Meet Don Draper. Madison Avenue hotshot, Eisenhower-era self-made man. Real name: Dick Whitman. He swiped the Draper ID from a dead soldier during the Korean War to escape his painful country-poor past. Who knows his secret? Not his boozing, chain-smoking colleagues at ad agency Sterling Cooper. Not his model–turned–unfulfilled wife, Betty. Not his mistresses. Leveraging keen insights into human nature, the philosophizing flimflam man creates winning campaigns for Eastman Kodak and top client Lucky Strike. He clashes with Pete, a hungry young account exec who learns Don’s true identity and tries (unsuccessfully) to blackmail him in order to score a promotion. Don’s secretary, Peggy — an earnest striver — sleeps with Pete and spars with Joan, the imperious bombshell office manager engaged in a nowhere-bound affair with heart-attack-prone agency honcho Roger Sterling. Peggy gets promoted to junior copywriter — and gives birth to Pete’s baby after a pregnancy she hid from everyone, and didn’t even admit to herself.
Best Episode ”Smoke Gets in Your Eyes,” the instant-classic pilot, masterfully drew us into its richly realized vision of late-’50s/early-’60s America and the layered mystery of Don Draper.
It’s 1962. The Cold War is about to blaze hot. Don clashes with accounts chief Duck Phillips over recruiting younger talent and pursuing bigger clients. Peggy — who gave Pete’s baby up for adoption — returns to work, befriends a priest, and cuts her hair. Pete deals with his father’s death and the manhood-undermining revelation that fertility-challenged wife Trudy can’t give him children. Joan gets engaged to Greg, an insecure doctor, and stays with him after he drunkenly rapes her. Betty kicks Don out when she realizes that he’s been sleeping with the wife of a caustic potato-chip-shilling comedian. Don suffers an existential meltdown during an L.A. business trip and resolves to become a better man following a restorative idyll with the “real” Don Draper’s wife, Anna, whom he’s been supporting financially. Peggy finally tells Pete about the baby (and spurns his declaration of love); Don threatens to foil Duck’s power-grabbing plan to sell Sterling Cooper; and Betty, pregnant with Don’s third child, takes him back…after she has revenge sex with a stranger.
Best Episode ”The Jet Set” — a risky, rewarding mold-breaker — saw an increasingly unsettled Don running away to Palm Springs with a band of rich, pretentious nomads. (Going west seems to inspire rashness in Don — see: season 4.)
1963. The end of Kennedy’s Camelot is nigh. A British firm now owns Sterling Cooper, but Duck is gone, and Englishman Lane Pryce is now on board. Don struggles to remain faithful to Betty but succumbs to an affair with his daughter’s teacher. Art director (and closeted homosexual) Sal Romano rejects the advances of scuzzy Lucky Strike scion Lee Garner Jr., who retaliates by having him fired. Joan quits the agency to play housewife for Greg but must find new work after he washes out as a surgeon; he subsequently joins the Army. Betty — romantically pursued by an older man, governor’s aide Henry Francis — is rocked by the death of her father, Gene, then rocks Don’s world by demanding that he spill his closely held Dick Whitman secrets. After learning that Sterling Cooper is about to be sold, Lane conspires with Don and company to start a new agency. More new beginnings await, even for Betty: Don grants her a divorce, and she and their baby, Gene, fly with Henry to Reno, eager to start their (happy?) life together.
Best Episode ”Guy Walks Into an Advertising Agency” — also known as ”The Totally Hilarious One Where That Secretary Drives Over the British Guy’s Foot With a Lawn Mower.”
1964 gives way to 1965. ”(I Can’t Get No) Satisfaction” is on the radio, and the folks at Sterling Cooper Draper Pryce can relate. Don wins a Clio for a floor-wax ad. But he’s drinking more heavily than usual and bickering with Betty over how to deal with their despairing, daddy-favoring daughter, Sally. When he finds out that Anna has died, Don hits somewhere close to bottom. Introspection, sobriety, and a healthy romance with research expert Faye Miller follow. Meanwhile, Betty squabbles with Henry over her harsh parenting; Peggy begins hitting the counterculture scene; and Joan — lonely and afraid for Vietnam-bound Greg — has sex with Roger, gets pregnant, and comes thisclose to having an abortion. The fragile agency’s fortunes take a potentially calamitous turn when Lucky Strike — its lifeblood — pulls the plug. As the agency scrambles for new biz (points to Peggy for scoring the panty-hose account), Don lays off staff…and then, following another fateful West Coast business trip, impulsively proposes to his hot, great-with-kids secretary, Megan. A mad man indeed.
Best Episode ”The Suitcase.” Downward-spiraling Don and birthday girl Peggy stay up all night together working, sparring, grieving, and drawing closer. Mad Men‘s greatest hour — so far.