The 20 best Mad Men episodes

Mad Men: 20 best episodes

Shut the door, have a seat: On July 19, 2007, Matthew Weiner's Mad Men premiered on AMC, introducing the world to Don Draper, the booze-soaked, ad wizard with a secret life and knack for turns of phrase ("That's what the money's for!"; "I don't think about you at all."; "Happiness is the moment before you need more happiness."). Across seven seasons, the Emmy-winning series helped create another peak in the era of Peak TV, turned cast members Jon Hamm (playing the aforementioned Don Draper), Elisabeth Moss (Don's secretary–turned–eventual copy chief, Peggy Olson), Alison Brie (frustrated housewife Trudy Campbell), January Jones (Don's vengeful ex-wife Betty), and Christina Hendricks (Sterling Cooper's office manager, and later partner, Joan Holloway) into household names, and left an indelible mark on the cultural landscape. To celebrate 10 years of Mad Men, let's revisit the show's 20 best episodes.

20. "Christmas Waltz," Season 5, Ep. 10

Even set-up episodes of Mad Men can be a priceless gift. "Christmas Waltz," a late season 5 outing, sets the stage for saga-turning events, including Lane Pryce's (Jared Harris) desperate suicide and Joan's degrading trick to land the Jaguar account. A clever script reminds us that not all presents are given with cheerful or sincere hearts. Lane, needing to pay off a large tax bill, steals from the company, hiding the theft via a scheme involving holiday bonuses that ultimately backfires on him. Harry (Rich Sommer) reneges on a promise to slip Paul's (Michael Gladis) crappy Star Trek spec script ("The Negron Complex") to NBC, but gives him cash to chase his Hollywood dreams after having sex with Paul's Hare Krishna girlfriend (a "gift" she gives Harry to blackmail him into staying away from Paul). And in perhaps the episode's most memorable, genuinely charitable storyline, Don treats Joan to a faux date test driving Jaguars after Greg (Sam Page) bums her out with a lump of coal in her stocking (i.e., divorce papers), a merry bit of business that culminates at a bar with friendly flirting and a discussion about why they never hooked up. Don: "You scared the s--- out of me!" —Jeff Jensen

19. "You Only Live Twice (The Phantom)," Season 5, Ep. 13

They haunt Don, the phantoms. There's the ghost of Lane Pryce, his suicide lingering in the office—and the ghost of Adam Whitman (Jay Paulson), another death-by-hanging. The haunting is physical: Don's tooth won't stop aching. And the haunting is romantic, too: In one of Mad Men's single most beautiful images, Don watches Megan's (Jessica Paré) screen test and seems to remember what it felt like falling in love with her. "The Phantom" isn't all doom and gloom: The SCDP (Sterling Cooper Draper Pryce) partners investigate more office space upstairs, pondering an expansionist future. But by the end of "The Phantom," Don is right back where we found him in 1960: Ordering a drink at a bar, meeting an attractive woman who definitely isn't his wife. At the start of the decade, Don was the vision of masculine cool: Maybe he's a phantom now, too. —Darren Franich

18. "The Jet Set," Season 2, Ep. 11

Dreamy Mad Men is divisive Mad Men, and it doesn't get much dreamier or more divisive than Don's surreal interlude with SoCal-Euro aristo-expats. "Jet Set" is the show's first Los Angeles episode, and it establishes the show's treatment of the West Coast as a sunbaked paradise-purgatory, a nowhere-place where Don's Manhattan cool gets burned away. There are great moments back in New York, too: Out-of-the-closet homosexuality arrives at Sterling Cooper, and Duck Phillips (Mark Moses) makes a power move with The British Guys. But the best moments of "Jet Set" are Don's woozy adventures in Palm Springs. He's sleeping with a girl named Joy who reads The Sound and the Fury: If nothing else, "Jet Set" is the episode for English majors. —Darren Franich

17. "Babylon," Season 1, Ep. 6

If the sexist atmosphere of Mad Men was mildly quaint, "Babylon" is the episode where the reality of the 1960s' chauvinistic attitudes turned grotesque. Roger (John Slattery) wants to keep Joan caged up like a little bird for afternoon delights, Betty is celebrating Mother's Day blissfully naïve of Don's extramarital affairs, and the office is a segregated caste system where a woman coming up with a great idea—as Peggy does for Belle Jolie lipstick—is compared to a dog playing a piano. "There's this great scene with the guys all on one side of a two-way mirror and the girls on the other [trying on lipstick]," says Christina Hendricks. "And it just sort of set up to me the dynamic of how the office is going to be for the rest of the show." —Jeff Labrecque

16. "Shoot," Season 1, Ep. 9

Just like Sterling Cooper, Mad Men has plenty of fantasies to sell, and the biggest one is the American myth of the self-made man, born disadvantaged like Don Draper, but able to become whomever he wants through sheer hard work. The saddest thing about that ideal? There's no equivalent for women, and no episode explores Betty Draper's heartbreak over that double standard better than this one. For the first time, we get to see Betty as a former model with a bright career ahead of her, now trapped in the same dead-end housewife track as her mother, doomed to vent her frustration at the neighbor's pigeons. She might look like a classic Hitchcock blonde in the final scene, head cocked up toward the birds in the sky, but she's no victim. This is Betty taking control in the only way she can. She's just a pretty bird in a cage herself, and those pigeons are free. No wonder she picks up that gun and shoots them. —Melissa Maerz

15. "Beautiful Girls," Season 4, Ep. 9

The show's title has always been a bit misleading. Mad Men is just as interested in exploring the gap between the interior and exterior lives of its female characters as that of their male counterparts, so this episode isn't exactly a uniquely distaff hour so much as an elegiac state-of-the-union for some of the series' best characters. Three professional women from the latest generation (Peggy, Joan, and Faye—the latter played by Cara Buono) get into an elevator going to the lobby, while one from the previous generation (Randee Heller's Mrs. Blankenship) gets into one going to the great secretarial pool in the sky. —Keith Staskiewicz

14. "Favors," Season 6, Ep. 11

For a second, try to forget about Pete Campbell (Vincent Kartheiser) and Bob Benson (James Wolk), as well as Peggy Olson and Ted Chaough (Kevin Rahm). All have crucial moments in "Favors," none of which come close to the tragic unraveling of Don's relationship with Sally, sparked when she discovers her father having sex with neighbor Sylvia Rosen (Linda Cardellini). Jon Hamm and Kiernan Shipka play their scenes with magnetic precision: Sally's frenzied crush for Sylvia's son morphing into frozen horror when she sees Don in the act. Don's glassy-eyed confusion when he realizes what has transpired. In another episode—or another drama—Bob Benson's advances toward Pete would've been a season highlight. So would have the post-pitch drinks Ted shares with Peggy and Pete, where the latter two resolve the ill will that has lingered since Mad Men's earliest episodes. But "Favors" is Don and Sally's story, and lays the framework for their relationship in the final season. —Eric Renner Brown

13. "Waterloo," Season 7, Ep. 7

Don Draper's days with the firm might be numbered if Cutler had his way, but it's Bert Cooper (Robert Morse) who bids adieu just as the Apollo astronauts walk on the moon. Peggy, Don, and Pete are one happy family during the victorious Burger Chef pitch, but this is Roger's episode. Chastised and condescended to by his mentor, he engineers a corporate sale to rival McCann that salvages Don's job and makes all the partners rich. Don's exile is over, but the ghost of Bert sings to him in a surreal Broadway dance number, "The Best Things in Life Are Free." It's a blessing. And perhaps a warning. After all, "No man has ever come back from leave. Even Napoleon." —Jeff Labrecque

12. "Tomorrowland," Season 4, Ep. 13

For all the joy Mad Men brings its viewers, it rarely deals in optimism. The takeaway from "Tomorrowland," then, is Don's engagement to Megan and all that it seemingly represents for the troubled ad-man. Previous (and future) finales ended on notes of deceit, infidelity, or at least uncertainty; "Tomorrowland" finds Don on a literal trip to Disneyland. He also receives Anna Draper's wedding ring and helps Betty move out of the family's Ossining house, making relative peace with his ex-wife in the process. But "Tomorrowland" belongs in the Mad Men canon because it's the bait in Weiner's greatest bait-and-switch. Although the episode hints at feminine marginalization to come—Betty's apparent second marriage malaise, Don's personal news trumping Peggy's professional success—it erects a series of high points to lend the tragedies in subsequent seasons even greater weight. —Eric Renner Brown

11. "Maidenform," Season 2, Ep. 6

"Women want to see themselves the way men see them," Paul says, explaining the appeal of the Playtex ad that divides all women into Jackie Os or Marilyn Monroes. But as Don Draper knows, having watched Sally give him a hero-worship gaze, he doesn't deserve, men want to see themselves the way women see them, too. If this episode offers smart commentary about the impossible ideas that women like Peggy and Joan and Betty must live up to, it's best when it shows how angry men get when they're forced into the same boxes—when, say, Bobbie (Melinda McGraw) tells Don that he has a reputation in bed, just like Marilyn did. Yes, it's a hollow victory for Peggy when she's forced to wear a low-cut outfit and join the male executives at a strip club. But, really, they're all Marilyns there, always submissive to the client, and sex is the best thing they've got to sell. —Melissa Maerz

10. "Signal 30," Season 5, Ep. 5

Pity Pete Campbell. Sure, he's the office's resident weasel, his face at all times either pickled with a supercilious sneer or smeared with sycophancy. But as "Signal 30" makes clear, he's also a shivering bundle of frustrations and inadequacies. If Don's the Mozart of masculinity, Pete is his Salieri, and when he's shown up by Don's ability to fix a faucet in his own house, it sends him into a shame spiral that culminates with Lane knocking him out in the conference room using Marquess of Queensberry rules. It's a bitter but empathetic portrait made even better by a parallel plot about Pete's glass half-full counterpart, Ken Cosgrove (Aaron Staton), and his quest for personal fulfillment through sci-fi fiction. —Keith Staskiewicz

9. "The Crash," Season 6, Ep. 8

The episode begins with a car crash—and largely concerns itself with the team trying to crash a campaign for Chevy over the course of a weekend—but the title primarily refers to Don's head-on collision with his subconscious which leaves him plummeting in free-fall like a stock market on Black Thursday. When the firm gets its own resident Dr. Feelgood to administer shots of vitamin A (for amphetamine), he actually ends up injecting twenty cc's of dream logic into the show's central nervous system, sending us (and Don) on a hallucinogenic pseudo-Lynchian nightmare ride as his past mixes with his present, an intruder gets into his apartment while his kids are there, and an injured Ken Cosgrove tap dances like a maniac. —Keith Staskiewicz

8. "The Strategy," Season 7, Ep. 6

A bit of a spiritual successor to "The Suitcase," this seventh-season episode again examines the working relationship between Peggy and Don as they try to pinpoint a new campaign. By now, Peggy is long gone from a mentee, but she's still wilting in Don's shadow, while Don has changed since they hashed out Samsonite. He eventually admits to her, "I worry about a lot of things, but I don't worry about you," before taking her hand and dancing to that anthem of self-reliance (and/or recalcitrance), "My Way." It's a sublime moment that shows how their relationship has evolved over time, only matched by the episode's final shot through the window of a Burger Chef of Don, Peggy, and Pete breaking bread, a living Edward Hopper painting of a very non-traditional family. —Keith Staskiewicz

7. "Commissions & Fees," Season 5, Ep. 12

7. “Commissions & Fees” Season 5, Episode 12 — Ron Jaffe/AMC

Death had patiently stalked Mad Men for five seasons, nibbling only at the edges, before it finally grabbed poor Lane Pryce around the neck. His suicide—following a comically botched attempt to die in his faulty new Jaguar—was pathetic (but almost endearing) and his failure to grab some notion of happiness marked the episode's theme. "Everything you think's going to make you happy, just turns to crap," laments wise teenage soul, Glen (Marten Holden Weiner, son of show creator Matthew Weiner), while Don dares Dow to think bigger: "What is happiness? It's a moment before you need more happiness." "It's actually one of the most quoted scenes in the show—that insatiability of their desire for success," says Matthew Weiner. "And that in contrast to the fact that this man [Lane] has never gotten what he needed." —Jeff Labrecque

6. "Meditations in an Emergency," Season 2, Ep. 13

6. “Meditations in an Emergency” Season 2, Episode 13 — Carin Baer/AMC

Everyone is waiting to see which side blinks first as the Cuban Missile Crisis unfolds, and that political setting seeps into the showdown between Don and Duck, who's arranged the merger that will diminish his rival. The threat of global annihilation pushes people to odd and revealing actions: pregnant Betty has sex with a stranger, Pete exhibits his first real traces of maturity, and then Peggy knocks the wind out of him by rejecting his affection with her confession about their baby. "By saying basically, the way that I felt about you was very true and did happen, but then it went away—who hasn't had that experience?" says Elisabeth Moss. "Being able to put into words such a vague emotion is what made our show different from anything else." —Jeff Labrecque

5. "Shut the Door. Have a Seat." Season 3, Ep. 13

Divorce looms large over Don in the season 3 finale—one at home and one at the office—and he's willing to fight hard for only one of them. "I said, 'Let's do The Magnificent Seven,'" says Weiner, referring to Don's scheme to quit the agency before it can be sold again, establishing a new shop with only the essential people. "They're going to be up against the wall, and they're going to have to gather all the players together. Everybody has to have a special skill, a special reason for being there." Don's humbling attempt to recruit a reluctant Peggy—"I will spend the rest of my life trying to hire you"—adds another rich layer to their relationship, while his vicious confrontation with Betty irrevocably breaks the vessel of their marriage. —Jeff Labrecque

4. "The Wheel" Season 1, Ep. 13

What makes this season finale so gripping isn't that Don makes the best pitch in Sterling Cooper history, selling Kodak's corporate drones on the mushy idea that their family-photo slide projector is "a time machine [that] takes us to a place where we ache to go again… to a place where we know we are loved." It's that Don sells this pitch to the world's biggest cynic: himself. It makes him rush home to his family—only to find an empty house—which only reinforces the reason why nostalgia is powerful: you can't go back to that place once it's gone. There are other heartbreaking moments: Betty's conversation with Glen, Peggy's refusal to look at her newborn baby. But the pitch stands out because those photos of a young family's happier days sum up what makes Mad Men great. It's not just the Carousel that's the time capsule, taking us to a place where we ache to go again. It's this show. —Melissa Maerz

3. "The Other Woman" Season 5, Ep. 11

Watching Peggy prove herself to the boys' club at Sterling Draper Cooper Pryce is so satisfying from a 21st century perspective, it's easy to forget that the late '60s weren't so liberating for every woman. This episode is a brutal reminder, as three smart, aspirational ladies are treated like "something beautiful you can truly own," to quote Ginsberg's (Ben Feldman) Jaguar tagline. Joan trades a one-night stand for a partnership. Casting agents force Megan to model her body like a sports car. When Peggy complains of unfair conditions at work, Don literally throws money at her. It's a devastating look at the real-world effects of objectification in the media, as well as a clever message about the catch-22 of advertising: There's nothing in the world that isn't for sale. And yet, what the agency's really selling—a feeling, an experience, a sense of freedom—is something that money can't buy. —Melissa Maerz

2. "Smoke Gets In Your Eyes," Season 1, Ep. 1

The potent evocation of midcentury America, the alluring ad agency world of Sterling Cooper, and the mystery of Don Draper (self-made success on the outside, dangerously hollow at heart) slowly reveals itself over Mad Men's sublimely crafted first hour. It's something of a day-in-the-life odyssey, tracking Don the smoke-blowing genius and Lothario at his most magical and toxic (turning cigarettes into near-sexy edibles with the tagline "It's toasted."), his most seductive and cynical ("What you call love was invented by guys like me. To sell nylons.") It's a brilliantly constructed hour long ironic joke that builds to a devastating punchline: Dazzlingly shallow, nihilistic Don is just a guy like us—married, with children, living in the burbs—aching for truer, deeper meaning. —Jeff Jensen

1. "The Suitcase," Season 4, Ep. 7

Don Draper, at the lowest point of a self-degrading downward spiral, forces Peggy to spend the night with him. Not like that! They have to brainstorm an ad for Samsonite, though what they end up doing is helping each other unpack the troubled baggage in Mad Men's finest hour. This is the episode that famously gave us Don's rejoinder to Peggy's demand for respect—"That's what the money's for!"—but it's just one carefully written, deeply felt moment in an hour stuffed with long, artfully crafted, high impact scenes, culminating in a scene of powerful quiet: Don grasping Peggy's hand, conferring deep gratitude and affirmation. A concentrated blast of brilliance from Mad Men's MVP players—writer Matthew Weiner, Jon Hamm and Elisabeth Moss—maximized by the delicate direction of Jennifer Getzinger. —Jeff Jensen