Mad Men returns for a sixth season this weekend on AMC, and even those of us who haven’t seen a frame of the two-hour premiere are nonetheless ready to talk our heads off about what for years now has been a top contender for Best Show on Television. Join us as we relive some of our favorite moments from the past five seasons, in all their bourbon-pounding, chain-smoking, lawnmower-crashing, existential-crisis-having glory. (Obviously, a multitude of spoilers after the jump — you’ve been warned.)

“One minute you’re on top of the world, the next minute some secretary is running you over with a lawnmower.”

Andy Greenwald: The beauty of Mad Men is that one can pick almost any scene to celebrate. The downsides of creator Matthew Weiner’s micromanaging are legendary and awful — just ask Kater Gordon how she’s enjoying the glow from her Emmy win — oh, that’s right, she lost her job — but the upsides are pretty hard to argue with. Every episode is a glittering jewel box of intricate character work with dialogue stronger than a vermouthless Manhattan and suffused with a warm, dreamy weirdness that separates it from everything else on television.

Anyway, that’s just a pretty way of saying this Hall of Fame totally paralyzed me. A single scene? From my favorite show? Not likely. And since Barnwell took Mrs. Blankenship, and the Ballad of Megan Not Crying Over Spilled Milkshake isn’t on YouTube, and we all sorta agreed to steer away from the biggies (sorry, Carousel; later, Suitcase), I’m left with choosing a moment that could be any moment. It’s not the best, but it’s as good as any other. In this one, Don shares the screen with Joan, an uncommon pairing, probably because the wise folks at AMC are worried about melting your flat-screen. An Englishman has just had his foot run over by a secretary drunk-driving a lawnmower. (The ’60s! You had to be there.) Don arrives because he’s supposed to, and Joan remains because of appearances, but neither of them can keep a lid on the laughter that’s been bubbling up beneath all the violence. And that’s before the English people show up to basically assign a man to the morgue merely because of what the lack of a foot is likely to do to his golf handicap. As always with Mad Men, it’s not the great clothes that make the show. It’s that one way or another — usually figuratively, this time literally — they always seem to end up spattered with blood.

Don Draper Makes Conrad Hilton an Old-Fashioned

Sean Fennessey: Don Draper’s drink of choice, when not suckling straight from that bottle of Canadian Club, is the old-fashioned. And when Mad Men became the subject of so many trend pieces and themed gatherings and absolutely depressing Halloween costumes, the attendant old-fashioned craze began in earnest. There were homemade video tutorials. There were unofficial recipes. And there was an officially endorsed cable network recipe. There were New York Times pseudo-histories. And there were bro-splaining blog posts about said pseudo-histories. (All those blog posts contained links to the true and official recipe of the cocktail in question.)

Here’s the thing about Don Draper’s old-fashioned: It’s a lot of salesman bullshit. After he hops over the bar like some running back scaling an overmatched safety, Draper pulls out two tumbler glasses. Good start. Then he drops in two sugar cubes. Important. That is followed by three drops of bitters — aromatic if you got ’em. He scoops some ice — a must — into a mixing glass. Then, in the absence of bourbon, Don splashes in a healthy pour of rye, an acceptable if uncommon substitute. He is on his way to a solid, if makeshift, old-fashioned. Then something horrible happens: Don Draper cracks open what appears to be a bottle of club soda and pours it into the mixing glass. Or is it a bottle of Evian? Doesn’t matter. Don has watered down the old-fashioned, a stunning turn. Then, continuing with this travesty unabated, he muddles the sugar in the tumbler and combines his elements into one solution for two imperfect drinks. You may be thinking, No big deal, the man’s at a party and he just happens to be shooting the breeze with an august hotel magnate. Lay off of Don. That would miss the point.

Don speaks a language of men. It’s not that that language is the right one or the decent one, but that’s his currency, particularly with an old San Antonio coot like Connie. They communicate with cocktails and in code. If this Hilton were properly rendered, he’d have slugged Draper in that lantern jaw for the watering-down. But it’s important to remember that Mad Men is a fantasy — a toxic concoction. And for a guy who’s swimming in it, Don Draper sure tends weak bar.

“I could have had you.”

Juliet Litman: When it comes to Mad Men‘s five season finales, there are plenty of iconic moments to talk about. Season 1 had Don’s “carousel” speech. Season 3 had the undeniable excitement of Sterling Cooper Draper Pryce’s stealth beginnings. Season 4 featured Don’s sudden engagement, and even the subpar (by Mad Men standards) Season 5 had most of the principals on the precipice of … something. But of the five finales, my favorite scene was from Season 2. Peggy finally reveals to Pete that she gave their baby up for adoption. Or to paraphrase Ms. Olson, she could have had him in her life forever, if she wanted that. The power of this scene is not in the major reveal, though at the time that aspect was thrilling. We’ve watched Peggy transform over five seasons, and underneath that evolution lies a fundamental, physical change that I somehow often forget about. The pregnancy wasn’t her choice, but giving up the baby and part of her self, followed by deciding to tell Pete about it (on a day they think they all might die because of missiles from Cuba), are the choices she made. Watching her explain it to Pete is like watching her tell her own origin story — the origin story that empowers her to leave SCDP. There are certainly other scenes that explain Peggy’s relationships (with people and the world) better, but I think this perfectly explains how Peggy sees herself and it unlocks the motivation behind much of what she has done since. Plus, Pete’s look of utter stupefaction has to rank very high in the Pete Campbell Bitchface Hall of Fame.

The Sterling Cooper Twist

Alex Pappademas: From Season 1’s thematically pivotal “The Hobo Code” — Don Draper’s down in the East Village with Midge and her beatnik friends, getting stoned, listening to Sketches of Spain, and experiencing Great Depression flashbacks; uptown, with Roger and Bert Cooper both away on business, the rest of Sterling Cooper cuts out early to drink and do the cha-cha at P.J. Clarke’s. When somebody drops “The Twist” on the jukebox, the room detonates with permission and possibility and communal joy; for at least the next minute or so, the music renders everything up for grabs, even emboldening Peggy to ask Pete to dance, like that’s going to happen. Meanwhile, downtown, the proto-hippies do a half-assed bunny-hop and then resume loafing. One of the points Mad Men keeps making is that it’s usually only clear in retrospect where the front lines of a culture war were. Here, Chubby Checker has never sounded more like the first shot of a revolution; Miles has never sounded so square.

A Day in the Life of Betty Draper

Katie Baker: Daytime kitchen cigs, divorcée/real estate gossip, sterling mothering … Betty Draper circa 1960 has the life I’ve always wanted.

Don Draper Fingerbang Threat Level: Hot Breath on a Taut Neck



Mark Lisanti: This is just a theory I’ve been kicking around for a couple of years, but do you think that maybe Don Draper has a problematic relationship with women?

I should have enough data by the end of Season 7 to arrive at some kind of answer. Don’t want to jump to any premature conclusions.

R.I.P., Ida Blankenship

Bill Barnwell: Miss Blankenship goes down as one of the all-time great six-episode bit characters, a comedic tour de force that became an integral part of Mad Men just long enough for people to start naming their cats after her. (Matt Weiner isn’t sorry about that, either.) Her demise (a stunt that the actress, the wonderful Randee Heller, performed herself) has some of the show’s best comedy, big and small. The slapstick stuff with Peggy and Pete is pretty wonderful, but there’s some even greater subtle stuff in there. The tiniest, most pitiful bit of incidental music that peeks in once Don realizes what’s happened is so funny, and it’s immediately topped by Don’s look of revulsion when Peggy suggests that they call an ambulance. Sadly, the subsequent eulogy from the partners afterward is missing from YouTube, but it includes that famous line from Bert Cooper: “She was born in 1898 in a barn. She died on the 37th floor of a skyscraper. She was an astronaut.” That also led to one of my favorite Photoshops of all time, by Grantland’s (and TBJ’s) own J.E. Skeets. Oh, and Miss Blankenship dying led to Megan becoming Don’s secretary and the main narrative thrust of the show occurring.

Joan vs. Peggy, Round 1

Steven Hyden: It’s not like it’s unusual to see Joan and Peggy occupy the same screen space. There they were together in the pilot, unicorn-from-outer space Joan playing mentor to poindexter-from-Jersey Peggy, advising her to make those pretty little ankles sing. Over the years, this teacher-student dynamic has remained pretty much intact, with Joan dispensing knowledge to her Padawan on everything from inter-office gender politics to the mating habits of upper-level ad executives to successful tips for recruiting a roommate. But the Joan-Peggy summit that sticks out most for me comes from the ninth episode of Season 1, previously known as the “You think you’re being helpful” scene, henceforth known as “Mad Men’s version of the De Niro—Pacino tête-à-tête in Heat.” Like all things Mad Men, the scene builds slowly, like a Jaguar campaign — Joan passive-aggressively suggests that Peggy cool it with the lunches, Peggy implies that Joan is threatened by her relatively rapid ascendancy to unpaid copy writer. Then the knives come out. First Peggy: “I know what men think of you. That you’re looking for a husband, and you’re fun, and not in that order.” Then Joan: “Peggy, this isn’t China. There’s no money in virginity.” “I’m not a virgin.” “No, of course you’re not.” (Insert sarcasm here.) The moment ends with an uneasy truce and an unspoken promise that if either of them gets in the other person’s way, sister, you are going down.

Lane vs. Pete, Round 38

Jonah Keri: Top 20 moments from this highly anticipated featherweight bout:

20. Pete tucking his tie in right before the fight.

19. Bert advising Don on the art of politics and warfare: “We don’t stop a war before an election.”

18. Bert massaging Roger’s shoulders, for some reason, while dishing out said advice.

17. “I’m FINE!” — No you’re not, Pete.

16. “Edwin’s wife, her life destroyed, called my wife with GO-ry details” — A show that had nothing other than Lane enunciating everyday household activities would be far more entertaining than, say, The Killing.

15. Everything about Joan and Peggy’s reaction. Especially when the lamp moves.

14. Pete, dismissively, to Lane, his face scrunched up with self-righteousness: “I was doing my job.”

13. The entire “Your account?!” insult string by Pete to Lane. I can count on one hand the number of times I’ve actually felt sympathy for Pete in the five seasons of this show. Every other Pete moment makes me want to punch the little weasel in his stupid, smug face.

12. Roger: “I don’t know about you two, but … I had Lane.”

11. “You want to take your teeth out, or you want me to knock them out?” — Pete’s false bravado = A+++++++

10. Pete, Don, and Roger’s uproarious reaction to the gum reveal.

9. “What, did she just … put it there and forget about it?” — Never change, Roger.

8. Pete’s look of terror after it becomes clear that he’s either going to have to fight Lane or lose whatever esteem he has left in the eyes of the other partners.

7. “You want some more, Mister TOAD?”

6. “Consider that … my last piece of advice.” — OH, NO YOU DIDN’T, LANE!

5. Roger: “I know cooler heads should prevail, but am I the only one who wants to see this?” — Thing is, we know Bert clearly doesn’t, and Don clearly does. This is a subtle fourth-wall moment, where Roger might as well be staring into the camera, pointing at all of us, and yelling, “FIGHT! FIGHT! FIGHT!”

4. Don closing the curtains. Can you imagine this scene playing out at your office today, only instead of breaking things up before any punches were thrown, one of the big bosses closes the curtains to ensure a private viewing party?

3. Roger popping a cig in his mouth just as the fight’s about to start. Roger is the best Mad Men character by a country mile, and I will fight anyone who disagrees (while insulting you with a British accent).

2. “NO. You’re a grimy little pimp.” — Distinctly remember pausing the DVR and cackling like a madman for a good five minutes the first time I heard this line.

1. “BECAUSE HE WAS CAUGHT WITH CHEWING GUM ON HIS PUBIS!”

Don Draper’s Palm Spraaangs Breeaaak

Emily Yoshida: Call me a coastist, but I think Mad Men is at its woozy best when it goes to California. For one thing, the show, which is shot on a soundstage just outside downtown L.A., can actually stretch its legs and shoot on location in Southern California. (Don wading into the ocean in San Pedro in “The Mountain King” was the first time that character really felt like more than a very expensive Ken doll to me.) No episode conveys the alternate reality of California in the ’60s more gorgeously and creepily than Season 2’s “The Jet Set,” a.k.a. when Don Draper accidentally walks into a David Lynch movie.

One of my biggest frustrations with Mad Men is that I often feel like it phones in emotions and lets the art department do the heavy lifting, but few episodes are more guilty of a mid-century fetish than “The Jet Set” and despite that, it’s still in my Top 5. There’s something both terrifying and telling about Don, already something of a phantom, being whisked off by a cabal of sunbathing hedonists who have themselves carved out new social identities in the arid freedom of Palm Desert, and physically breaking down in their presence. SoCal 101: Never drink anything given to you by a witchy woman in the desert, especially after she croaks that it’s “medicinal,” ESPECIALLY not while wearing a wool suit.

Also, that house makes me weak in the knees, obviously.

“The meaner you are, the more I like you.”

Brian Phillips: You probably don’t remember this. It had no bearing on any future plot. It wasn’t even one of the wow-ier moments of the episode it took place in, Season 1’s “Nixon vs. Kennedy,” which brought us not only the Real Don Draper, Blown-Up Korean War Guy flashback but also Bert’s withering “I don’t care,” “I literally can’t even hear you,” “If I were 10 years younger you’d have committed seppuku already” reaction to Pete exposing Don as a war deserter. Presidents were getting elected, a lot of big stuff was going on, and this scene just kind of floated in, like a feather on a current of gin vapor and illicit Republican office sex. You probably don’t remember this. It had no bearing on any future plot. It wasn’t even one of the wow-ier moments of the episode it took place in, Season 1’s “Nixon vs. Kennedy,” which brought us not only the Real Don Draper, Blown-Up Korean War Guy flashback but also Bert’s withering “I don’t care,” “I literally can’t even hear you,” “If I were 10 years younger you’d have committed seppuku already” reaction to Pete exposing Don as a war deserter. Presidents were getting elected, a lot of big stuff was going on, and this scene just kind of floated in, like a feather on a current of gin vapor and illicit Republican office sex. And that’s what’s so great about it. Mad Men has always seemed most itself when it clears out these little spaces between slabs of plot where it can linger on some seemingly extraneous human moment. That’s one reason why one of the show’s most distinctive modes is the late-night, soft-fog-of-alcohol comedown scene where the workday gloss comes off the characters’ identities and you sense that anything might happen. Maybe Harry kisses a secretary. Maybe somebody wrestles Duck Phillips. No show is flat better at convincing you that its scenes have reality’s leisurely open-endedness — that things are free to play out in whatever direction they happen to go. So here’s one of those moments. Kinsey and Joan don’t exist on the same plane either within the show’s world or within its dramatic hierarchy. In the world, Paul is a Princeton man; Joan is a secretary. In the drama, Joan matters; Paul exists to be bittersweetly mocked. But it’s the middle of the night. And for a couple of minutes, the hierarchies blur. They drop some of their normal defenses (not all: Look at the way she keeps her arm down while they’re dancing), and for a couple of minutes, they’re just two people. A world briefly swims into view in which Joan could possibly be sort of attracted to Paul and Paul could possibly sort of deserve it. Then it swims away again. It didn’t necessarily mean anything. Who hasn’t had nights like this? Don + Joan 4 Never Megan Creydt: Don and Joan have the most mature relationship on Mad Men, no contest. Yes, this scene smolders with an undercurrent of sex, but both of them know how badly that would end. You can tell there’s real love here, but Don respects Joan too much to try to seduce her (let alone marry her), and Joan sees Don too clearly to fall for him. She knows the minute they slept together she’d lose his respect, commit the sin of becoming familiar. Both of them are happy to keep the mystery alive, where Don can be Ali Khan and Joan can be the ideal woman on a pedestal. Roger and Jane’s Last Trip Michael Weinreb: Everything about Roger Sterling’s LSD trip feels pretty much like the apogee of televisual depictions of hallucinogenic experiences. But I might argue that this floor-bound, bathrobe-clad conversation between Roger and Jane is the most beautifully poetic two minutes of dialogue Matthew Weiner has ever given us. Peggy Gives Her Two Weeks Robert Mays: Typically, I turn to Mad Men for my weekly dose of dark, of which Season 5 certainly had its share. There are those moments, though, when the show isn’t busy trying to show us that we’re the worst, and for me, it’s been the relationship between Peggy and Don. The affection has been there from the start, and from Don’s “You’ll be shocked how much it never happened” advice to Peggy in the hospital to the classic “Suitcase” moment, it’s grown and changed in a way that any well-cast, complex television relationship ought to. Watching Peggy walk into Don’s office at the end of last season and give her notice seemed like a fitting end of that string. Also, I’m not sure I can remember a scene in this show when Jon Hamm is better. In these four minutes, he’s everything Don Draper is: caring, vindictive, petty, caring again, and finally, alone. If the kiss on the hand and the “Don’t be a stranger” don’t get you, you are made of straw. “At the Codfish Ball” (Datsik vs. Coldplay Remix) Molly Lambert: SALLY DRAPER + CREEPY GLEN BISHOP 4EVER (Dubstep Remix)

Filed Under: AMC, Mad Men, Television, Youtube Hall of Fame