The 10 Best Episodes of 'Mad Men'

Mad Men was a portrait of a different era that now feels like it's from a different era of its very medium, television. Matthew Weiner's AMC drama is an artifact of the days just before the streaming boom, when you had to wait an entire week for a new episode with only an extremely vague logline and an incomprehensible promo to keep you satiated.

That isn't to say that the series isn't extremely bingeable. It is, and is now available via Amazon Prime's Freevee. Yes, that means you can settle in with the saga of Don Draper (Jon Hamm) and the many faces of Sterling Cooper. Mad Men is a picture of mid-century white male malaise that at turns glorifies its chauvinistic hero and takes him down. It's as much the story of Elisabeth Moss' Peggy Olson's rise from secretary to creative force.

Here, we've compiled 10 of the most essential episodes in case you need a crash course or just want to check in with the hits.

Season 1, Episode 1
After working on sitcoms like The Naked Truth, Becker, and Andy Richter Controls the Universe, Matthew Weiner wrote the spec script for what would become the pilot of Mad Men, his workplace drama about the smoke-filled hallways of a Madison Avenue advertising firm in the '60s. The project didn't get made right away, but the pages impressed The Sopranos executive producer David Chase enough to bring Weiner aboard his incredibly popular and influential mob drama. Looking at the version of the Mad Men pilot that eventually got made after Weiner's run on HBO cut to black, you can see what Chase must've been drawn to: Supporting characters like Roger Sterling, Joan Holloway, and Pete Campbell emerge as fully formed comic creations, while the show's dueling protagonists, gruff creative Don Draper and ambitious secretary Peggy Olson, immediately draw you in with a potent combination of familiarity and mystery. From the slickly animated opening title sequence to the dagger-like final twist at the end—Don is married and has kids!—it's a suavely executed pitch that gets you hooked from the jump. —Dan Jackson

Season 1, Episode 8
Crucially, this episode introduces us to a young Dick Whitman through Don's drug induced-flashbacks after a night hanging out with his hippie lover Midge. But "The Hobo Code" largely excels as a Peggy episode. It opens with Peggy and Pete continuing their affair in his office early one morning, follows her through her triumph as Freddy Rumsen helps sell her copy, and ends with her disillusionment as Pete rejects her at P.J. Clarke's. "The Hobo Code" is a perfect meld of Mad Men's tendency toward existentialism mixed with its gleefully catty office politics. —Esther Zuckerman

Season 2, Episode 6
The "Jackie vs. Marilyn" dichotomy is maybe one of Sterling Cooper's greatest taglines, and this is one of the show's greatest episodes. Mad Men often commented on the sexism of the '60s male gaze, and "Maidenform" brings that to the fore as the firm works on a Playtex campaign over a Memorial Day weekend. Peggy is excluded from the "after hours" brainstorms, eventually giving herself a makeover to advance her career. Duck Phillips brings his kids to work and, feeling emasculated, abandons his poor, beautiful dog Chauncey. Don berates Betty for flaunting a bikini, all while banging Bobbie Barrett. It's all about men trying to define women for the purposes of advertising while feeling unable to handle their own emotions.  —EZ

Season 3, Episode 6
This episode will always be remembered as the one where someone runs over a guy's foot while riding a lawn mower through the office, but "Guy Walks Into an Advertising Agency" is also one of Mad Men's great Joan episodes. The hour chronicles the few days before the Fourth of July holiday, when Sterling Cooper's British partners Puttnam, Powell, and Lowe make a sudden visit to check on the state of the company. Joan's last day is on the horizon, and she's having a particularly hard time coping with the prospect of leaving. Don and the boys are stressing out about what PPL's visit means for their positions—it turns out that, while no one's jobs were lost in the restructuring, only Don got a promotion. Sally is terrified of baby Gene, who she thinks is somehow a reincarnation of her grandfather. Joan's husband Greg comes home drunk the night before her last day and announces he's been passed over as surgeon and she'll have to get a new job after all. During Joan's goodbye party, Lois careens the fateful lawn mower that Ken rode in on after he landed the John Deere account right over Brit Guy MacKendrick's foot. "That's life," says Joan as she and Don sit in the hospital's waiting room. "One minute you're on top of the world, the next minute some secretary's running you over with a lawn mower."  —Emma Stefansky

Season 4, Episode 7
Naturally, "The Suitcase" belonged on this list. Arguably the standout episode of the entire series, the one that makes it clear that the most important relationship in the entire show is the one between Peggy and Don. Not-quite-a-bottle episode, "The Suitcase" follows a long dark night of the soul as Peggy and Don skip the famed 1965 Sonny Liston and Muhammed Ali fight to work and hash out their issues. Don is supposed to be at the bout with Roger, while Peggy is supposed to be at a birthday dinner with her boyfriend Mark, who aimed to surprise her with the presence of her entire family. But at the last minute, Don asks her to go over the Samsonite account, forcing her to cancel and Mark to break up with her. Her anger leads to the famed "that's what the money is for" scene, where Peggy accuses Don of taking credit for her Glo-Coat campaign. That moment boils down the entire shows' ethos about creativity and capitalism, but it bleeds into something much softer as Peggy and Don proceed to get drunk. It all culminates with drunk Duck Phillips trying to take a shit in Roger's office and fight Don, but that results in Peggy cradling Don as he falls asleep on his couch. There he has a vision of Anna Draper and wakes up to learn that she has died. In the final beat, Don and Peggy grasp hands in the light of day, acknowledging their shared secrets and pain is devastatingly moving. —EZ

Season 5, Episode 5
For many viewers, Pete Campbell, the arrogant account executive played with a carefully calibrated sense of snivelling entitlement by Vincent Kartheiser, was Mad Men's most purely loathsome creation. But an episode like "Signal 30," which could also be titled "The One Where Lane Challenges Pete To a Fistfight in the Office and Beats His Ass," also underscores the character's unrelenting loneliness, self-pitying pain, and utter desperation. Co-written by Weiner and Cool Hand Luke screenwriter Frank Pierson, the episode features more than just the memorable image of Lane removing his coat and putting up his dukes to teach Pete a lesson in manners. There's the bizarre dinner party hosted at Pete's house, the surreal highway safety film that gives the episode its title, and the hilarious line about a man being "caught with chewing gum on his pubis." Throughout it all Pete emerges as an almost tragic figure, a man who can't fix the leaky sink in his house—and certainly can't fix his life. —DJ

Season 5, Episode 7
Yes, the one where Sally Draper walks in on Roger getting a blowjob from Megan Draper's mother. This is a Sally-heavy episode, one that further cements her disillusionment with her father and his cohorts. It opens as she complains to her old friend Glen about her life in the Francis household. She gets sent to Don's place after Henry's mother Pauline trips when Megan's bickering French parents come to visit. Megan is also a focus here as she negotiates her role as Don's wife and coworker. The new Mrs. Draper makes a key contribution to the Heinz Baked Beans campaign, essentially singlehandedly saving the account. But there's something gnawing at her, even with her success, indicated by her muted reaction despite Peggy's elation. By the end, everyone gathers in finery at the American Cancer Society dinner, with Don refusing to let Sally wear makeup. That adds insult to injury when the supposedly glamorous evening turns out to just be more of the same hideousness that she rejects. "How's the city?" Glen asks when Sally calls him later. "Dirty," she responds. —EZ

Season 7, Episode 6
Don spends this episode not-really-helping Peggy land SC&P a new client with her nuclear family-based pitch to Burger Chef. After joining the mile high club on the flight back to New York, Pete abandons Bonnie while he stays in Cos Cob to visit his daughter and buries himself in work, acting surprised when Bonnie gets fed up. She ditches him, flying back to L.A. on the same plane as Megan, who has been making trips to visit Don in the city. Bob bails GM exec Bill Hartley out of jail while a cop makes lewd references to their sexuality, and then proposes to Joan, who tells him, "You shouldn't be with a woman," and that she'd rather hope to find love for herself than make some arrangement with Bob. Peggy and Don spend an all-nighter hashing out strategies for the Burger Chef pitch, while Peggy confronts her anxieties about being unmarried at 30. Don counters with his own worries—"That I never did anything, and I don't have anyone." Peggy makes a breakthrough with her pitch, and she and Don share a dance as Frank Sinatra's "My Way" plays over the radio. The episode ends with Peggy, Don, and Pete sharing a "family table" at Burger Chef, where Don loyally defends Peggy's big idea. —ES

Season 7, Episode 12 
Say what you will about Mad Men's final season, but "Lost Horizon," a reference to James Hilton's 1933 utopia-set novel, was the lynchpin of the beginning of the end. It brought us the iconic image of Peggy power-strutting into the McCann Erickson office hungover with sunglasses on, a cigarette in her mouth, and Bert Cooper's phallic Japanese octopus painting cradled under her arm. (“You know I need to make men feel at ease!” Peggy says looking at the painting the night before in the gutted SC&P office, where she roller skated around the hallways and mustachioed Roger played the organ and both commiserated over a bottle of booze during their first real heart-to-heart. “Who told you that?” he says.) Joan frustratingly learns that McCann has no interest in making space for her and her client list, despite her partner status, through infuriatingly sexist meetings with her new coworkers, laying plain the overt misogyny that still infects offices today. ("Women love it here," a smug Jim Hobart tells Joan before she threatens him with a lawsuit involving the Equal Employment Opportunity Commission, the ACLU, and Betty Friedan, then cuts an unsatisfying buyout deal of her SC&P shares so she can get the hell out of there.) Which brings us to Don, McCann's "white whale," who's given the king's tour of his new office before settling into a large corporate meeting for the Miller Lite campaign. The process grinds on him; instead, he stares out the window, sees a plane flying overhead (feeding into the zany "Don is D.B. Cooper" conspiracy theory), and straight-up walks out of the office mid-meeting, and starts his long drive—with a pit stop in Wisconsin to try and locate his latest lover, Diana, and a hallucinated conversation between Don and the deceased Bert Cooper—to self-actualization while David Bowie's "Space Oddity" plays out the episode.
—Leanne Butkovic

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