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The 70 Most Memorable Characters of ‘Mad Men,’ Ranked

The 70 Most Memorable Characters of 'Mad Men,' Ranked

This list was incredibly difficult to create, especially since the finale could change everything. We’ll update accordingly after Sunday, if necessary, but, at least for this moment, here is our ranking of the vast panorama of characters who appeared on “Mad Men” during its seven incredible seasons. What criteria was used? It’s hard to say for sure, but, “Who would we most want to share a drink with?” seems pretty solid. After all, it’s the “Mad Men” way.

READ MORE: Review: ‘Mad Men’ Season 7 Episode 13 ‘The Milk and Honey Route’ Finds Joy and Sorrow

70. Greg Harris

F— you, Greg. So many characters on “Mad Men” did so many terrible things, but the overwhelming majority of them found some opportunity for, if not redemption, then the opportunity to prove that they had some humanity within them. Greg was just the worst, from beginning to end. Poor Vietnam, to have Greg living within its borders. Greg makes this list only because it needs an absolute bottom (or top, depending how you look at it).

69. Duck Phillips

Oh, man. How to rank Duck? I mean, he wasn’t great to anyone in his life, but the way he’d periodically stagger about without any dignity technically makes me want to spare him some human sympathy… Wait. DUCK ABANDONED HIS DOG CHAUNCEY. QUESTION ANSWERED.

68. Archie Whitman

What a dick. Hey! Guess it’s a family name.

67. Abigail Whitman

It wasn’t Dick’s fault that his birth mother was a whore and his father was the worst, but she sure made him think it was. Things could have been worse for the foundling, in theory — Abigail Whitman did keep a roof over his head. But Christian charity didn’t cross over too much into the realm of human kindness.

66. Lou Avery

Ugh. Anyone who makes a creative feel bad for wanting to do great work can go straight to hell. (Or, I guess, Japan. Crash and burn in Japan, Lou.)

65. Midge Daniels

Aw, man. Midge. Don’s free-spirited girlfriend from Season 1 took a dark, dark turn in later years. She’s a sad memory, for sure. She exited with one of “Mad Men’s” most memorable quotes about substance abuse: “It’s drinking a hundred bottles of whiskey while someone licks your tits.” But while her descent into drugs is tragic, her rather blatant manipulation of Don (even prior to the heroin days) makes her relatively unsympathetic.

64. The Great Unnamed Masses of Women Don Has Slept With

Like the Hero with a Thousand Faces, but less to do with global trends in mythology and more to do with boobs. Never totally personality-less, but oftentimes indistinguishable.

63. Conrad Hilton

Free trip to Rome aside, what a cocktease this guy was, am I right? Whatever, Connie.

62. Margaret Sterling Hargrove

Sigh. Margaret. The hippie lifestyle might have treated some well. It might have truly meant something to a lot of people. But in Margaret’s case, it was an excuse to abandon her young son and less-young husband. It’s nice that Margaret found greater depth beyond debutante/wife. But LADY YOU HAVE A KID.

61. Joey Baird

Joey follows a pretty classic “Mad Men” character path: seemingly likable and fun at first, then exposed as a charmless fraud and shooed out of the narrative almost immediately. He offered up some pretty classic dick behavior in his final days, but even if it did end badly, we’ll always fondly remember his “‘John’… ‘Marsha’…” banter with Peggy.

60. Jane Siegel Sterling

Anything is possible on Finale Eve, but last we saw Jane, she’d pretty hardcore moved on from Roger, and it seems like they’re now on very different paths. While kind of a giant pill for much of her time on the show, Jane gave us the gift of LCD Roger, and for that we shall always be grateful.

59. Bobbie Barrett

Everything that happened between Peggy and Bobbie was great! Everything that happened between Don and Bobbie was not! Bobbie gets a pretty low placement as a result.

58. Diana Baur

Technically the reason Don set off on his end-of-series sojourn was to find Diana, though Don’s rarely needed a compelling reason to go on walkabout, and he was obsessed with her even before he knew about her tragic backstory. Was that obsession justified? Well, Elizabeth Reaser is a great actress. The character, like so many women Don was obsessed with, became a bit ephemeral. 

57. Danny Siegel

Say this for the guy who played Jonathan on “Buffy,” he knew exactly what he had going for him and knew exactly what he wanted. No wonder he was, ultimately, such a success in Hollywood.

56. Adam Whitman

I never really understood why Adam committed suicide, but then again, sometimes there’s never really an answer to that question. The fact that a reconnection with Don could have prevented it is… Well, of all the not-great things Don did over the course of the show, rejecting his half-brother wasn’t necessarily the worst. But Adam Whitman seemed like a decent person. One deserving of a family to miss him.

55. Arnold Rosen

What a doof. A nice doof. But, alas.

54. Mitchell Rosen

Also a doof. For different reasons from his father. But. Y’know.

53. Shirley

Shirley’s roses, and the battle over them, is one of television’s most awkwardly passive aggressive moments, and she deserves this ranking if only because of that. Shirley herself, beyond her interactions with Dawn, never truly had a chance to blossom. But that’s the show’s fault, not her own.

52. Jimmy Barrett

RANDOM TRIVIA ALERT: Patrick Fischler, an iconic Hey It’s That Guy, made a very memorable guest appearance in the “Millennium” episode “Jose Chung’s Doomsday Defense” as a representative of “Selfosophy.” He was also great as the fast-talking comedian whose big mouth caused no shortage of problems for Don, professionally and personally. He’s not a great human being, necessarily, but got the short end of the stick.

51. Helen Bishop

First she was the most scandalous addition to the neighborhood. Then she became a series regular on “Scandal”! Coincidence? Yes. It was a coincidence. But while relatively underdeveloped, the only single mother on Betty’s block added some interesting edge to the first season.

50. Gail Holloway

She might sass Joan occasionally, but you gotta admire the way Joan’s mom pitched in to basically co-raise her grandson. Total team player.

49. Sylvia Rosen

Don chose to seduce most ladies over the show’s seven seasons because, well, they were hot. Sylvia, tragically enough, seemed to engage Don’s interest mostly because of his self-destructive tendencies. And, like many women who fell into his sphere, she lacked real definition. She might honestly be more happy in her new relationship with an Avenger. (She certainly looks younger.)

48. Carol McCardy

Oh, man, Joan’s lesbian roommate from Season 1! God, poor Carol; sexing with Joan’s discards and never getting what she wanted. Poor Carol. This is a pity ranking. (She’s used to it, though.)

47. Rebecca Pryce

Lane Pryce’s wife didn’t get much time on screen — compared to other wives — but the way she bristled and rebelled against the paths thrust upon her made her someone to respect. Rebecca wasn’t happy, but unlike other women of her generation, she didn’t suffer in silence.

46. Katherine Olson

“You’re gonna get raped,” Peggy’s mother said upon learning that her daughter wanted to move to the city. “You’re lonely? Get a cat,” her mother said upon learning that her daughter wanted to move in with her boyfriend. Katherine Olson? Not a woman of modern sensibilities or massive compassion.

45. Émile Calvet

Oh, you Communist frog. You were a hoot.

44. Anita Olson Respola and Gerry Respola

Peggy’s sister and brother-in-law never made a huge impact, but the fact that Peggy was always relatively close with them (even during the rougher days, after Peggy’s adoption scandal and Anita’s struggle to handle it) helped her feel like a fully fleshed-out character. Also, the fact that Gerry helped (as much as he could) with Peggy’s maintenance needs indicates a certain level of compassion.

43. Lane Pryce

Loving Lane requires some application of selective memory. For instance, forgetting about the way he treated Joan and his wife from time to time, the way he’d skeeve out on Playboy bunnies or the girlfriends of random strangers. Personally, I’ll always love him best drunk as a skunk on the town with Don. “The ‘Umbrellas of Cherbourg’… Apparently, it’s for all the young lovers of the world.” Followed by:

42. Faye Miller

Remember when Dr. Faye told Don, “You’ll be married again in a year… I’m sorry. I always forget. Nobody wants to think they’re a type”? That was great. Faye was maybe one of Don’s best girlfriends. At the very least, she was certainly the smartest.

41. Megan Calver Draper

The lowest-ranked of the many Mrs. Drapers, largely because the balance between the amount of screen time and the amount of character development she received was always painfully out of balance. Megan always seemed less like a fully-formed person and more like a creature always seen through Don’s eyes. It’s not Jessica Pare’s performance that’s the issue, just what she’s given to work with. Megan proved to be brittle and insecure and best left to drift into the Hollywood acting scene. We leave you with a zou bisou, ma’am.

READ MORE: 7 Things to Learn from ‘Mad Men’ Creator Matthew Weiner About Compelling Storytelling (Exclusive Video)

40. Rachel Menken

Matthew Weiner’s seasons-long obsession with one of Don’s first, but most notable, mistresses has always been a bit baffling. (Though, as perhaps the show’s most prominently Jewish character, Weiner’s own statements this year about “Mad Men” as a show about the Jewish American experience perhaps helps make sense of it.) Point is, Maggie Siff has the sort of unusual beauty that always played well on this show, and Rachel was an honest and grounding influence on Don, one he very much needed when they first met. Her sad passing earlier this year may have kicked off a chain of events for Don we’re still not sure how to understand. Point is, she was an infrequent but influential force for good on the show.

39. Jim Cutler

Eh. You know what show Harry Hamlin was really great in? “Veronica Mars.” Just a crazy, creepy, charismatic, tour de force performance. Hamlin had been on “Mad Men” for at least three weeks before I realized he was the same actor; Jim Cutler has rarely been anything less than a bland stick-in-the-mud.

38. Glen Bishop

He might have been the creepiest kid in the neighborhood, but boyfriend grew up hot. And hey, what kid doesn’t have his creepy phase?

37. Joyce Ramsay

Ignoring the “Girls” haters, Zosia Mamet’s monotone delivery worked pretty well here. And Joyce pushed Peggy out of her comfort zone to some exciting new life experiences, like going to crazy parties, kissing girls and falling in love with Abe. Joyce is missed.

36. Francine Hanson

At the very least, it was always nice to see Anne Dudek — one of those great TV actors who has yet to land a perfect iconic role, instead bouncing from guest star appearance to guest star appearance. But Francine added a fun modern note when she and Betty met for coffee in Season 7a; Francine, in total, was great.

35. Gene Draper

This is where Gene belongs — the exact statistical middle of this list. This is the exact impact he has had on the show as a character. It’s not really his fault — he’s like seven years old as the series ends — but still.

34. Brooks Stanford Hargrove

Always kind of bland and flavorless, Brooks nonetheless proved himself to be a pretty decent guy in the aftermath of Margaret’s departure to a commune. I mean, he wasn’t capable of actually handling the problem. But he stuck around when other men might have fled. So, way to go Brooks. Way to go.

33. Paul Kinsey

Paul’s insane transformation from yet another lustful S&P employee to “Star Trek” spec script-writing Hare Krishna… Well, we didn’t see it coming.

32. Bobby Draper

Fun party game: pick your favorite Bobby Draper! I’m partial to No. 2, Seasons 1 and 2, as played by Aaron Hart. (But only after I looked up which one he was.)

31. Lois Sadler

Poor Lois. Or… maybe not? Imagine: The most awkward of Sterling Cooper’s secretaries, humiliated beyond belief by having run over a man’s foot with a lawnmower, goes to visit Guy MacKendrick in the hospital as he recovers from not just the loss of a foot, but the loss of his golf career. Her guilt makes her even more tender and sweet than usual. The crippled Guy, vulnerable and abandoned by his corporate overlords because of his injury, is desperate for even an ounce of genuine sympathy. Six months later, they’re married on the palatial grounds of his family’s country estate in Sussex. Decades later, their five children work together to run the successful landscaping business they co-founded (Lois’s humble roots make her uncomfortable with just accepting Guy’s family money). Every year, on their wedding anniversary, Lois buys Guy a new cane. He’s kept every one.

30. Harry Crane

Harry’s journey was basically the exact opposite of Ken’s — he went from being a vaguely decent human being to a total manwhore. He was consistently the most fabulously dressed man on the show, though, and that’s saying something.

29. Father Gill

It was pretty hot when Colin Hanks stripped down to a T-shirt to rock some acoustic guitar. Also, he was a nice person (especially for a Catholic priest). You cannot get it, Father Gill, but you are worthy of it.

28. Abe Drexler

The pantheon of Peggy Olson’s boyfriends isn’t terribly impressive. But Abe, at this point, remains the best. He was smart, sweet and understood Peggy pretty well. Sure, their relationship fell apart after she stabbed him, but honestly, that’s understandable.

27. Hollis

Poor Hollis, who not only shouldered the seasons-long burden of Only Black Man To Regularly Appear on Screen, but also the burden of Explaining Black People to Guys Like Pete Campbell. Hollis deserved a proper farewell, not what he got: Abandonment, following the Season 3 nuking of the original Sterling Cooper.

26. Marie Calvet

Megan’s mom and Roger Sterling as a steady item? Sure. It’s certainly not the weirdest thing to happen on this show. Marie’s kind of an unhappy person for most of the time we see her on the show, but it’s hard to imagine being unhappy with the modern and enlightened Roger of the show’s final days.

25. Cynthia Cosgrove

Larisa Oleynik played ALEX MACK! A+++ human. Also, Cynthia loves Ken Cosgrove’s writing. We, in turn, love Cynthia.

24. Sal Romano

Easily one of “Mad Men’s” most tragic figures, and an essential element of the show’s earlier years. Sal’s homosexuality might have been obvious from his very first scene in the very first episode of the show, but that’s just what made his presence so vital; any show about the 1960s has to be a show about sublimation and conformity on some level, and Sal lived that truth until his last appearance in Season 3. Every season since, we’ve waited for a hint of what happened to Sal — probably in vain. But who knows what might happen in a series finale, especially when it comes to “Mad Men.”

23. Mona Sterling Pike

Mrs. Roger Sterling No. 1, for sure (and not just because she was played by John Slattery’s real wife, Talia Balsam). Aside from her completely understandable frustration over the whole “husband leaves you for a secretary” thing, Mona was a totally chill customer. It would be hard not to love Mona a little bit.

22. Dawn Chambers

Best miniskirts. Toughest job in the office.

21. “Smitty” Smith and Kurt Smith

Partners at the beginning, partners (as far as we know) to the end. And you know what? That coffee jingle of theirs was pretty great.

20. Ida Blankenship

“She was born in 1898 in a barn. She died on the 37th floor of a skyscraper. She was an astronaut.” Also, she was a hellcat in the sack. Rest in peace, Mrs. Blankenship (with Harry’s afghan).

19. Carla

Her firing at the end of Season 4 was just one moment in the swirling chaos of upheaval, but while never again really mentioned, it remains a tragedy. Even Henry, a relative stranger at that point, knew her importance to the family. She deserved better.

18. Freddy Rumsen

At the very least, Freddy was the one who gave Peggy a chance. At the very most, he was a man dedicated to his craft (if not monumentally talented) and, once he got sober, a man who genuinely cared for his fellow man. Anyone who doesn’t have a hint of a soft spot for Freddy doesn’t understand human compassion. Way to go, Freddy.

17. Bob Benson

God, it took forever for Matt Weiner to give it up and reveal that yes, Bob Benson was a closeted gay man. But there was something rather beautiful and poignant about his struggle — that is, Matt Weiner’s struggle to make it seem like Bob Benson’s secret was anything other than being secretly gay. But also, Bob was awfully sweet with Joan. And those shorts!

Team Bob.

16. Michael Ginsberg

Would Ginsberg have gone out on such a crazy note had Ben Feldman not had an NBC sitcom waiting for him? No clue. But arguably the most brilliant pure creative to work under the Sterling Cooper name was one of the show’s most fascinating characters.

15. Henry Francis

He might have fallen in love with a married woman. He might have been (egads) a Republican. But he was a fundamentally good guy who genuinely loved his second wife, and Betty was ultimately a lot happier with him than she was with Don.

14. Ted Chaough

God, the whole “guy falling in love with his protege” thing ended up dragging the character down on a number of levels, but when he and Don worked with — and not against — each other, it was pretty cool. Don Draper would never open his process up to true collaboration, really, but if he had, Ted would have been worthy.

13. Betty Hofstadt Draper Francis

Oh, Betty. Frustrated, ambitious, intelligent, bitter, shallow, angry… Betty Draper Francis encapsulated so much honest vulnerability over the show’s seven seasons that even in her darkest moments, you still understood her as a human being in search of understanding and love. The kind of person easily warped by her surroundings, Betty has nonetheless avoided feeling static, at least since the end of her marriage to Don. She was one of the show’s most iconic characters, and beautiful up until the very end.

12. Stan Rizzo

Being in love with Stan is weird because it involves trying to deduce why, exactly, you are in love with him. Is it the beard? The fringed jacket? The way he treats Peggy, on balance, as an equal he respects? Maybe, maybe… Or maybe it’s just his inimitable “don’t give a fuck gonna do my best” approach to a job that’s crumpled lesser men. Whatever it is, we love Stan. Stan is the man.

11. Meredith

Before Season 7, we might not have even remembered her name. But in the show’s final episodes, Don’s chirpy little secretary became a genuine MVP, keeping her boss in line while also managing external expectations and adding positive energy and humor to some pretty dark storylines. Meredith should get everything she ever wants. Meredith for McCann Erickson CEO. MEREDITH FOR PRESIDENT.

10. Sally Draper

We’re probably going to be watching Kiernan Shipka on screen for decades to come. (She’s just so good.) And decades from now, we might remember, “Wow, we watched her grow up on screen. We watched her become an incredible talent right in front of our eyes.” And while Sally Draper, as a character, plugs pretty firmly into an “angry teen girl” trope, Shipka was never anything less than fully possessed and incredibly dynamic.

9. Trudy Campbell

Maybe one of the most genuinely decent people on this show, but also baller as hell. Hell’s bells, Trudy.

8. Ken Cosgrove

Ken was the true poet of Sterling Cooper and unappreciated in his time. The revelation of his talents as a fiction writer made him fascinating after his initial introduction as another white male bore, and as he delved into his craft, he only became more interesting. Alas, his Season 7 decision to abandon a chance at real pure happiness in exchange for vengeance against his former employer, has him lower on this list than initially anticipated. However, we still love him as a writer; it’s just frustrating, to see someone with talent choose a different path. 

7. Anna Draper

Imagine what might have happened if the pot-smoking, polio-hobbled Mrs. Draper No. 1 (in all respects) had been born in modern times. Imagine the worlds she would have conquered. Even as a “widowed” piano teacher living a quiet life in Santa Ana, she was dynamic and beautiful and fearless. Anna Draper deserved better than her century.

6. Pete Campbell

Descended from royalty. Fighting a constant battle with personal dignity. Sometimes failing. Sometimes awful. But weirdly, not incorrect about a lot of the stuff that truly matters. It’s hard to sum Pete up in just a few words. So let this GIF do the work for us.

5. Bert Cooper

Bert always felt like something of a deliberate enigma, but that never made him anything less than a beloved figure. His loss was keenly felt, and his legacy is eternal.

4. Joan Hollway Harris

In interviews leading up to the final episodes, Christina Hendricks commented that she was “such a fun, bitchy, sassy girl” during her early episodes. Even then she was still a mesmerizing force on screen, one who only became more compelling after evolving into a true human being. Joan was majestic. Joan was fierce. Joan still makes me cry when I rewatch the episode where she discovers a job she’s brilliant at — covering TV for Harry Crane — and it’s cruelly ripped away. Despite all her bristle, all her edge, Joan was great.

3. Roger Sterling

“Mad Men” without Roger would be like a martini without olives — or without vodka, for that matter. The shape would remain, but the flavor? So lacking. The thing that’s kind of incredible about Roger as a character is that he never, ever stopped being likeable. He might, in fact, be the only white man in the “Mad Men” credits to own that honor. Born of privilege, luxuriant of mustache in the show’s final days, Roger Sterling was singular, both as a man and as a character on television. Let us remember him at his best.

2. Don Draper

Don is so much the heart and soul of this show that for seven seasons, people have been convinced the show will end with him jumping off a building because that’s what the faceless automaton in the opening credits does. But Don’s fate, at this point, is far more uncertain. Far more complex than just a faceless automaton. Far more fascinating. And that matches with our understanding of the character, a man who was always profoundly interested in escaping the limitations of the expectations placed upon him. Don Draper has always been a man operating behind some sort of facade, but when you think about the way in which we all confront the world, that facade just feels like an extension of the normal human experience. Don was always, always hiding something — just like every single other person on the planet — which is why he became our icon and stand-in. We might not all look like Jon Hamm. But, on some level, all of us can understand what it’s like to be Don Draper; pretending to be someone we’re not.

1. Peggy Olson

Here’s the thing. “Mad Men” is a show built on surprise, and unexpected shifts in the social order. And as much as “Mad Men” was a show about Don Draper, Peggy has always been there, in her beautifully flawed, brilliant glory. Peggy, from the very beginning, fought battles that would crush any average person. Peggy was a goddamn gladiator, smart and determined and capable of badassery on a level television may still not understand. While Don was someone born of the past, Peggy was the future. As Season 7 of “Mad Men” could not help but remind us, it’s the future we look to, always.

The series finale of “Mad Men” airs Sunday at 10pm on AMC.

READ MORE: Why We Shouldn’t Be Guessing the Ending of ‘Mad Men’

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