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50 Best ‘Mad Men’ Characters

From one-off cameos to Sterling-Cooper’s core players, we’re ranking the show’s most memorable characters

Sex. Booze. Money. Corruption. Mad Men has given us a host of brilliantly depraved rogues over the past eight seasons. (Or seven, if you’re into AMC’s droll accounting.) So many great characters, with so few moral standards. As Matthew Weiner’s saga of the Sixties ad game heads for the final curtain, it’s time to count down the 50 best characters. Some keep evolving over the years, going through drastic changes. Others just blaze for an episode or two. Really, it’s about quality not quantity — sorry, but no matter how much screen time Lou Avery gobbles up, he can’t hang with a glorious one-shot like Ho-Ho. Some of these characters are fast with a quip, some out for a buck, others just here for a drink. But they’re all unforgettable.

Mad Men

Mona Sterling (Talia Balsam) - Mad Men_Season 6, Episode 2_"The Doorway" - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

27

Mona Sterling

Showcase Episode: "The Grown-Ups"
Roger's first wife is a lioness, as he says, and it's no surprise she rebounds from the marriage better than he does. Talia Balsam is married to John Slattery in real life, which might help explain their surefire chemistry. Balsam adds a lot to the Six Degrees of Mad Men game, because she was on an early episode of Dallas (she's the pregnant teen who tries to sell her baby to Sue Ellen) — making her the crucial historical link between Dallas and Mad Men.

Mad Men

Jay R. Ferguson as Stan Rizzo - Mad Men _ Season 7, Episode 7 - Photo Credit: Justina Mintz/AMC

Justina Mintz/AMC

26

Stan Rizzo

Showcase Episode: "Time & Life"
After starting out as just another macho office clod, Stan developed warmth and soul in proportion to his beard — definitely Mad Men's most successful experiment in facial hair. Jay R. Ferguson is masterful in the scene where Peggy tells him about giving her baby up for adoption — as he realizes where she's going, he listens with empathy and respect. It's the show's most optimistic sign that sexism isn't necessarily a life sentence. Love the groovy Moshe Dayan poster over his bed, too.

Mad Men

AMC

25

The Hobo

Showcase Episode: "The Hobo Code"
Played by Paul Schulze — Carmela's Father Phil on The Sopranos — this drifter makes the young Dick Whitman "an honorary," and teaches him the hobo code. In short: move fast, go it alone, con the rubes, read their faces, leave your mark on them so other hobos know the deal, then get back out on the road. Even now, Don Draper can't resist the urge to hit the open road and ride the rails.

Mad Men

Michael Yarish/AMC

24

Michael Ginsberg

Showcase Episode: "Far Away Places"
Ginsberg definitely rates on the Roger Sterling spectrum of Jewishness: "Fiddler on the Roof — audience or cast?" This twitchy kid claims to be a full-blooded Martian, even though his dad says he was born in a concentration camp. Ginsberg eventually grows a mustache, which on Mad Men is always a sign of imminent mental collapse.

Mad Men

AMC

23

Alice Cooper

Showcase Episode: "The Mountain King"
It makes sense that Bert Cooper's bad-ass sister shares her name with a rock & roll god — "No More Mister Nice Guy" could be her theme song. Alice Cooper is the only one who gets away with wearing shoes in Bert's office ("My stockings cost more than your carpet") or calling him Bertram. She also used to be Roger Sterling's babysitter, which might be why she gives him so much shade about marrying a 20-year-old. ("You have your children to think of." Meee-yow!) She talks her brother into selling off his life's work — but as the other Alice Cooper would put it, if that don't suit you, that's a drag.

Mad Men

Marie Calvet (Julia Ormond) - Mad Men - Season 5, Episode 7 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

22

Marie Calvet

Showcase Episode: "At the Codfish Ball"
Ooh la la: Julia Ormond as Don's formidable ex-mother-in-law. Roger can't resist her accented "I have desperate need of youuuuu" any more than we can. Marie stayed a worthwhile character much longer than her daughter did.

Mad Men

Carin Baer/AMC

21

Suzanne Farrell

Showcase Episode: "The Gypsy and the Hobo"
Don has a torrid affair with Sally's schoolteacher, because of course he does. Unlike most of the lost strays he links up with, Suzanne can keep up with him crazy-wise, because she's as profoundly fucked up as he is — a long-distance runner who waits all night outside Don's house, in his car, until she realizes he's not coming back for her.

Mad Men

AMC

20

Woman on the Train

Showcase Episode: "Nixon vs. Kennedy"
She's only in one scene — but what a scene. It's the moment that truly turns Dick Whitman into Don Draper; just back from Korea, in his new identity, he meets a woman on a train, probably the first person who ever spoke a kind word to him. She might be a war widow herself (she's wearing black gloves) but she gives a heartbreaking little speech to Don ("You've got your whole life ahead of you — forget that boy in the box") and flirtatiously suggests, "Let me buy a soldier a drink?" All these years later, Don Draper is still that scared soldier, looking for that woman.

Mad Men

AMC

19

Henry Francis

Showcase Episode: "The Grown-Ups"
Betty's second husband is a real upgrade — a gallant Rockefeller Republican who's so rational and well-adjusted, he seems to have wandered in from some other show entirely. When Betty rages about hating Don, he's there with a sane reply: "Hate's a strong word, Betty. I hate Nazis." The worst you can say about the guy is he's kinda bitchy about the fact that his wife used to sleep with Don Draper, but honestly, can you blame him?

Mad Men

AMC

18

Paul Kinsey

Showcase Episode: "Nixon vs. Kennedy"
The office hepcat: a young Orson Welles type smoking his pipe, growing his beard, writing plays and throwing parties where he busts out astoundingly obscure R&B sides. (George McGregor and the Bronzettes' "Temptation Is Hard To Fight" — damn! Easily the best song I discovered via Mad Men. Thanks, DJ Death Is My Client!) Paul has an intriguing romantic history with Joan. But he tragically gets left out of the new-model Sterling Cooper and things go downhill for him, until he winds up a Hare Krishna. Hey, it's better than what happened to the real Orson Welles.

Mad Men

Anna Draper (Melinda Page Hamilton) - Mad Men - Season 4, Episode 3 - Photo Credit: Adam Taylor/AMC

Adam Taylor/AMC

17

Anna Draper

Showcase Episode: "The Good News"
When the original Don Draper got blown up in Korea, leaving the young Dick Whitman to steal his dogtags and identity, he left a wife behind. After she catches up with Dick, they begin one of Mad Men's most touching and endearing friendships…especially when he paints her living room in his boxer shorts. True, their whole relationship is founded on another one of his lies. (He says her husband got killed in action, leaving out the detail that Dick Whitman was the one who blew him up.) But Anna knows the man and his secrets better than anyone.

Mad Men

Ken Cosgrove (Aaron Staton) - Mad Men_Season 6, Episode 4_"To Have and To Hold" - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

16

Ken Cosgrove

Showcase Episode: "Signal 30"
Ken's really a few different characters — he begins as a sexist jerk who mocks Peggy behind her back, but he turns into a surprising stand-up guy (as well as a loyal friend to the secretary-turned-ace-copywriter). He's also a science-fiction author who publishes his stories under secret pen names. Along the way, he manages to lose an eye in a hunting accident (was Dick Cheney working for Buick?) and marry the girl from The Secret World of Alex Mack. Seems like an even trade.

Mad Men

Faye Miller (Cara Buono) - Mad Men - Season 4, Episode 4 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

15

Dr. Faye Miller

Showcase Episode: "The Beautiful Girls"
Yet another inspired Sopranos casting touch — Carla Buono was Christopher's wife Kelli before playing Dr. Faye Miller, the steamy psychiatrist who analyzes the fuck out of Don. She totally has his number: "You only like the beginnings of things." And oh yeah, she has a dad in the mob — "He's a handsome two-bit gangster like you."

Mad Men

Vincent Kartheiser as Pete Campbell - Mad Men _ Season 7, Episode 6 - Photo Credit; Justina Mintz/AMC

Justina Mintz/AMC

14

Pete Campbell

Showcase Episode: "New Amsterdam"
From the start, one of the lowest critters in the Mad Men universe — but as soon as we meet his horrible old-money WASP family, we understand. Nobody ever taught Pete how to be a human being, and he learns by random baby steps, although too late to save his marriage. He remains an unimpeachable yeller of punchlines, from "Marriage is a racket" to "Not great, Bob!"

Mad Men

Betty Draper (January Jones) - Mad Men - Season 4, Episode 13 - Photo Credit: Jordin Althaus/AMC

Jordin Althaus/AMC

13

Betty Draper Francis

Showcase Episode: "Meditations in an Emergency"
Don's first wife lives out the curse of the feminine mystique, a fashion model who marries a dashing young Don Draper only to keep finding out how alone she is. Her outfits are Mad Men fashion at its best — especially the dress she wears to meet Henry Francis at Swenson's Bakery. She goes back to school to get her psych degree; it's weird to see her sit at the kitchen table reading Freud's Dora: A Case Study of Hysteria, a book that once seemed like her life story. Here's a whipped-cream toast to you, Bertie — straight from the can.

Mad Men

AMC

12

Conrad Hilton

Showcase Episode: "Seven Twenty Three"
Based on the real-life hotel tycoon — Paris' great-grandpa — Connie Hilton meets Don on Derby Day, where they're both hiding from their hosts in an otherwise empty bar. This New Mexico cowpoke tyrant is the crustiest, funniest and just-plain-insanest of clients. He orders Don around, calls him at all hours, complains he doesn't have a Bible on his desk and takes no guff: "By golly, you're prickly!" Probably the only Mad Men character name-checked in a Pavement song ("Fin"), although "AT&T" could have been written about Don.

Mad Men

AMC

11

Freddy Rumsen

Showcase Episode: "Six Months Leave"
Nobody better exemplifies how Mad Men goes for the long bomb, character-wise. Freddy Rumsen starts out a drunken mess with a weak bladder but a heart of gold — if he hadn't overheard Peggy's "basket of kisses" comment and groomed her as a copywriter, she'd still be stuck in the secretarial pool. Over the years, he evolves into a different guy: sober, thoughtful, doling out Yoda-like wisdom. ("Do the work, Don!") Played by Joel Murray (Bill's brother), Freddy is a lovable slob every step of the way.

Mad Men

AMC

10

Sal Romano

Showcase Episode: "The Hobo Code"
Sal probably tops the list of long-gone regulars fans are praying to see again in the finale. Lord, this man knew how to give a bitchy shrug. The debonair yet tragically closeted art director always had to hide his private heartache, but he impressed Joan with his cologne and Lois with his "ciao ciao." I hope Sal made it to the Seventies in one piece — he deserved it.

Mad Men

Ida Blankenship (Randee Heller) - Mad Men - Season 4, Episode 5 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

9

Miss Ida Blankenship

Showcase Episode: "The Beautiful Girls"
Don's coolest secretary, hands down. You could count on Miss Blankenship to greet Don with a line like "your daughter's psychiatrist called" or "you got a call while you were in the toilet." She always found a way to be a pain in the ass for the whole office, right up to the end. (And for a few hours after that.) As Bert put it, "She was an astronaut." Desperate request to AMC and Matthew Weiner: Can we get a Better Call Saul-style prequel about Ida Blankenship, maybe about her younger days as the Queen of Perversions?

Mad Men

Craig Blankenhorn/AMC

8

Rachel Menken

Showcase Episode: "Babylon"
Don's coolest girlfriend, hands down. The Jewish department-store magnate understands Don well enough to see through his let's-run-away fantasies: "What are you, 15 years old?" But she never relinquishes her hold on him, even after she becomes Mrs. Tilden Katz. (Or after Maggie Siff becomes a star on Sons of Anarchy.)

Mad Men

AMC

7

Bert Cooper

Showcase Episode: "Seven Twenty Three"
The WASP Vito Corleone. Sterling Cooper's patriarch might seem genial and absent-minded, doddering around in his socks, lecturing the secretaries on the evils of chewing gum, socializing with his fellow power brokers. ("I just spent the night in a smoke-filled room at the Waldorf with every Republican luminary save MacArthur and Jesus.") But as soon as he wants something, he has no trouble dropping the mask to reveal the Scary Bert side. He knows everyone's secrets, but never reveals his own. (We never did find out whether "the late Mrs. Cooper" meant his wife or mother.) Played by Broadway veteran Robert Morse, he got an unforgettable farewell, dancing away to "The Best Things in Life Are Free."

Mad Men

Lane Pryce (Jared Harris) - Mad Men - Season 3 - Photo Credit: Carin Baer/AMC

Carin Baer/AMC

6

Lane Pryce

Showcase Episode: "The Good News"
The most poignant character — the British business brain who gets brought in to fire people, but ends up desperately yearning to be one of the Americans. ("I've been here 10 months and nobody's asked me where I went to school.") He bonds with Don over Japanese monster movies and hookers; he falls in love with a Playboy bunny; he repeatedly shatters the hearts of us poor deluded Joan/Lane 'shippers. He left a little chewing gum on the pubis of our hearts. Huzzah!

Mad Men

Jon Hamm as Don Draper and Kiernan Shipka as Sally Draper - Mad Men _ Season 7, Episode 2 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

5

Sally Draper

Showcase Episode: "At The Codfish Ball"
Let's face it, 99 percent of child actors suck. So it makes zero sense that the show lucked out with a Sally (Kiernan Shipka) who grew up to be a real actor, one who could actually help carry the emotional heft of the story. (This literally never happens.) And Sally has turned out to be crucial — she's the only living soul Don wants to impress, yet she's the one he has the toughest time fooling. (As a great man once sang, "The ones who love us least are the ones we'll die to please.") Is it weird she never brings up the fact that he took her to see the Beatles at Shea Stadium? Wouldn't most people have trouble shutting up about that?

Mad Men

Doug Hyun/AMC

4

Joan Holloway Harris

Showcase Episode: "Christmas Waltz"
How in denial are we about the end of Mad Men? We keep watching the Everclear video Christina Hendricks starred in, back in her grunge-goth days. ("One Hit Wonder," it was called. Not a bad tune!) Right from the start, Joan had plenty of smoldering rage. In the episode where she played the accordion and sang "C'est Magnifique," it raised all these questions: Namely, what kind of pageant-princess hellhole did this woman emerge from? There's so much nobody knows about the suffering Joan has endured, including a bonus marriage she never mentioned until a few weeks ago. But Joan's got the sneer everybody else is scared of — especially Roger, who'll never get over her.

Peggy Olson

Elisabeth Moss as Peggy Olson - Mad Men _ Season 7B, Episode 12 - Photo Credit: Courtesy of AMC

AMC

3

Peggy Olson

Showcase Episode: "The Suitcase"
"I am one of those girls," Peggy told her big sister when she first decided to move to Manhattan. And look at her now: strutting down the hallway, with shades, cigarette and Thermos in place. Always easily overlooked by people around her, Peggy had a tough time getting taken seriously at first — especially by her usual underminer Joan, who never met a Peggy triumph she couldn't smother in side-eye. ("I'm glad your other work was suffering for a reason." Nice one.) But Peggy will always be the new girl, because she keeps moving forward (sometimes on roller skates), the way her once and future mentor Don taught her. And her weird bond with Don has sustained them both through all their Burger Chef ups and Pizza House downs.

Mad Men

John Slattery as Roger Sterling - Mad Men _ Season 7, Episode 3 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

2

Roger Sterling

Showcase Episode: "Shut The Door, Have A Seat"
Has anyone in TV history made a deadlier wisecrack delivery machine? Compared to Roger Sterling, Johnny Carson was some tongue-tied amateur. His toast at his daughter's wedding — the day after the JFK assassination — remains a model for how to bullshit your way through a disaster, as does his whole life. John Slattery brings the "Have a drink, it'll make me look younger" pain; under all his bravado, he's a salesman with nothing to sell. But Roger's the Proposition Joe of Mad Men: When he steps into a scene, you can see the others light up. Everybody's best scenes are their Roger scenes. So let's all raise a parting glass to this man. It'll make him look younger.

Mad Men

Jon Hamm as Don Draper - Mad Men _ Season 7B, Episode 10 - Photo Credit: Justina Mintz/AMC

Justina Mintz/AMC

1

Don Draper

Showcase Episode: "The Suitcase"
Who is Don Draper? You're face to face with the man who sold the world. The master seducer of the ad game. The sensitive piece of horseflesh. The mystery man who scams everyone around him into believing he knows their secrets. A liar and a thief. A trickster so persuasive, he regularly slips and starts believing his own promises, like a dealer who gets high on his own supply. The leading man who holds this sprawling story together. For some reason, people really want Don Draper to like them. Unfortunately for him, Don Draper is one of those people, which means he always keeps cracking up. But we can't take our eyes off him.

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