Jon Hamm, Elisabeth Moss, Vincent Kartheiser, January Jones, Christina Hendricks, John Slattery
Regular airtime: Sundays, 9pm
It is 1960, and the historical event we move towards is the Kennedy/Nixon election. Much of this season is spent figuring out exactly where Don Draper came from. He cheats on Betty throughout, most notably with Midge (the Beat artist) and Rachel Menken (the Jewish department store owner), which Betty discovers in the season finale. We learn about Don (i.e., Dick Whitman) throughout flashbacks and his brother, who reemerges into Don’s life and later hangs himself.
When Pete discovers Don’s past (he took the identity of Don Draper, a man he served with in Korea), he threatens then attempts to blackmail him; upon learning the information, Bert Cooper famously remarks “who cares?” Oh yeah, and Peggy is unknowingly impregnated by Pete and, in a scene that perhaps inspired the series I Didn’t Know I Was Pregnant, gives birth.
It’s now 1962, and this is the season where Betty rides a bunch of horses. We move toward the Cuban Missile Crisis, and Don reads that Meditations in an Emergency book and runs away to California (to hang out with Anna, Dick Whitman’s wife). The season begins literally with the question “Who is Don Draper”, and of course he’s kind of awesome and kind of terrible. Don and Betty fight throughout, briefly separating before reconciling when Betty discovers she is pregnant (and has sex with that random guy in the bathroom). This is also the season where Peggy hangs out with priest Colin Hanks…
Not much time passes between seasons, though most of 1963 passes during the season. At the beginning of the season, Betty’s dad moves in before dying several episodes later, leading to the start of Sally’s emergence as a substantial(ly weird) character; meanwhile, Betty has feelings for Henry and Don has feelings for Sally’s teacher. This is my personal favorite season, as the office deals with the ramifications of being taken over by a British company and various awesome things happen throughout. This is the season where they bring in the British-Don-Draper who promptly has his foot run over by a lawnmower that somebody brings into the office.
The season ends with three of the series’ best episodes. In “The Gypsy and the Hobo”, Betty confronts Don his identity, which she discovers at the end of the previous episode. Set on Halloween, it is filled with great conversations about identity and disguises. In “The Grown-Ups”, the characters react to the JFK assassination, which unfolds surrounding the wedding of Roger’s daughter and the disintegration of Don and Betty’s marriage. Oh, yeah, and then “Shut the Door, Have a Seat” happens, where Weiner riffs on Ocean’s 11 as Don and co. steal a bunch of files and start their own company.
The fourth season picks up a year later, in late 1964 and moves through late 1965. Don’s new company struggles to get off its feet, as Don to redefine himself after his divorce. Anna is dying out in California, and her death unfolds during “The Suitcase”, that great episode where Don and Peggy hang out and work all night and talk about everything important to them and the series. Don starts a journal (at the request of Faye, remember her?, who is kind of awesome) and we maybe worry that the show is jumping the shark a little bit but it really just shows us that Don doesn’t have a clue what his deal is. And, shocker, Betty is still not happy.
Oh, and in the Season 4 finalé, “Tomorrowland”, Don goes to California with Megan and his kids, where they fall in love and spontaneously get engaged; Peggy brings in the first account since Roger lost Lucky Strike and Don vows in the New York Times not to represent any more tobacco companies; Joan is pregnant (surprise! she didn’t abort it!) with Roger’s baby, though her husband in Vietnam thinks it is his; while preparing to move, Betty fires Carla (who takes the blame when Sally is caught sneaking around with creepy Glen) and then fights with Henry about it, before learning about Don’s engagement ; and in the final scene, Don stares at the ceiling thinking about, well, everything…