happiness. Midway through the season, Megan, despite an innate knack for the advertising game, decided to resume her previously nonexistent acting career. After a few months of failed auditions and a rejected screen test, Megan asked Don for a leg up, which she got in the form of a starring role in a Butler Shoes (a SCDP client) "Beauty and the Beast" commercial. As Don walked off the set and away from his dirndl-clad wife, his detachment suggested Megan's independence and success could lead to the downfall of their marriage.
Oh, Sally. This poor kid can't find a comfort zone no matter where she goes. If she stays in Rye, she gets to be verbally abused by Betty and drugged with Seconal by her demented step-grandma Pauline Francis. If she goes to New York, sure, her new BFF Megan will outfit her in the latest adolescent mod wear, but there’s also the chance of Sally witnessing her other step-grandma, Marie, give Roger a blow job at an advertising gala. The budding teenager is still carrying on her illicit relationship with her kinda-sorta-but-not-really boyfriend, Glen Bishop, now a prep-school student at Hotchkiss, but it wasn’t until the penultimate episode that they moved beyond late-night telephone calls. On the most unromantic date ever at the Museum of Natural History, puberty struck in the bathroom, and a go-go-booted Sally ditched Glen for a hot water bottle and some mother-daughter bonding with Betty.
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