70) Stephanie Horton
Played by: Caity Lotz
First Appearance: “The Good News” (Season 4, Episode 3)
Like Margaret, Anna Draper’s niece was a straight arrow that wound up a flower child. As Don’s last living connection to his past, the sexual tension between the two was certainly in keeping with Don as we knew him, but she, like Anna, was one of the few people Don could ever be his real self around.
69) Dr. Arnold Rosen
Played by: Brian Markinson
First Appearance: “The Doorway, Part 1” (Season 6, Episode 1)
One of the few guys Don’s gotten to know well enough to properly cuckold, Dr. Rosen seemed blissfully unaware of the fact that his apartment pal was running around with his wife. Don’s affair with Sylvia is all the more a betrayal because Dr. Rosen is someone Don actually seems to respect. Few professionals make you unsatisfied with your achievements quite like a doctor can, and though Arnold wasn’t the most charismatic sort, he’s the guy who’ll ski through a New York blizzard just to get the job done.
68) Burt Peterson
Played by: Michael Gaston
First Appearance: “Out of Town” (Season 3, Episode 1)
Whether making late night calls in his undies, or being subjected to serial firings by Roger, Burt Peterson made for as good a piñata as Mad Men ever had to offer. “Fellow comrades in mediocrity,” this titan of mid-tier creative once roared, “I want you to listen very carefully. You can all go straight to hell.” You too buddy. You too.
67) Ferg Donnelly
Played by: Paul Johansson
First Appearance: “Severance” (Season 7, Episode 8)
Jim Hobart’s chief underling and McCann Erikson’s resident (terrible) impressionist, Ferg looks and acts like a shaved gorilla. He’s all glad-handing and smiles one minute, and the next he’s making advances at Joan while holding her job hostage. We knew McCann Erikson was going to be hell, we just didn’t expect guys like Ferg were capable of living down to such low expectations.
66) Allison
Played by: Alexa Alemanni
First Appearance: “Marriage of Figaro” (Season 1, Episode 3)
A longtime hanger-on in the office until rising to some prominence in Season 4, everything you need to know about Allison can be summed up in the title of her last appearance: “The Rejected.” In her defense, Don, in the throes of post-divorce self-destruction, did everything in his power to ignore the fact that they slept together. But she’s also the sort of person who finds it difficult to call an obvious prick like Don “not a good person.” Sadly, she wasn’t cutout to be Don’s secretary. At least we can thank her for inspiring one of the show’s silliest visual gags.
65) Ed
Played by: Kit Williamson
First Appearance: “The Doorway, Part 2” (Season 6, Episode 1)
As far as office third-stringers go, Ed was pretty A-OK. He and Mathis proved useful enough to Peggy that she was able to keep them after the SCDP/CGC merger. He didn’t have his pal’s knack for glorious self-immolation, but left the agency with a bit of dignity, and a lot of free phone calls. And he’s a Japanese-speaking Mets fan? Shame you only got so interesting at the very end, Ed.
64) John Mathis
Played by: Trevor Einhorn
First Appearance: “The Doorway, Part 2” (Season 6, Episode 1)
Ed’s partner in obscurity, Mathis was able to comfortably coast in the background for a good long while. His exit was more spectacular than any of his work, as his blaze-of-glory exit from SC&P was a dressing-down of Don that only a guy on a suicide mission could afford. He worked like a drone, but went out like a (still pretty idiotic) champ.
63) Pauline Francis
Played by: Pamela Dunlap
First Appearance: “Public Relations” (Season 4, Episode 1)
Henry’s battle-axe of a mother, Pauline’s disapproval for her son’s divorce is second only to her contempt for his new wife. Pushy, abrasive, and over-eager to play the “my son’s very important” card, Pauline is not without her charms. “Mystery Date” saw her and Sally falling asleep to the news of the Richard Speck murders, Sally under the couch, and Pauline on guard duty with a paring knife in hand. Clearly, Pauline is to be underestimated at your own peril.
62) Helen Bishop
Played by: Darby Stanchfield
First Appearance: “Ladies Room” (Season 1, Episode 2)
Remember in Season 1 when a divorcée on the block was all anyone could talk about? Remember that her name was Helen Bishop? In retrospect, you wonder if there was once a version of Mad Men where Helen did more than just bring the big D-word to Ossington. Long-term, her contribution to the show was Glen more than anything, but at least we’ll always have Betty’s supermarket slap from “Red in the Face” to remember her by.
61) Jimmy Barrett
Played by: Patrick Fischler
First Appearance: “The Benefactor” (Season 2, Episode 3)
The standup who never learned the value of knowing when to shut up, Jimmy made his living by having a mouth big enough to stick both feet in. That people seemed to love him for this bedevilled Don, who often had to cleanup after Jimmy’s messes. Jimmy put the “Utz” in “putz,” but you kind of have to appreciate the guy’s quick wits –who among us could come up with a wisecrack in the split-second between getting punched by Don Draper, and recovering from getting punched by Don Draper?