Celebrating 40 Memorable 'Mad Men' Characters, Because We're Not Quite Ready To Say Goodbye

On Sunday, we'll say a fond farewell to the thoughtful, meaty, increasingly GIF-able drama series Mad Men . The 7-season-old show can effectively be described as one man's devolution from grandeur to oblivion... or wherever the heck else he'll end up. But, even though Mad Men is in fact Don Draper's story, we've met so many memorable characters over the years that we couldn't refrain from calling it a fantastic ensemble piece. Here are a few parting thoughts on 40 of our favorite (and least favorite... but altogether most memorable) Mad Men heroes, villains, and Rumsens.

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“If you don’t like what’s being said, change the conversation.”

Depending on who you ask, Don has been the focus of one of television’s meatiest character dissections or the purveyor of seven season’s worth of paralyzing monotony. Love him or hate him, Mad Men is Don’s story — that of a man plummeting slowly and erratically after a lifetime struggling to climb, of a man whose internal and external worlds make for the perfect recipe of self-destruction.

After a decade of occupational obsessions, extramarital affairs, and Kerouacian jaunts into the unknown, we’re finally called to say our goodbyes to Donald Draper, or Dick Whitman, or D.B. Cooper, or whatever you’ve decided to call him. So what does eternity have in store for Don?

Theorize all you want, but when has Matthew Weiner ever actually met our expectations with his sullen series hero?

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“I don’t think anyone wants to be one of a hundred colors in a box.”

How could Matthew Weiner induct a modern viewing audience into a world that is for all intents and purposes inhabited and run by aliens? Simply, by giving us Peggy: the human who wins a trip over from Earth (i.e., Brooklyn) and spends the rest of her days trying to live amongst the otherworldly beings who’ll all but have her as an equal.

Peggy is a popular favorite character because she’s got the most accessible heart. Even when she’s being cruel, cranky, selfish, vain, and insensitive, she’s acting in the name of the wholly human desire to be something great. You are, Peggy.

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“And people say New York’s not friendly!”

The beauty of Peter Dyckman Campbell has always been his transparency, a quality he’s fought long and hard to overcome, even (especially) when the party from whom he’s trying to obfuscate the truth is himself.

Anchored by a wicked misconception of entitlement, Pete is far more a victim than he is a villain. But because he’s almost a villain, it’s usually kind of satisfying to see him on the losing end. (Especially when the “losing end” involves a chaotically misguided reconciliation with the wife who hates him and a relocation to a city where he’ll never belong. Enjoy Wichita, Pete.)

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“I know people say life goes on, and it does but no one tells you that’s not a good thing.”

It hasn’t always been easy to sympathize with Betty, whose emotional immaturity has kept her from maintaining a positive relationship with any of her children. Seeing herself as a perpetual victim, it is, in fact, in the wake of Betty’s biggest tragedy yet that she finally allows herself to be a “winner.”

From Season 1 on, Betty has sought happiness in a number of realms — therapy, horseback riding, a second marriage — though has submitted all along the timeline to coming up short of her aspirations. Facing the formidable adversary of terminal cancer, Betty decides finally to put up a fight. She’s going to continue to try to be happy, and to allow her daughter that same privilege. I think we all underestimated just how much we could root for the former Ms. Hofstadt.

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“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.”

As his secretary Shirley puts it, Mr. Sterling has always been very amusing. So charming, in fact, that we’ve managed to put up with him as a constant craven disappointment. He left his wife for the thrills of a fling with a younger woman, maintained ambivalence toward his child with Joan, and let Sterling Cooper slip through his fingers… twice.

Roger is a man with no understanding of consequence and no time between drinks and wisecracks for a moment of forethought. But his invincibility has shown its expiration date, leaving Roger without a kingdom, nor an identity. But he does have that mustache.

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

The tragedy of Joan is unparalleled on Mad Men. Stronger, smarter, and more competent than most anyone in her eyeline, yet too beheld by a world on its way out to make it in the new one… which isn’t quite ready for her anyhow.

As far as her own happiness is concerned, all Joan can ever do is settle. But, considered in tandem with Peggy, to whom Joan once said, “I do take some credit for your success,” we understand people like Joan to pave the way for those like Peggy. She might never reap the benefits thereof personally, but Joan represents better than any other character the graduation of “the old world” into the “new.”

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“After an hour and a half of not smoking, Neville Chamberlain would have given Hitler his mother as a dance partner.”

The all-knowing mysophobe who adores Ayn Rand and Japanese culture, Bertram Cooper is as warmly mysterious in death as he was surveilling the halls of his advertising empire. Bert always considered himself a kindred spirit with Don, a fact that carries a good of weight when we consider the circumstances of the character’s death: watching Buzz Aldrin and Neil Armstrong set foot on the moon, and recognizing that “his time” is over. Not with mourning, but with awe. If Don can reach that recognition, he might earn the happiest ending to which he’s entitled.

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“When I think about forever, I get upset.”

We’d never expect her mother, Betty, to be the prophesier of Sally’s prosperous life yet to come, but Mad Men has always surprised us. Sally, riddled with intellect, pluck, heart, and integrity, is going to be fine. Not anchored down by her traumas as were her parents, nor free of character-building challenges like Pete or Roger, Sally has everything going for her. We’ll never see her become an adult, but it’s sure been an unexpected thrill watching her grow up.

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“We were having a conversation.”

There were too many Bobbys. Fewer Bobbys next time.

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“I wish we really had a second floor so I could jump off it.”

In a company, and a decade, filled with thick-headed and narrow-minded dolts, Harry Crane stands tall. Chauvinism, bigotry, homophobia, dishonesty, and unrelenting greed. He’s a class act.

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In lieu of a quotation or character analysis, here’s a GIF of him tapdancing.

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“Zous bissou bissou.”

Don sure does have a thing for the emotionally undeveloped, doesn’t he? Sure, Megan is a good deal more benevolent than most of the folks on Mad Men, but you can chalk that up to the fact that she essentially lives in a fantasy world. And no, she’s not Sharon freakin’ Tate.

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“I wish you were waiting for me.”

Henry is boring.

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“I will destroy you.”

Just as vapid and affected as her slime-ball of a husband Pete, Trudy at least knows how to work those Disney eyes for audience sympathy.

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“You were expecting me to be a man. My father was, too.”

Of all of Don’s extramarital affairs, Rachel is the only one who has (so far) visited him from beyond the grave. Then again, Don has also been visited by Bert Cooper and his estranged brother, so it’s hard to say what any of it really means.

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“Do you like Ukrainian food?”

The lord and savior of all pseudo-intellectual hipster douchebags, Paul Kinsey is a hoot and a half to watch dig himself into utter humiliation every time he speaks. His descent into a Star Trek episode-writing Hari Krishna was Shakespearean-level character marauding.

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“So we’re supposed to believe that people are living one way and secretly thinking the exact opposite? That’s ridiculous.”

You want to know what ever happened to Salvatore Romano? Here’s a good idea of how it might have gone down, straight from the horse’s mouth.

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Freddie Rumsen

“Are you just going to kill yourself? Give them what they want? Or go in your bedroom, get in uniform, fix your bayonet, and hit the parade? Do the work, Don.”

Equal parts schlemiel and schlimazel, Freddie Rumsen has been known to pull it all together to draw himself, and those he cares about — namely, Peggy and Don — out of a funk. He’s far more than just the fellow who drenched his trousers before a big pitch.

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“Mr. Draper, I try to cover for you all the time.”

She drove a damn lawnmower over her new boss’ foot in the middle of the office. Lois is a freakin’ hero.

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[Drunkenly:] “Awww!”

You never quite knew what Jane’s real intentions were, in the office or in her relationship with Roger. After all, she does pride herself on being a very “discrete person.”

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“I thought you married Jane because I had gotten old. And then I realized it was because you had.”

Roger’s far more interesting and intelligent first wife, who more often than not has everyone in a five mile radius pegged for all their B.S.

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“He has no people!”

The deceased father of Betty Hofstadt who hated his son-in-law Don and may or may not live on in the soul of Betty’s plausibly illegitimate third child who bears his name. You know, that old story.

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“The bigger we are, the cheaper we can get it.”

Word of advice: If your “Uncle Herman” calls, have your secretary tell him you’re not in.

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Kurt and Smitty

“We don’t want people to mix us up.”

One loves Bob Dylan and wears the hell out of a turtleneck. The other is young.

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“Every job has its ups and downs.”

Get it? Because he’s an elevator operator! (Pete didn’t get it.)

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“I’ve been here ten months and no one’s ever asked me where I went to school.”

If there’s one thing we’ve learned from Lane Pryce, it’s to always assume that doom is coming whenever we see the Mets logo. But then again, we already knew that.

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“You work your ass off for months, bite your nails, for what? Heinz Baked Beans.”

Serving less a character in his own right and more as a beacon of safety and compassion for the oft alone Peggy, Stan is still someone we’re very happy to have aboard the Sterling Cooper team. And that beard, well… you’ve seen the beard.

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“I’ll tell you what takes guts: never having money for lunch.”

With feathers forever ruffled, Ginsberg stands in stark contrast to his smooth and debonair adman colleagues. Long before even a supercomputer drove him past the brink of sanity and self-harm, Ginsberg didn’t seem quite comfortable in his own skin. His tirades made for some of the best comic moments on Mad Men, and his mustache among the most ill-fitting.

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“It sounds like New Years Eve when they’re emptying the garbage, there’s so many bottles.”

The only of Don’s secretaries that didn’t seem halfway brain-dead or altogether nuts (and if you’re going to pick out Peggy, remember, she was a little of an oddball back in her desk days).

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“Advertising is not a very comfortable place for everyone.”

Shirley, may the world outside of Sterling Cooper offer greener pastures… and fewer coworkers mixing up your name.

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“We’re old and we’re married. They don’t want us.”

Perpetually frazzled.

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“We’re flawed because we want so much more. We’re ruined because we get these things and wish for what we had.”

As far as admen go, Ted’s a pretty good egg. Don’t get me wrong, he’s dopey and adulterous… but he’s just about as good as any of these shmoes come.

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Jim Cutler

“I want to make it clear: Unless this works, I’m against it.”

Nobody plays smug like Hamlin.

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“You don’t have any character. You’re just handsome! Stop kidding yourself!”

So Frasier Crane’s son turned out to be kind of a hothead.

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“I don’t remember everything that everybody says.”

Who’d have thunk that Don Draper’s absolute worst secretary (and remember, one of ‘em ran over some guy’s foot with a lawnmower… in the office) would become his spiritual caretaker in the new world of McCann? Granted, she has no idea where he is right now, but she’s doing a bang up job covering for him.

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“My wife’s a card.”

Lou Avery seems to have been roped into Mad Men for the same purpose that Vince Gilligan introduced a gang of neo-Nazis at the end of Breaking Bad: to remind us that while our main characters might be terrible, at least they’re not this terrible.

Though folksy and a lover of cartoons, Lou is nobody’s pal. He’s just about the most despicable character to earn an office at Sterling Cooper. We can only hope that his new life in Japan is riddled with personal and professional shortcomings.

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Anna Draper

“The only thing keeping you from being happy is the belief that you are alone.”

The angelic Anna Draper represents the only source of unconditional love that Don, or Dick, has ever in his life known… or at least been able to accept. The brightest spot in his dark history, Anna will always hold a unique place in our hero’s heart. Unfortunately, the shameful connotations with how they met never allowed Don to wholly enjoy his special relationship with his namesake’s widow. He’ll always be looking for another taste of that kind of love. Who knows if he’ll find it?

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Bob Benson

Bob Benson himself might never have uttered anything particularly memorable, but the “new Don Draper” (as he’s been deemed) was the provocateur of the most quoted line in Mad Men history. You know the one.

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“Can I have some of your hair?”

Ooh, Glen. Wonderfully creepy, dead-eyed Glen. Be careful in ‘Nam, buddy.

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Ida Blankenship

“It’s a business of sadists and masochists and you know which one you are.”

She was an astronaut.

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