‘Mad Men’: 50 Best Characters – Rolling Stone
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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

AMC

50

Guy MacKendrick

Showcase Episode: "Guy Walks Into an Advertising Agency"
Meet the new boss: Sterling Cooper gets a visit from Guy, the posh Brit who's running the shop from now on. He walks around shaking hands — polished, confident, every inch a gentleman. Except his first day at the office goes very, very badly, thanks to a runaway lawn mower. Poor Guy — introduced with so much fanfare, mopped up so fast. A perfect example of how Mad Men loves to set you up and then torpedo your expectations. As Joan says, "That's life. One day you're on top of the world, the next minute some secretary is running you over with a lawn mower."

Mad Men

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

Justina Mintz/AMC

49

Trudy Campbell

Showcase Episode: "New Amsterdam"
Being married to Pete Campbell — now there's a fate you wouldn't wish on anyone. Yet Alison Brie's Trudy is quite the little schemer behind the scenes. Her all-time best moment comes while she's lurking in the next room: "Peter, may I speak to you for a moment?" Eventually she wises up and leaves — but since they're the only two people who could ever put up with each other, maybe they should admit defeat and reunite. Only Trudy would get hot and bothered when Pete punches out the prep-school admissions director: another battle in the MacDonald-vs.-Campbell clan war.

Mad Men

Rich Sommer as Harry Crane - Mad Men _ Season 7, Episode 4 - Photo Credit: Justina Mintz/AMC

Justina Mintz/AMC

48

Harry Crane

Showcase Episode: "The Wheel"
A creepier, sweatier Pete Campbell, with no redeeming qualities, except maybe his touching fondness for White Castle burgers. Some of us have never forgiven him for ratting out Sal and getting him fired. Harry Crane was a likeable loser in the early seasons, always inept at sucking up to big shots — as in his painful attempt to discuss modern art with Bert Cooper. He finally gets some respect when he meets his soul mate Jim Cutler, who tells him, "You have stiff competition, but I believe you to be the most dishonest man I have ever worked with." At Sterling Cooper, that's high praise.

Mad Men

AMC

47

Bethany Van Nuys

Showcase Episode: "The Summer Man"
One of the many glittery ladies who flicker in and out of Don Draper's life, Bethany is an aspiring actress who works as a stand-in at the Metropolitan Opera. When she describes her stage routine to Don, she's basically describing his life as well: "I'm a wench, I'm a courtesan, part of a harem. It depends on the opera." She performs a prima donna solo recital on Don in the back of a taxi, marking her man ("What are you doing?" "Making you comfortable") and departing into the night with the words: "To be continued." Way to make an exit, Bethany.

Danny Siegel

Stan Rizzo (Jay R. Ferguson) and Danny Siegel (Danny Strong) - Mad Men - Season 4, Episode 11 - Photo Credit: Michael Yarish/AMC

AMC

46

Danny Siegel

Showcase Episode: "Waldorf Stories"
Roger Sterling's second wife's idiot nephew, Danny stumbled into a gig at Sterling Cooper after he pitched a dumb idea that Don ended up accidentally using. Danny was always a cure for the common Mad Men episode, the butt of everyone's cruelest jokes — even Peggy came to enjoy having him and his pipe around. He was last seen making the Hollywood party scene. Played by Danny Strong, who went on to win an Emmy for writing Game Change and then co-created Empire, because the universe is one crazy place.

Mad Men

Carin Baer/AMC

45

Horace “Ho Ho” Cook

Showcase Episode: "The Arrangements"
Pete's college chum from Dartmouth has money — lots of money — and a dream: He wants to make jai alai as popular as baseball. "Ho Ho" wants to spend a fortune pushing this sport, even when Don tries to warn him off, and plans to make a matinee idol out of the the sport's star, Paxti. (This latter idea is responsible for the Clueless-worthy line, "I'm terrified of him catching balls in the face.") Sterling Cooper gets a case of "bill it to the kid" fever, since jai alai will never become the national pastime, but conning suckers is. Cook's hard-ass dad is a real piece of work, too. "My father hates Kennedy, because he knew Old Joe when they were criminals together."

Mad Men

Harry Hamlin as Jim Cutler and Sola Bamis as Shirley - Mad Men _ Season 7, Episode 3 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

44

Jim Cutler

Showcase Episode: "Waterloo"
Okay, so that Cutler, Gleeson & Chaough merger didn't quite work out. But it did bring a splendid new villain into Don's life: Harry Hamlin's Jim Cutler, who looks down on everyone through his giant Barry Goldwater glasses. He tries to squeeze Don out, with a lot of help from Don's liquor cabinet, in favor of budding cartoonist Lou Avery. His motto: "Unless this works, I'm against it."

Mad Men
43

The Madam

Showcase Episode: "Signal 30"
Mad Men has to hold some kind of record for one-scene sensations — characters who only need a moment or two onscreen to burn themselves onto your brain forever. Think of Roger Sterling's divorce lawyer ("I have a list of conditions and an alimony that could support Rita Hayworth"), the Belle Jolie lipstick salesman, Pete Campbell's dad, the Clio Awards MC ("Gentlemen, let's pace ourselves"), Achilles the janitor or Duck Phillips' dog. But few characters make a bigger impression in less time than the whorehouse madam (veteran character actress Eve Gordon) who notices Don Draper alone at the bar. They recognize each other as kindred spirits, or at least people who know way too much about whorehouses. "So expert, what do you think? Should I get a TV in here?" A moment of bonding — and then back to business.

(Note: In case you're keeping score of Mad Men's endless JFK obsessions, Eve Gordon played Marilyn Monroe in the 1991 miniseries about Jackie Kennedy. Happy birthday, Mr. President!)

Mad Men

Carin Baer/AMC

42

Jeffrey Graves

Another great one-shot. Paul Kinsey's Princeton pal Jeffrey shows up at the Sterling Cooper office to get the crew high, including newbie Peggy Olson. ("My name is Peggy Olson and I want to smoke some marijuana.") They all spend a strange stoned afternoon together, though it gets ugly when Jeffrey taunts Paul about his Jersey roots and his expulsion from the Princeton Tigertones. (Paul is touchy about his vocal skills.) But they reconcile for a bizarrely touching duet on "Hello! Ma Baby," which gets the ultimate rave review from Peggy: "I am so high!"

Mad Men

Sola Bamis as Shirley and Teyonah Parris as Dawn Chambers - Mad Men _ Season 7, Episode 2 - Photo Credit: Courtesy of AMC

AMC

41

Shirley

Showcase Episode: "A Day's Work"
Loads of women at the Sterling Cooper office excel at making so-over-this-bullshit faces, but few can match Shirley. Especially when she gets her bouquet of roses stolen by Peggy: "I'm getting her coffee and I'm taking my time." She gives notice to Roger with a hilariously sincere attempt at a compliment: "You're very amusing." That one stings, and make no mistake, it was meant to.

Mad Men

Katherine Olson (Myra Turley) - Mad Men - Season 5, Episode 7 - Photo Credit: Ron Jaffe/AMC

Ron Jaffe/AMC

40

Katherine Olson

Showcase Episode: "The Suitcase"
Peggy's mom is a tough old Catholic lady from Bay Ridge, where she probably goes to church with the young Tony Manero. She adores her daughter, calling her "Peaches," but she's usually yelling at her, which might be why we haven't seen her around the Peggysphere in a few years.

Mad Men

Peyton List as Jane Siegel and John Slattery as Roger Sterling - Mad Men - Season 2, Episode 11 - Photo Credit: Carin Baer/AMC

Carin Baer/AMC

39

Jane Siegel Sterling

Showcase Episode: "Far Away Places"
Roger marrying a 20-year-old secretary — how did that go wrong? At first Jane sets her sights on Don, but she settles for Roger, who admittedly brings his A-game. ("Where did you get that sweater? I want to make sure my daughter never buys it.") Jane is a self-styled poet and clairvoyant who offers a poignant epitaph for JFK: "He was so handsome and now I'll never get to vote for him!" She also brings Roger along for her fateful acid trip, which doesn't go as planned.

Mad Men

Kiernan Shipka as Sally Draper and Ryan Cutrona as Gene Hofstadt - Mad Men - Season 3- Photo Credit: Carin Baer/AMC

Carin Baer/AMC

38

Grandpa Gene

Showcase Episode: "The Arrangements"
The father-in-law from hell, and Don Draper deserves no less. Betty's dad is a WWI vet who used to fine his kids for small talk. He puts salt on his ice cream, shows off his war medals to his grandson ("I should have another one for beating the clap") and constantly baits Don. The only person on earth he respects? Sally, the girl everybody else ignores. Grandpa Gene gives her driving lessons and makes her read The Decline and Fall of the Roman Empire out loud every night. He's the first adult to tell Sally she's smart. Let's hope she remembers him fondly, since nobody else will.

Mad Men

Pauline Francis (Pamela Dunlap) - Mad Men - Season 5, Episode 3 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

37

Pauline Francis

Showcase Episode: "Mystery Date"
And on the other end of the grandparent spectrum, there's Henry Francis' nightmare of a mom. Pauline's most likeable moment comes when she teaches Sally to pop a Seconal ("Do you know how to take a pill?") and tells gruesome crime stories until she hides under the couch with a butcher knife. Sweet dreams, Sally.

Mad Men

Joyce Ramsey (Zosia Mamet) and Peggy Olson (Elisabeth Moss) - Mad Men - Season 4, Episode 4 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

36

Joyce Ramsey

Showcase Episode: "The Rejected"
Peggy's hipster lesbian pal Joyce (a photo editor at Life) was the first chance we all got to see Zosia Mamet in action. Joyce has to get docked a couple notches for introducing Peggy to Abe, a boyfriend so insufferable that fans cheered when Peggy harpooned him. (Peggy's always had dodgy taste in men, but she really hit rock bottom with Abe.) It was always sweet how Joyce called her "Pegasus," too. Mamet ended up stealing Girls as Shoshanna, a New York girl who's basically the 180-degree opposite of this one.

Mad Men

Bert Cooper (Robert Morse) and Lee Garner Sr. (John Cullum) - Mad Men - Season 1, Episode 11 - Photo Credit: Carin Baer/AMC

Carin Baer/AMC

35

Lee Garner Sr.

Showcase Episode: "Indian Summer"
The Lucky Strike patriarch is even creepier than his son, which is saying something. He takes pride in his tobacco ("It's toasted!") and takes offense when the meddling Yankees in the Federal Trade Council suggest there could be something poisonous about it — might as well live in Russia. He fumes about the money he wastes on lawyers: "I've seen a girl fight harder on a first date than these Beltway shuttlecocks!"

Mad Men

AMC

34

Joy

Showcase Episode: "The Jet Set"
One of the funniest examples of Mad Men's often ham-fisted attempts at symbolism: "Hello. I'm Joy." This Eurotrash princess meets Don in Palm Springs and lures him into a decadent world of globe-trotting idle aristocrats, with her father the Viscount presiding over his court. It's safe to say she's the only woman who's ever read Faulkner while in bed with Don. Joy poses a question that haunts him long after he leaves Palm Springs: "Why would you deny yourself something you want?"

Mad Men

AMC

33

St. John Powell

Showcase Episode: "Meditations in an Emergency"
Pronounced "Sinjun," which is British for "slimeball," the delightfully evil overlord takes over Sterling Cooper from the Americans and peddles the firm to the hated McCann Erickson, selling out his loyal hatchet man Lane Pryce in the bargain. (Giving him a dead snake in a gift-wrapped box — classy touch, St. John.)  Played by Charles Shaughnessy, eternally beloved as Miss-tah Sheff-eee-yeld from The Nanny, although not even the sound of Fran Drescher's voice grates on his nerves like the sound of Lane wishing him a happy Christmas.

Mad Men

Don Draper (Jon Hamm), Megan Calvet (Jessica Pare) and Roger Sterling (John Slattery) - Mad Men - Season 4, Episode 13 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

32

Megan Calvet Draper

Showcase Episode: "Tomorrowland"
Strange as it seems now, for a dozen episodes or so, Milkshake Megan was the show's smartest and most intriguing character. Even though Don barely knows this girl, he marries her because she's the first human he's ever met who knows how to wipe up a spilled milkshake without tears. Like a lot of decisions people make on Mad Men, it seemed like a good idea at the time. But then Megan quit the firm to be an actress and instantly turned into a whimpering annoyance, despite her still-admirable taste in miniskirts. (Respect to the outfit she wore the night the Draper residence got burglarized, while she was "off on the casting couch," as Betty tactfully put it.) She makes the list based on her early achievements in zou-bisou-ology.

Mad Men

Carin Baer/AMC

31

Duck Phillips

Showcase Episode: "Three Sundays"
So many ups and downs for the Duck — most of them involving the bottle, as in the drunken rant that gets him dragged out by security at the Clio Awards. (Roger Sterling cracks, "I miss working with that guy.") His pivotal moment: at a secret meeting with the Brits, taking a sad look into his martini glass, right before he takes that fateful sip and makes his pitch to sell Sterling Cooper. Alas, he never could hold his liquor.

Mad Men

Midge Daniels (Rosemarie DeWitt) - Mad Men - Season 4, Episode 12 - Photo Credit: Michael Yarish/AMC

Michael Yarish/AMC

30

Midge Daniels

Showcase Episode: "The Hobo Code"
Don's beatnik girlfriend from the Village, a footloose painter with a crew of boho pals who like to get high and listen to Miles. The most free-spirited of Don's paramours, the kind of "I don't make plans and I don't make breakfast" gal who livens up a date by throwing a TV out the window.

Mad Men

AMC

29

Kurt Smith

Showcase Episode: "The Jet Set"
When the Sterling Cooper bosses decide to dip a toe in the Sixties youth movement, they hire the duo or Kurt and Smitty, who look like the world's first Simon & Garfunkel cover band. Smitty reads Don the original Port Huron Statement (not the compromised second draft), while German designer Kurt casually comes out as the first openly gay dude anyone's ever met. ("I make love with the men, not the women.") Oh, the sad look on Sal's face. In a sublimely moving scene, Kurt meets Peggy for a Bob Dylan concert, then blows off the show to stay home ("You are drinking sad") and change her life with her first mod haircut.

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.