The sixth season of Mad Men, when this piece originally ran, began with Roger Sterling facing the deaths of two of his loved ones: his mother and his shoe-shine man. The normally blithe executive showed some surprising introspection (and even broke down crying), but even in a state of ennui he still was able to do what we’ve counted on him doing for the previous five seasons: dole out some stellar quips. The first half of season seven ended with the death of his partner and mentor Bert Cooper. Even then he had a piece of off-the-cuff gold — “I should’ve known it was near the end. Every time an old man starts talking about Napoleon, you know they’re going to die.”
Between seasons four and five, Mad Men creator Matthew Weiner anthologized many of Roger Sterling’s best lines in a book, Sterling’s Gold. Named after Roger’s ill-fated memoir, Sterling’s Gold was full of Roger’s pithy, nihilist bile, but it left plenty of cutting quips on the cutting-room floor. So, in the interest of posterity, Vulture has compiled the authoritative canon.
Season One
“An ad man who doesn’t like to talk about himself? I think I may cry.” (season one, episode two)
“Psychiatry is just this year’s candy-pink stove.” (S1, E2)
“I think it behooves any man to toss all female troubles into the hands of a stranger.” (S1, E2)
“I’ll tell you what brilliance in advertising is: 99 cents. Somebody thought of that.” (S1, E3)
“I bet daily friendship with that bottle attracts more people to advertising than any salary you could dream of.” (S1, E4)
“Maybe every generation thinks the next one is the end of it all. Bet there are people in the Bible walking around, complaining about kids today.” (S1, E4)
“I’m glad everybody can make it sound like they’re working so hard.” (S1, E5)
“Look, we’ve got oysters Rockefeller, beef Wellington, napoleons. We leave this lunch alone, it’ll take over Europe.” (S1, E6)
“Reservations at home. I’ve had those. Easiest ones to break.” (S1, E7)
“When a man gets to a point in his life when his name’s on the building, he can get an unnatural sense of entitlement.” (S1, E7)
“At some point, we’ve all parked in the wrong garage.” (S1, E7)
(Waving an empty bottle) “Can something be done about this sadness?” (S1, E7)
“At some point [women] lose that. That glow of pure youth. It’s like they hit 30 and somebody puts out a light.” (S1, E7)
“I like redheads; their mouths are like a drop of strawberry jam in a glass of milk.” (S1, E7)
“You hear Pan Am, you imagine London, holed up at the Dorchester with three stewardesses. The truth is it’s more like a twenty-hour boomerang flight so you can make a coupon sing in Spanish.” (S1, E9)
“I’ve worked with a lot of men like you, and if you had to choose a place to die, it would be in the middle of a pitch.” (S1, E9)
“You know, Mona had a dream once where I hit the dog with a car. She was mad at me all day, and I never hit the dog. We don’t even have a dog.” (S1, E10)
“The day you sign a client is the day you start losing them.” (S1, E10)
“You know what my father used to say? Being with a client is like being in a marriage. Sometimes you get into it for the wrong reasons, and eventually, they hit you in the face.” (S1, E10)
(On the film The Apartment) “Oh, please. A white elevator operator? And a girl at that? I want to work at that place.” (S1, E10)
“It’s Labor Day weekend. Between now and Monday, we have to fall in love a dozen times.” (S1, E10)
“When God closes a door, he opens a dress.” (S1, E10)
“I feel like I should make a speech: Get back to work.” (S1, E11)
“I shall be both dog and pony.” (S1, E11)
Season Two
(Duck: “Got a second?” ) “Nothing good ever started with that sentence.” (S2, E1)
“Last time Freddy Rumsen had a cup of coffee, it was one of five being poured down his throat by a cop.” (S2, E1)
“It’s incredible what passes for heroism these days. I’d like ticker tape for pulling out of my driveway and going around the block three times.” (S2, E2)
“Can I just fire everyone?” (S2, E2)
“Jets are made for dropping bombs on Moscow, not French cuisine. Although I like those little girls they have. You know, they’re completely captive.” (S2, E2)
(Don: “What kind of company are we going to be?”) “The kind where everybody has a summer house?” (S2, E2)
“A guy like that must know how to make a charming apology, or he’d be dead.” (S2, E3)
“Nobody knows what I’m doing. It’s good for mystique.” (S2, E5)
“I’ll tell you what I told my daughter: If you put a penny in a jar every time you make love the first year of marriage, and then you take a penny out of the jar every time you make love in the second year, you know what you have? A jar full of pennies.” (S2, E5)
“Errol Flynn is gone, and so is my taste for swordplay.” (S2, E6)
“I’ve been married for twenty years. I know the difference between a spat and spending a month on the couch.” (S2, E6)
“Where did you get that sweater? I want to make sure my daughter never buys it.” (S2, E7)
“I’ll bet she suffers in silence out there, hoping you’ll notice her. Wait until she finds out about your Cadillac. She’ll be waiting naked right in front of this window.” (S2, E7)
“Not to get too deep before the cocktail hour, but do I need to remind you of the finite nature of life?” (S2, E7)
“I can see someone wanting to reprimand you seriously. But firing? Seems a little permanent.” (S2, E7)
(Introducing Duck Phillips and Crab Coulson) “Crab, Duck. Duck, Crab.” (S2, E8)
(To Freddy Rumsen) “There’s a line, Freddy. And you wet it.” (S2, E9)
(On Mrs. Cooper’s two-headed mink stole) “Alice. I’m sorry, I don’t know whose eyes to look at.” (S2, E12)
Season Three
“I have Stolichnaya and Cuban cigars. Sent them from Greece. Should’ve tried a pound of opium.” (S3, E1)
“I told him it was a stupid idea, but they don’t always get our inflection.” (S3, E1)
(On Lane’s suit of armor) “You ever get three sheets to the wind and try that thing on?” (S3, E2)
(On pregnant Betty) “Oh, look. Princess Grace just swallowed a basketball.” (S3, E2)
“It’s a mistake to be conspicuously happy. Some people don’t like it.” (S3, E3)
“Let me put it in account terms: Are you aware of the number of hand jobs I’m going to have to give?” (S3, E5)
“I don’t know if anybody’s ever told you that half the time, this business comes down to ‘I don’t like that guy.’” (S3, E5)
“My father was the tallest, handsomest, vainest man in New York, and he got his nails done. He had his fourth coronary behind the wheel and hit a tree. The windshield severed his arm, and he was dead, so they never put it back on. In the casket he had one hand. The nails were perfect.” (S3, E6)
(After the lawnmower accident) “Jesus, it’s like Iwo Jima out there. We should put a rubber mat down so Cooper can get around.” (S3, E6)
(Paul Kinsey: “He might lose his foot.”) “Right when he got it in the door.” (S3, E6)
(On the lawnmower incident.) “Believe me, somewhere in this business, this has happened before. (S3, E6)
“It’s called Confessions of an Ad Man. Please. It’s the book everybody writes, only he got it published. It should be called 1,000 Reasons I’m So Great.” (S3, E7)
(To Don) “What do you think Accounts does, besides limit your brilliance?” (S3, E9)
“Look, Annabelle, we were not in Casablanca. The only similarity is that you left me for another man. That woman got on the plane with a man who was going to end World War II, not run her father’s dog-food company.” (S3, E11)
(To Mona, regarding their daughter) “Tell the bride that everything is copacetic. We both agree that she’s nuts and she should shut up.” (S3, E12)
“Mona, you’re a lioness. And thank you for resisting the urge to eat your cub.” (S3, E12)
(About Jane, after Kennedy’s death) “She’s obsessed. It’s the most interest that girl’s ever had in a book depository.” (S3, E13)
“I know you’re sniffing around because I have a golden pork chop dangling from my neck.” (S3, E13)
“Have another. It’s 9:30, for God’s sake.” (S3, E13)
“Well, it’s official. Friday, December 13, 1963: Four guys shot their own legs off.” (S3, E13)
“Look, they still have a picture of Kennedy up. Although what are they going to do, take it down and put up Lyndon Johnson?” (S3, E13)
Season Four
“My uncle lost his leg hitching a trailer. He used to ask me to scratch his toes. He didn’t have any.” (S4, E1)
“A wooden leg! They’re so cheap, they can’t even afford a whole reporter.” (S4, E1)
“See her this weekend. You hit it off, come Turkey Day, maybe you can stuff her.” (S4, E1)
(On visiting businessmen) “I love how they sat there like a couple of choirboys. You know one of them is leaving New York with VD.” (S4, E1)
“You know, no one who’s ever been associated with an actual event has though it’s been portrayed honestly in the newspaper.” (S4, E1)
(On his monochrome office redesign) “Jane got a decorator. I feel like, with my hair, you can’t even see me in here.” (S4, E2)
“If Lee Garner Jr. wants three wise men flown in from Jerusalem, he gets it.” (S4, E2)
“I pity him, marooned in that sea of bikinis.” (S4, E2)
“My father used to say this is the greatest job in the world except for one thing: the clients.” (S4, E2)
“See, I would never buy a sailboat. I don’t want to do things myself. For that price, the boat should have a motor.” (S4, E4)
(On Secor Laxative’s decision to buy television ads) “How’d you ease them into it? Must’ve had to loosen them up first.” (S4, E5)
“Have a drink. It’ll make me look younger.” (S4, E5)
“I told him to be himself. That was pretty mean, I guess.” (S4, E6)
“I can’t say I know my furs that well. I know my mother had a chinchilla; I was always on the verge of a romantic relationship with it.” (S4, E6)
(Woman in bar: “Is that Don Draper? Is he attached?”) “To that glass? Absolutely.” (S4, E6)
“My mother always said, be careful what you wish for, because you’ll get it, and then people get jealous and try to take it away from you.” (S4, E6)
(Don: “I’ll buy you lunch.”) “I’m stuffed. I had a jar of olives.” (S4, E6)
(To Joan, at the Clio Awards) “So you’re really gonna leave me alone with all these naked gold women?” (S4, E6)
“I’m going to count to three, and then I’m gonna start saying a lot of words you don’t like, sweetheart.” (S4, E7)
(After hiring a masseuse for Joan) “I knew I was rubbing you the wrong way, so I thought, why not have someone rub you the right way?” (S4, E9)
(Joan: “I brought you bear claws.”) “Caroline won’t let me have one, unless it’s on the end of a real bear.” (S4, E9)
“Dammit, I don’t want to die in this office … If it looks like I’m going, open a window. I’d rather flatten the top of a cab.” (S4, E9)
(On Ida Blankenship) “She died like she lived: surrounded by the people she answered phones for.” (S4, E9)
“Well, I gotta go learn a bunch of people’s names before I fire them.” (S4, E12)
Season Five
“When you’re done with him, just fold him up and slide him under the door.” (S5, E1)
(Harry: “It’s a Steinway walking stick.”) “You could stick it up your ass and have a concert.” (S5, E1)
“Look at you, delivering drinks. We should get you a pair of roller skates.” (S5, E1)
“As a wise man once said, the only thing worse than not getting what you want is someone else getting it.” (S5, E1)
“She’s a great girl. They’re all great girls. At least until they want something.” (S5, E2)
(On the baby he fathered with Joan) “Oh no? He’s a loafer?” (S5, E2)
“Has anyone even seen this baby with you walking next to him?” (S5, E2)
“Is it just me, or is the lobby full of Negros?” (S5, E2)
“Baked beans and the Rolling Stones: a client’s idea if I ever heard one.” (S5, E3)
“I want you to bring me a good-looking version of Don.” (S5, E3)
“I had drinks with Mohawk. I sat down with two of them, and I swear by the end there were three.” (S5, E3)
“My wife likes fur, but you don’t see me growing a tail.” (S5, E5)
(On discovering that a Jaguar executive was caught with chewing gum “on his pubis”) “What, did she just put it there and forget about it?” (S5, E5)
(On Lane, challenging Pete to a fight) “I know cooler heads should prevail, but am I the only one who wants to see this?” (S5, E5)
“Did you ever hear the one about the farmer’s daughter? This is where it all takes place.” (S5, E6)
“Don, come on. Alone, I’m an escapee from some expensive mental institution.” (S5, E6)
“But the two of us are a couple of rich, handsome perverts.” (S5, E6)
“I’m supposed to have dinner with Jane’s snooty friends, sit around talking about Frank Lloyd Rice. I always say it that way. They hate it.” (S5, E6)
“Who knows why people in history did good things? For all we know, Jesus was trying to get the loaves and fishes account.” (S5, E7)
(Sally: “You’re wrecking the speeches.”) “You’re a mean drunk. You know that?” (S5, E7)
“Jane wanted a baby, but I thought, why do that to somebody?” (S5, E8)
“How Jewish are they? You know, Fiddler on the Roof: audience or cast?” (S5, E9)
“You know, it’s sacrilege to say this, but Pearl Harbor was an act of genius. The only thing they didn’t plan for was success. The Japs won and they didn’t know what to do with it.” (S5, E10)
“Are you gonna tell me what you’re going to talk about, or is my look of surprise part of the sales pitch?” (S5, E12)
(After Don’s meeting with Dow Corning) “I’ll buy you a drink if you wipe the blood off your mouth.” (S5, E12)
“Stop being demure. You’re already on the bed.” (S5, E13)
Season Six
(After Don returns from Hawaii) “Hello, Don Ho. You have a blue drink in the white sand? Ernest Borgnine chase you down the alleyway with a switchblade?” (S6, E1)
(Re: His mother’s funeral) “I looked out on that crowd, and all I saw was a bunch more women I disappointed.” (S6, E1)
“I’m afraid she left everything to the zoo. She’s making them name the animals … Her will looked like the manifest from Noah’s ark.” (S6, E1)
“You know, I used to jump off mountains, and it never occurred to me that I had this invisible parachute.” (S6, E1)
(To psychiatrist) “I’m just acknowledging that life, unlike this analysis, will eventually end, and someone else will get the bill.” (S6, E1)
“You know, we sold actual death for 25 years with Lucky Strike. You know how we did it? We ignored it.” (S6, E1)
“What are the events in life? It’s like, you see a door. The first time you come to it, you say, ‘Oh, what’s on the other side of the door?’ Then you open a few doors and then you say, ‘I think I want to go over a bridge this time. I’m tired of doors.’ Finally you go through one of these things, and you come out the other side, and you realize that’s all there are: doors! And windows and bridges and gates. And they all open the same way. And they all close behind you. Look, life is supposed to be a path, and you go along, and these things happen to you, and they’re supposed to change your direction, but it turns out that’s not true. Turns out the experiences are nothing. They’re just some pennies you pick up off the floor, stick in your pocket, and you’re just going in a straight line to you-know-where.” (S6, E1)
(On Don vomiting) “He was just saying what everybody else was thinking.” (S6, E2)
“I’m afraid she left everything to the zoo. She’s making them name the animals … Her will looked like a manifest from Noah’s Ark.” (S6, E2)
(On Don’s Sheraton Hawaii pitch) “What’s the matter? You didn’t get all your vomiting done at my mother’s funeral?” (S6, E2)
“That was the deftest self-immolation I’ve ever seen.” (S6, E3)
(On the MLK shooting) “The man knew how to talk. I don’t know why, but I thought that would save him.” (S6, E5)
“I’d live in my car if I could. You know, with her in the backseat navigating.” (S6, E6)
“Isn’t there a section of this meeting called ‘good news’?” (S6, E6)
“Remember Ken Cosgrove? Like a six-foot version of Alan Ladd?” (S6, E6)
(Burt Peterson: You’re a prick, you know that?) “Damn it, Burt, you stole my good-bye.” (S6, E6)
“Why don’t you take a nap? Your face looks like a bag of walnuts.” (S6, E8)
“They’re Lincoln Logs. Thought maybe he’d build his mother a house.” (S6, E9)
“Sunkist, Carnation, the avocado people: My biggest job in these meetings is to keep them from saying ‘golly’ too many times.” (S6, E11)
“Be slick. Be glib. Be you.” (S6, E11)
“We’re conquistadors. I’m Vasco de Gama and you’re … some other Mexican. We’re gonna land there, buy whatever they’ve got for the beads in our pockets. Our biggest challenge is to not get syphilis.” (S6, E11)
(Harry: It’s a dry heat.) “It’s a dry heave.” (S6, E11)
“Big accounts require a golf-and-dining offensive.” (S6, E11)
(Danny Siegel: I know these lugs from my days in advertising.) “More like a day, wasn’t it?” (S6, E11)
“What are you gonna do when you fail here, keep going west? Japan’s a long walk for those little legs.” (S6, E11)
“You know, I was a boxer. There’s nothing like finding that magic spot that’ll drop a man to his knees. You know, unless he’s already starting there.” (S6, E11)
“Are you tripping? I’ve done it five times. So if you’re trying to see through me, just know that I am this handsome and this rich.” (S6, E11)
(On his California trip) “It was a series of busts, and not the kind I like.” (S6, E11)
(On Ken Cosgrove) “I’d listen to the cyclops, Pete.” (S6, E12)
“Well you know what they say about Detroit: it’s all fun and games till they shoot you in the face.” (S6, E13)
(Bob: I assure you I’m not involved with Joan. We’re just buddies.) “Joan’s known for having a lot of buddies. They go fishing together.” (S6, E13)
Season Seven
(Toasting his daughter) “To the fear of an ambush.” (S7, E1)
“Well, the snow’s melted, but not the hearts of New Yorkers. I just had some old lady call me a kike.” (S7, E2)
“Sign them, right away. Sit in his yard with a pen if you have to.” (S7, E2)
“That’s a nice offer. They’re really trying to make it sound like it’s not a demotion.” (S7, E3)
(On hiring Don) “I guess you forgot I found you at the bottom of a fur box.” (S7, E3)
“You were a disaster. We did you a favor. The man who talked to Hershey? I’ve seen that man wandering the streets with a sandwich board saying ‘The end is near.’” (S7, E3)
“That’s my name on the door out there. This is my agency. I’m the president of this agency, I don’t have to ask anybody anything. You know what? I call a holiday for the whole office right now.” (S7, E3)
“We’re getting a computer. It’s gonna do lots of magical things, like make Harry Crane seem important.” (S7, E4)
(Mona: Margaret’s run away.) “To where? Bergdorf’s?” (S7, E4)
(After a hippie passes him a joint) “Now I see why we’re eating so early.” (S7, E4)
“With all the brainpower around here? I’m certain you’ll put a man on the roof.” (S7, E4)
(Jim Hobart: It’s run by morons.) “A lot of companies succeed that way. Look who I’m talking to.” (S7, E6)
(On rival firm McCann Erikson) “When we grow up, we’re gonna kill you and marry your wife.” (S7, E6)
“The New York Athletic Club frowns on people making advances in their steam room. I was kidding around, but — I think you’re making eyes at me. I’m gonna go get a massage and relieve some of this tension.” (S7, E6)
(Jim Cutler: Ah, good you’re still here.) “That’s your opinion.” (S7, E6)
“Did you see we landed on the moon? Neil Armstrong, what are you going to do with the rest of your life? Screw every girl in Florida, I guess.” (S7, E7)
“Poor Bert. I should’ve known it was near the end. Every time an old man starts talking about Napoleon, you know they’re going to die.” (S7, E7)
“Cutler’s not gonna stop until the firm is just Harry and the computer.” (S7, E7)
“We finally turned this place into a threat, and they’d like to neutralize it with cold, hard cash.” (S7, E7)
