The 30 Best ‘Mad Men’ Episodes

"Who is Don Draper?" When the reporter asks this question, Don drags on his cigarette. "I'm from the Midwest. We were taught it's not polite to talk about yourself." So welcome to the world of mystery man Don Draper, the Madison Avenue ad genius, a Roxy Music song in a suit. He's also Dick Whitman, a scam artist who stole his identity from a dead Korean War officer and built a new life out of lies. Everybody craves a chance to be Don Draper — especially Don Draper. (I always love how Rachel Menken's dad describes him: "A little dashing for my taste.") But behind the glam surface, he broods in his dingy bachelor pad, watching his own ads on late-night TV, hiring a hooker to come slap him around for Thanksgiving.

Best line: "So well built, we can't show you the second floor."—Don Draper

"Listen, Pete, I need you to go get a cardboard box. Put your things in it. Okay?" With these gentle words, Don finally gives that weasel Pete Campbell the axe, which feels long-awaited even though this is just the fourth episode of the series. Salty old patriarch Bert Cooper gives Don a lesson in how power operates: "Some people have no confidence in this country." It's Mad Men's first great Scary Bert scene, and definitely not the last.

Best line: "Your whole generation, you drink for the wrong reasons. My generation, we drink because it's good, because it feels better than unbuttoning your collar, because we deserve it. We drink because it's what men do."—Roger Sterling

Roger Sterling's daughter has her wedding — the day after November 22, 1963. No, it doesn't go well. The JFK news footage is chilling: Walter Cronkite fumbling with his glasses as he reads the death bulletin, the ominous reports about Adlai Stevenson and Gen. Edwin Walker in the background. The wedding guests sneak off to watch TV in the kitchen. Yet with so much tragedy in the air, Roger still manages to give the coolest wedding toast of all time.

Best line: "He was so handsome and now I'll never get to vote for him!"–Jane Siegel Sterling

Megan throws Don a surprise birthday party, complete with a sultry dance to "Zou Bisou Bisou." It's strange how Don and Betty, two of the rottenest spouses in TV history, luck into rebound marriages with the two sanest people on the show. (Henry and Megan really should have married each other.) Megan also decides to get Don's attention by cleaning the carpet in her lingerie. Shockingly, this plan works. No wonder we all got our delusional hopes up for this marriage.

Joan/Lane watch: A touching moment for us long-suffering Joan/Lane shippers, as Joan weeps in his office over her post-partum blues, and Lane cheers her up with a burlesque dance of his own.

Best line: "The only thing worse than not getting what you want is somebody else getting it."—Roger Sterling

A flashback to the Fifties: Roger meets Don in a fur store and gains a new best friend, i.e. an even more devious shark than he is. Meanwhile, in 1965, the Clio Awards inspire everybody to drink themselves into a Glo-Coated stupor, until Don wakes up to a few nasty surprises. Gentlemen, let's pace ourselves.

Best line: "You've crossed the border from lubricated to morose. Good night."—Joan Holloway Harris

Most of Season Two gets dragged down in piddly subplots: the Stand-Up Comedian (practically the only character on Mad Men who can't sell a joke), the Comedian's Wife (Don's least seductive seductress by a mile — somebody offer this lady a cough drop), Peggy's friend Father Creepy O'Eyebrows (the silliest one-man anthology of Hollywood Irish-priest cliches since M*A*S*H*'s Father Glasses McBoxing). But "The New Girl" has that stunning scene where Don visits Peggy in the hospital and gives her stern advice: "Get out of here and move forward. This never happened. It will shock you how much it never happened." Their whole strange relationship springs from this moment.


Best line: "I guess when you try to forget something, you have to forget everything."—Don Draper

A pivotal episode for the ever-horrific marriage of Don and Betty Draper. She confronts him about his past, leading to a long night of grief, tenderness, and regret. Plus a very confused schoolteacher waiting outside in the car. (The teacher still ranks No. 2 on the list of Don's Exes Most Likely to Reappear at His Door with a Butcher Knife. Faye is No. 1.) When Don and Betty go trick-or-treating with the kids, their neighbor asks, "Who are you supposed to be?" Neither one has an answer.

Best line: "Look at you, figuring out things for yourself."—Joan Holloway Harris

The Cuban Missile Crisis gets everybody scheming for the future, without knowing if the world will be still here on Monday. Duck makes his power move, bringing the new British bosses to the office. Betty makes her power move in a hotel cocktail lounge, as the radio plays "Stranger on the Shore."

Best line: "He never could hold his liquor."—St. John Powell 

Megan's parents visit New York to attend a banquet honoring Don, which means we meet Julia Ormond as the femme fatale Marie Calvet — c'est magnifique. Don wins an award that turns out to be as meaningless as every other prize on his shelf. And poor Sally, dressed up like Edie Sedgwick at the Factory, has a dinner date with yet another dashing father figure who disappears and lets her down. Go get 'em, tiger.

Best line: "Men don't take the time to end things. They ignore you until you insist on a declaration of hate."—Joan Holloway Harris

Sally runs away to visit Don at the office, which means awkward improvisations for the ladies in his life — Peggy, Joan, Megan and (especially) Dr. Faye. Peggy tangles with Abe, the most unbearable of her never-remotely-bearable boyfriends, with help from her lesbian pal Zosia Mamet. And there's a royal farewell for the Queen of Perversions. Bonus points for some Austin Powers-style bedroom banter: "Is it broken?" "The lamp?"

Best line: "She was born in 1898 in a barn. She died on the 37th floor of a skyscraper. She's an astronaut."—Bert Cooper

Peggy does research on the vibrating Relaxiciser belt, which teaches her a thing or two about feminine rejuvenation. Joan puts make-up on a sickly Roger, who gives her not quite the romantic speech of her dreams: "I'm so glad I got to roam those hillsides." And Don stars in the most insanely erotic five-second drinking scene in Mad Men history, knocking back a casual slug of Canadian Club right before his fateful one-on-one meeting with Bert. All his pheromones are popping when he strikes a pose to utter the words: "I accept."

Best line: "Peggy, the conversation of a raise is not inappropriate at this moment. But do not be timid. You presented like a man, now act like one."—Don Draper

Child actors are a loser bet — you gamble a family drama on them, you usually end up stuck with an A.J. or Meadow. How the hell did Mad Men get so lucky finding Kiernan Shipka to play Sally Draper? How did they know she'd turn into a real actress? After Sally gets a revelation about the dark side of Don Draper, the same thing Dick Whitman learned about his own father — a dishonest man lives here — she flees to prep school and spends a hilarious night putting her dad's sales expertise to work on the mean girls of Miss Porter's School.

Best song: The Monkees' "Porpoise Song," playing in Don's head as he curls up on the couch, a dirge for all the second chances he's blown.

Best line: "My father has never given me anything."—Sally Draper

The Red Wedding of Mad Men, at least in terms of laundry bills, as the fate of Sterling Cooper gets altered by a deus ex lawn mower. Admittedly, this episode is totally cheating in terms of the long-term story — Sterling Cooper's new bosses have a very bad Fourth of July, yet there are no recriminations. Nobody gets fired, not even that sad sack Lois. Ken Cosgrove, who brought the lawn mower to the office, gets promoted a few episodes later. The story never makes the Madison Avenue gossip rounds — it just never comes up again. My, those evil British overlords are forgiving! Or maybe, just maybe, this is a rare case of Mad Men playing fast and loose with the narrative to indulge some primal pulp thrills — and getting away with it.

Joan/Lane watch: A handshake in a hospital. Torture.

Best line: "I apologize for my wild imagination."—Bert Cooper

The milkshake that shook the world. The Season Four finale is easily the most controversial, divisive Mad Men twist ever, as Don takes the kids on a Disneyland vacation and returns engaged to the babysitter. It all comes down to one scene: When the Draper kids spill a milkshake at a diner, Don snarls, but Megan grabs napkins and says, "Don't get upset. It's just a milkshake." Don stares like she's from another planet. The kids look at each other in shock. You can see it on the faces of this miserable little family — everything's different now. A heartbreaker of a moment, and the milkshake epiphany makes Don suddenly decide to marry his foxy Montreal quicker-picker-upper. Another emotionally powerful scene: Don opens up to Sally about Dick, explaining, "That's my nickname sometimes." (And speaking of being a Dick — poor Faye.)

Pete Campbell, unlikely voice of social finesse: "You don't say 'congratulations' to the bride — you say 'best wishes.'" It's so depressing to agree with Pete Campbell about anything.

Best line: "Whatever could be on your mind?"—Joan Holloway Harris to Peggy Olson

All men have secrets, as a wise man once sang. Don is a man who's made of secrets — whether that means a beatnik girlfriend in the Village ("I want you to pull my hair and ravage me and leave me for dead") or a family photo burned to ashes in the wastebasket. Like Joan says, "Private…that's how these men are. And it's why we love them." But Don's darkest secret threatens to blow up when he gets a visitor from his previous life. His long-lost brother Adam shows up at the office, asking what everyone wants to know: "Who is Donald Draper?"

Best line: "I'd like to see more of it around here — people finishing things. I guarantee you that in the bottom drawer of every desk in this place is the first 10 pages of a novel."—Roger Sterling

Limit your exposure, indeed. Don and Sal take a business trip to Baltimore, where they find very different kinds of romantic adventure. Don gives Sal a lesson in the hobo code, as they spend a night pretending to be FBI agents. ("You ever heard of James Hoffa?") He also brings a souvenir home for his daughter — a stickpin from the uniform of the stewardess he just bedded. Don Draper, father of the year.

Best line: "Help yourself. Not the Stoli."—Roger Sterling to Pete Campbell

After a life spent trying to move forward, Don picks a spectacularly bad time to look back on his childhood, falling apart in the middle of his Hershey pitch. His life in ruins, he hits the road with his kids on a long Thanksgiving drive, then decides to pull over in Pennsylvania to show his daughter the whorehouse where he grew up. She raises an eyebrow at him. Then they stand there by the side of the road together, looking like a couple of lost kids, neither one with any idea what to say next.

Best song: Judy Collins' "Both Sides Now," which makes that final shot even more devastating.

Best line: "Well, aren't you lucky to have decisions."—Peggy Olson

We all knew the "somebody tries LSD" episode was coming, and we all knew the "Roger and Jane break up" episode was coming — but combining them was a typically brilliant Matthew Weiner curveball. While Roger swallows the sugarcube, Don and Megan take a different journey to Howard Johnsons, where the sherbet turns out to be a bad trip. Don hallucinates he's back on vacation in Disney's Tomorrowland, in the days when a milkshake was just a milkshake. And this whole episode gets even more psychedelic when you watch it synched up to Pink Floyd's Dark Side of the Moon.

Best song: The Beach Boys' "I Just Wasn't Made For These Times," a poignant soundtrack to Roger's acid trip. This is his happening and it freaks him out.

Best line: "I knew we were going someplace, and I didn't want it to be here."—Jane Siegel Sterling

Freddy Rumsen gets fired from Sterling Cooper for being a drunken mess, which is like Steven Adler getting kicked out of Guns N' Roses for doing too many drugs. Don and Roger send him off with one last bender, hitting an after-hours speakeasy casino. ("Is it Milwaukee?" "Yes, it is." "Son of a bitch.") But the night only reveals how desperately screwed up all three men are: Mike Moneybags, Dick Dollars and Tilden Katz.

Best line: "There's some incredible woman, and someone's going to end up with her, but it can't be you."—Roger Sterling 

Don wants to catch up on what the hip kids of 1966 are listening to, so Megan brings him the new Beatles album, Revolver. He drops the needle on "Tomorrow Never Knows," a blast of the future. He hates it. The Sterling Cooper world is a mess: Pete has floor sex with a self-destructive housewife after reading The Crying of Lot 49. (How far did Pete get into that book? Just curious.) Megan dumps a bowl of emotional Cool Whip in Peggy's lap. And Peggy ducks an unwanted phone call by picking up the receiver and yelling, "Pizza House!" It's kind of sweet how after all these years, Peggy is still so terrible at lying.

Best line: "I like the pictures of the earth! I find them to be majestic!"—Harry Crane

Hunter S. Thompson was right — the Kentucky Derby is decadent and depraved, at least when it involves Roger Sterling singing in blackface. Roger makes an ass of himself at his posh Derby Day soiree, but he isn't alone — over the course of a May weekend, everybody keeps giving musical performances that secretly reveal all their hidden emotional turmoil. (Just like the "Sirens" chapter of Ulysses.) Paul sings a stoned duet with his old pot-dealer pal from the Princeton Tigertones. Pete and Trudy do the Charleston. And Joan plays "C'est Magnifique" on the accordion for dinner guests, putting up a brave face even though she's just figured out her marriage is even more of a fraud than she realized.

Best line: "My name is Peggy Olson and I want to smoke some marijuana."—Peggy Olson

Don takes the California trip of his dreams, meeting a mysterious group of exiled European aristocrats who whisk him off to Palm Springs. Naturally, he breezes into their scene without even trying — they can't resist the sight of him sunbathing in his suit and hat. ("You look so comfortable alone by the pool all day.") And back on the East Coast, Peggy misses a Bob Dylan concert to get a haircut from her first gay boyfriend.

Best line: "My father will take care of you. He likes having you around. You're beautiful and you don't talk too much."—Joy to Don Draper

Don's finest moment as a salesman, pitching his idea for the Kodak Carousel — he gives a room full of strangers a tour through a life that isn't really his and a family he barely knows, getting sentimental over a childhood he never had. The man whose life goes in only one direction — forward — ponders what the word "nostalgia" means. Harry Crane isn't the only one who loses it at this speech. And just when you think you're all wrung out emotionally, it turns out there's one more scene left. Don't think twice, it's all right. Damn.

Best line: "This device isn't a spaceship. It's a time machine."—Don Draper

If you're a Bert Cooper fan, you're a fan of this episode — the old man demands Don's signature on a contract, unveiling the ruthless glare behind his genial smile. There's so much we never find out about Bert, a more bloodthirsty badass than Don or Roger will ever be. (When will we see his groovy sister Alice again?) But the sinister side of Bert "Beware the Non-Conformist" Cooper emerges when he wants something — like one of those moments in The Godfather when the aging Vito Corleone reminds everyone he's still the Don around here. The climax has to be the scariest Scary Bert scene ever.

Best song: Tennessee Ernie Ford's "Sixteen Tons," about the perils of owing your soul to the company store.

Best line: "Would you say I know something about you, Don?"—Bert Cooper

The first episode I saw, and the one that got me obsessed. Don's secret past comes to light, leading to a showdown in the office. Rachel Menken, who for some of us will always be the Don paramour who got away, asks him the question nobody else knows him well enough to ask: "What are you, 15 years old?" Don relives his harrowing war memories from Korea. And he meets the woman on the train, probably the first sympathetic female voice he ever heard, changing his life and giving him a lifelong thing for long-necked brunettes. Practically all his lovers resemble her somehow — with the notable exception of his wife Betty.

Best line: "You've got your whole life ahead of you. Forget that boy in the box. Look at you. Let me buy a soldier a drink."—The Train Woman

The most bizarrely upbeat Mad Men episode, which means it probably shouldn't count as a Mad Men episode at all. It's practically a caper movie: The Sterling Cooper crew hatch a scheme to break free from their British bosses and start their own agency. It's full of team-spirit comic camaraderie. (Besides the scenes where Don and Betty give their marriage those last few fatal clubs to the jaw.) When Roger announces, "Mrs. Harris, what a pleasure to see you," it's like she's Han Solo zooming in at the last minute to rescue Luke Skywalker. And Lane crowing "Very good, happy Christmas" on the phone is probably the giddiest moment of his life. Oh, Paul Kinsey — we feel your pain.

Best line: "I was going to tell you. No, I wasn't."—Roger Sterling

A few deeply damaged people spend the final days of 1964 together — Don heads out to California to visit Anna, then returns East for a weird New Year's adventure with Lane. They heckle a Japanese monster movie before meeting a couple of lady friends in the Village. So many painfully intimate moments: Don painting the living room with Anna, Joan throwing roses at Lane, Don slow-dancing to "Old Cape Cod" with Anna's proto-hippie Berkeley niece. This episode sums up what the Mad Men story is all about: Lonely people trying to take care of each other, and failing.

A casually prophetic aside from Joan: "I'll have Megan clean this up." Oh, there will be plenty of messes left behind for Megan to clean up.

Best line: "She does not go to Barnard."—Don Draper

Don smokes pot for the first time, getting high at Midge's Village pad, listening to Miles Davis with her boho pals. ("You're good with the words, man." "Well put.") He flashes back to his childhood encounter with the hobo, who taught young Dick Whitman the rules of the road — how to read strangers, how to mark your man, how to keep running away from trouble. Sal, the gay art director, could have used a similar tutorial in the arts of hobo Kabuki. But instead, he has an agonizingly sad dinner with the traveling salesman from Belle Jolie Lipstick.


Best song: Chubby Checker's "The Twist," which comes on the jukebox and turns Peggy into an American teenage rock & roll machine, even if she still makes you wonder why the hell she'd want to dance with Pete. And Joan somehow manages to steal the show shaking her hips to "Choo Choo Cha Cha."

Best line: "A dishonest man lives here."—the hobo

Lane finally blows his English cool and punches out Pete Campbell, a fantasy long shared by practically all Mad Men fans. This episode exposes the private agonies of these men, haunted by the miniature orchestras in their heads. Lane chases his cherished dream of being a real American, and takes it badly when the dream gets crushed. Ken writes science fiction. Pete pines for the Scarlett Johansson-esque high-school girl in his driving class. Roger charms the pants off yet another redhead ("Honey, I won't bore you with compliments") who will never be Joan. And Don sits at the whorehouse bar, drinking his bad memories away.

Joan/Lane watch: She gets up from the couch. She opens the door. She sits back down. What a killer moment.

Best line: "He was caught with chewing gum on his pubis!"—Lane Pryce

Let's go someplace darker. Don and Peggy pull an all-nighter, from office to diner to bar to office, in a two-person episode that captures all the obsessions of Mad Men: work as drug, work as sex, work as intimacy, work as escape from life, work as refuge from death. Work is for Don what alcohol is for Homer Simpson — the cause of and solution to all life's problems. Peggy finds out she's exactly like Don, like Rosalind Russell bonding with Cary Grant in His Girl Friday. It feels like they're the only two people awake in New York tonight, the only people who'll ever truly understand each other. If I had to watch one hour of TV for the rest of my life, it would be this one. There isn't a single 30-second stretch that isn't perfect. And at the end, Peggy leaves the door open.

Best line: "That's what the money's for."—Don Draper