The 18 Best Minor Mad Men Characters, Ranked by Awesomeness

by | April 4, 2015 | Comments

One of the early, indelible images from the first season of Mad Men didn’t involve any of the main cast members. Instead, it was a shot of a cigarette-smoking pregnant woman, a minor neighbor character. Did she matter? Yes, she did, but not because a story arc hinged on her; she mattered because details are the meat of this show. Over the seasons that followed, that approach came to mean a deep bench of supporting characters, and even one-off players, who delivered as much punch as the main cast. You can watch and re-watch, and you’ll find that the people in the margins are giving you everything. Here are our favorites:

18. Francine Hanson (Anne Dudek)

Francine is that pregnant smoking woman, and she’s the world’s best neighbor. She’s always up for gossiping with Betty (January Jones) about the neighborhood’s lone divorcée, Helen Bishop. The camera loves it when she smokes – commonplace in 1960 — luxuriating in the casual horror of it all. Best, Francine knows her husband is cheating on her, and she dreams of poisoning him for it, but she simply starts feeding him more instead. Problem solved.

17. Anna Draper (Melinda Page Hamilton)

On a show full of unhappy people, Anna Draper is a kind-hearted infusion of goodness. The widow of the real Don Draper, whose identity was stolen by Dick Whitman/fake Don (Jon Hamm), she nevertheless becomes his friend and one of his life’s few sources of genuine peace. When Anna dies of cancer, even her “ghost” lingers to comfort Don. He’s pretty much in her debt for all eternity.

16. Helen Bishop (Darby Stanchfield)

Never did a single thing wrong to anyone, but has the misfortune of 1) being divorced 2) being liberal 3) volunteering for the Kennedy campaign 4) taking scandalous walks alone, and 5) being Betty’s neighbor. When Helen politely asks Betty to stop being a total freak and giving locks of her hair to Helen’s unusual son Glen, Betty slaps her right in the middle of the supermarket. Poor Helen.

15. Midge Daniels (Rosemarie DeWitt)

Midge is a beatnik. She lives in the Village. She smokes weed. She reads Allen Ginsburg. She has lots of sex with Don. She is, in fact, the first of many, many women who will have lots of sex with Don. Don feels judged by her and her bohemian friends, then hypocritically dumps her for not truly loving him. In season four, she returns to ask Don for heroin money. This is a bummer, mostly because it allows Don to feel smug about being an alcoholic square.

14. Danny Siegel (Danny Strong)

Danny shows up at Sterling Cooper Draper Pryce with a laughable book, but they hire him anyway. He’s generally useless, but finds success later as a Hollywood producer (zing!) and takes to wearing really awesome hippie attire. Even better, the short-of-stature Danny turns heroic after he’s insulted by Roger Sterling (John Slattery), responding by punching his old boss right in the junk.

13. Lois Sadler (Crista Flanagan)

Lois is the most incompetent of secretaries. She moves from the switchboard to a desk, but that’s as much accomplishment as she can muster. She mistakes office-crush Sal Romano (Bryan Batt) for heterosexual. Then she gets fired by Don. Then she winds up back at the switchboard. Then she manages to become a secretary again. Then she accidentally runs over a man with a riding lawnmower – inside the office – destroying his foot.

12. Ida Blankenship (Randee Heller)

Ida is Bert Cooper (Robert Morse)’s salty, longtime secretary. Her age prompts Joan (Christina Hendricks) to assign her to Don in the interest of keeping Don’s fraternizing at bay. (Although Roger admits to an affair with Ida decades earlier: “The Queen of Perversions,” he notes.) Ida is old-world blunt in the midst of a smoothly neurotic modern office and dies at her desk. Bert’s eulogy: “She was born in 1898 in a barn. She died on the 37th floor of a skyscraper. She’s an astronaut.”

11. Jane Sterling (Peyton List)

If you’re going to marry your gold-digging secretary, like Roger Sterling does, then you could do worse than marrying Jane. She’s a straight shooter and doesn’t play games. She’ll encourage you to trip on LSD, and she’ll make you want to be a better man. And after she divorces you, she’ll still hang out and do you favors. For a price.

10. Mona Sterling Pike (Talia Balsam)

The gold standard of first wives. The long-suffering but sardonic former partner to Roger, Mona is pragmatic but concerned, holding her ex-husband’s feet to the fire, yet occasionally offering him comfort. She knows he’s a schmuck, she still cares, and her somewhat matronly fashion sense is impeccable.

9. Rachel Menken (Maggie Siff)

The Jewish head of a Manhattan department store that’s struggling to find its brand identity. She crosses swords with Don in a business meeting, which simultaneously angers him and turns him on. Then he takes her to dinner and tells her that love isn’t real and we all die alone. This turns HER on. They have a brief affair, but he can’t commit. Shocker.

8. Shirley (Sola Bamis)

Sterling Cooper Draper Pryce’s second black secretary, hired after Dawn (Teyonah Parris). Shirley’s skirts are shorter, her manners less timid, but she and Dawn have created a scathingly funny in-joke about their co-workers. It goes like this: Dawn greets Shirley with, “Hello, ‘Dawn.'” On cue, Shirley responds, “Hello, ‘Shirley.'”

7. Marie Calvet (Julia Ormond)

Megan Draper’s (Jessica Pare) acerbic mother. One-liner machine:
“Not every little girl gets to do what they want. The world could not support that many ballerinas.”
“This is what happens when you have the artistic temperament but you are not an artist.”
“She is the apple in the pig’s mouth!”

6. Sylvia Rosen (Linda Cardellini)

Moves into Don’s building. Holds her own with him when it comes to keeping track of the rules. But their affair is, by far, the show’s most dangerous. Proximity and passion and shared elevator rides with spouses equals whatever the opposite of NSA is. And then Don’s daughter, Sally (Kiernan Shipka), happens upon them in mid-well, you know. Like all of Don’s dalliances, it doesn’t go well.

5. Dawn Chambers (Teyonah Parris)

The character who breaks the race barrier at Sterling Cooper Draper Pryce, a token “equal opportunity” hire who quickly becomes a quiet, walking critique of the entire workplace environment. Dawn pays for being a pioneer, but she doesn’t break, even if the look on her face is, quite often, one of, “I will deal with this/I can’t believe I have to deal with this.” She starts out as Don’s secretary and eventually winds up in Joan’s old job, so she may yet have the last laugh.

4. Bobby Draper (Mason Vale Cotton)

Don doesn’t understand his daughter Sally, but his young son Bobby catches him off guard, tugging at Don’s negative perceptions of his own parenting. Bobby is rarely seen, but when he does show up, he inevitably says something accidentally poignant and unsettling. Anyone who can get under Don’s skin like this is on to something.

3. Glen Bishop (Marten Weiner)

Glen may be Mad Men‘s weirdest, most enigmatic character, a study in the progression of creepo male sexuality. He begins his tenure as a child, the stares-too-much neighbor boy who’s obsessed with Betty’s hair. He winds up a typical teenage boy — still staring too much — at private school with Sally.

2. Bob Benson (James Wolk)

Distractingly handsome and wholly mysterious, Bob Benson appears one day in the office, holding an extra cup of coffee for whomever wants it. Then he keeps doing that. He insinuates himself into lives and situations for his own benefit, and does so with so much skill and finesse that it (almost) never looks oily. He is the perfect stealth sycophant, and as his secrets unfold, so do his machinations. Wearer of very short shorts.

1. Joyce Ramsey (Zosia Mamet)

Joyce Ramsay doesn’t appear very often, but when she does, it’s gold. She gets Peggy Olsen (Elisabeth Moss) weed, helps her land a pantyhose account, and fascinates her with nonchalant lesbianism. Joyce’s deadpan cool and understated self-confidence light Peggy’s (non-sexual) fire; it’s like she’s been beamed in from the future to be Peggy’s power animal and teach her how Not Bothered a woman can be.

Dave White is the film critic for and co-hosts the Linoleum Knife podcast. Follow him on Twitter at @dlelandwhite.

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