50) Jane Siegel
Played by: Peyton List
First Appearance: “The New Girl” (Season 2, Episode 5)
Jane’s rap sheet does not tell a particularly flattering tale. She constantly butted heads with Joan. She gave Roger an incentive to breakup his family. She thinks blackface routines are hi-larious. But Jane was young, naïve, and vulnerable to the charms of Roger Sterling. Can you blame her? At least she had some cool friends who helped start Roger on the path of self-discovery through hallucinogens. And she busted into Bert Cooper’s office once to check out his fancy new painting. That takes serious baitsim.
49) Bobbie Barrett
Played by: Melinda McGraw
First Appearance: “The Benefactor” (Season 2, Episode 3)
Arguably the more obnoxious half of the Barrett duo, Bobbie proved to be the most unpredictable and destructive of Don’s extramarital interests. She’s a pretty decent manager, and knows a good/bad TV title pun when she thinks of one (Grin and Barrett). When it comes to matters of discretion, though, she’s two fingers of trouble. In a sense, it’s a good thing she came along, as it seemed as though Betty would need someone as careless as Bobbie to finally get wise to Don’s infidelity.
48) Herb Rennet
Played by: Gary Basaraba
First Appearance: “The Other Woman” (Season 5, Episode 11)
Ugh. The jag-off from Jaguar, Herb was responsible for ensuring upstart SCDP had a car to call its own…so long as he got to spend a night with Joan. She got a partnership out of the deal, and SCDP had an account to keep them occupied until Chevy came around, but Don selfishly flushing the account just to get rid of the skuzzball was good riddance to bad business. Let’s hope we haven’t seen his ugly mug since because his wife Peaches had him mauled to death by her puppies.
47) Richard
Played by: Bruce Greenwood
First Appearance: “The Forecast” (Season 7, Episode 10)
Had he not walked into Joan’s life so late in Mad Men’s run, Richard would be on track to place much higher in the rankings. He made a not-so charming fuss over Joan having a kid, but he was also smart enough to realize what an idiotic thing to do that was. This is Joan we’re talking about, bud. Joan. All things considered, Richard’s a catch: he’s well off, attentive, and looks like Bruce Greenwood. And he knows “a guy,” in case you ever need your lecherous boss taken care of. We like you Richard – don’t betray our trust in the finale. And for God’s sake, let Joan start picking out your wardrobe.
46) Caroline
Played by: Beth Hall
First Appearance: “Christmas Comes But Once a Year” (Season 4, Episode 2)
Oh, sweet, perfectly adequate Caroline. You were never the brightest secretary, nor the most reliable. Roger, in his own words, kind of hated you. But we love your unflappability, your commitment to getting through the day at your own pace, and not letting SCDP chew you up and spit you out the way it has so many others.
45) Lee Garner Jr.
Played by: Darren Pettie
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
As the heir to the business that made-up more than half of Sterling Cooper’s billings for most of its lifespan, Lee turning heel was less a question of “if” than “when.” Those who inherit great wealth on Mad Men often turn out to be morons or bullies, and Lee is most certainly in the latter camp, forcing Sal’s firing when he didn’t return Lee’s advances, and humiliating Roger at the office Christmas party. But the firm, and Roger could look back and laugh at the guy (including that time Roger had to hold his balls) once Lee took his cancerous toys to another sandbox.
44) Conrad ‘Connie’ Hilton
Played by: Chelcie Ross
First Appearance: “My Old Kentucky Home” (Season 3, Episode 3)
As a sort of surrogate father figure, Connie gave Don something to aspire to: he was respected, introspective, yet never without purpose. Connie himself liked Don enough to call him a son…for a time. The longer their relationship wore on, the clearer it became that Connie was just as insufferable as any other client, the difference being that Connie didn’t just want the moon from Don, but believed he deserved it.
43) Alice Cooper
Played by: Mary Anne McGarry
First Appearance: “The Mountain King” (Season 2, Episode 12)
Barely squeaking in thanks to a wordless second appearance in Season 3’s “The Color Blue,” it would have been worth bending the rules anyway for Bert’s younger sister Alice. As secretary treasurer of the company, Alice was instrumental in getting Sterling Cooper to accept the PPL takeover. In her three scenes from “The Mountain King,” she gets in more digs at Roger and Bert than others would dare attempt in a lifetime, suggesting that Sterling Cooper was long operating without its craftiest and classiest partner.
42) Kurt Smith
Played by: Edin Gali
First Appearance: “For Those Who Think Young” (Season 2, Episode 1)
As part of the brat pack hired to youth-inize Sterling Cooper, Kurt is just the cool version of Smitty. He’s European, he goes to Bob Dylan concerts, and is totally chill about his sexual orientation (even if nobody else is). More importantly, he gave Peggy the Haircut of Power that would help define her look during her rapid rise through the agency. You were too good for Sterling Cooper, Kurt!
41) Katherine Olson
Played by: Myra Turley
First Appearance: “Flight 1” (Season 2, Episode 2)
Though mama Olson’s presence usually meant Peggy was due for a motherly haranguing, Katherine did bring out the Brooklyn accent in her daughter, which was always a treat to hear. A bit of a devout diva, Katherine was as old-fashioned as they come, and was better as being a uniting nuisance for the Olson sisters than a bedrock of support for her daughters. Still, whether bossing around Father Gill, or reacting to Peggy living in sin, Katherine was a scream…so long as she wasn’t your mother.