100) Dick Whitman
Played by: Brandon Killham, Jake Radaker, Jon Hamm
First Appearance: “The Hobo Code” (Season 1, Episode 8)
Okay, so we’re starting with a technicality here, but there’s a good reason: the flashbacks to Don Draper’s childhood are culturally and empirically proven to be bad. Whether it was Dick’s cathouse misadventures, or the show trying to pass off 37-year-old Jon Hamm as a fresh-faced military recruit, the flashbacks proved there was a limit to our interest in explaining Don Draper. Therefore, pre-Don, and by extension, most of the rest of the Whitman clan, have the honor of officially being The Worst. Please come to the podium to accept your commemorative Horseshoe of Overt Symbolism.
99) Polly (The Dog)
Played by: A dog
First Appearance: “Marriage of Figaro” (Season 1, Episode 3)
Who’s a good girl?! Who was impulsively purchased by Don as an apology for bailing on his daughter’s birthday party?! Who ate one of the neighbor’s pigeons?! Who got banished to the basement after Betty and Don’s divorce because Henry’s a big jerk?!
98) Jennifer Crane
Played by: Laura Regan
First Appearance: “Flight 1” (Season 2, Episode 2)
Harry Crane’s long-suffering wife, in that being married to Harry Crane is a burden no woman should have to bear. Initially, the Crane marriage appears to be one of the stronger ones on the show, but as Harry’s infidelity and general asshole-ry got out of hand, she receded into the background.
97) Jonesy
Played by: Ray Abruzzo
First Appearance: “The Doorway, Part 1” (Season 6, Episode 1)
Jonesy is the doorman in Don’s building. He almost died that one time. It was really scary for Don. But Dr. Rosen saved him! Keep up the good work, Jonesy!
96) Cynthia Cosgrove
Played by: Larisa Oleynik
First Appearance: “Chinese Wall” (Season 4, Episode 11)
Cynthia. Cosgrove. Ken’s wife? Okay, probably doesn’t ring a bell. There was a whole running gag in “Signal 30” about Don and Megan trying to get through a Cosgrove dinner party while unable to remember their hostess’ name. But she seems like a generally well-adjusted person, and tried to guide Ken back to his writing career after it had taken so much from him.
95) Howard Dawes
Played by: Jeff Clarke
First Appearance: “A Little Kiss, Part 1” (Season 5, Episode 1)
Insurance salesmen aren’t especially likable. Philandering insurance salesmen even more so. And philandering insurance salesmen who have their wives committed for shock therapy? Forget about it. Until recently, Howard Dawes had the distinction of being the only man to enter a fight with Pete Campbell where we hoped Pete would be the winner.
94) Moira
Played by: Christine Garver
First Appearance: “For Immediate Release” (Season 6, Episode 6)
Ted Chaough’s secretary is defined by a fierce loyalty to Ted aaaaaand….not much else. When your most memorable moment is being snippy with Peggy, you’re not really standing out from the herd. That she hasn’t been seen around the office in more than a year suggests that her devotion to Ted wasn’t reciprocated.
93) Dr. Arnold Wayne
Played by: Andy Umberger
First Appearance: “Ladies Room” (Season 1, Episode 2)
Betty’s shrink and Don’s snitch, Wayne had about as much going on in his life as the man himself had respect for doctor-patient confidentiality. Even though he was a fink (and a bit of a perv), at least his involvement in Betty’s life opened her up to the idea of getting Sally some counselling, and pursuing a psych degree of her own.
92) William Hofstadt
Played by: Eric Ladin
First Appearance: “The Inheritance” (Season 2, Episode 10)
William’s an impressive figure, insofar that proving Betty isn’t the worst Hofstadt child is something of a feat. Petty, selfish, and just an all-around ingrate, William is actually worse for having married Judy, who seems perfectly nice otherwise. Just let him have your dad’s house, Betty! (Then burn it down).
91) St. John Powell
Played by: Charles Shaughnessy
First Appearance: “The Jet Set” (Season 2, Episode 11)
The connective surname in Putnam, Powell and Lowe, the British firm that bought Sterling Cooper back near the end of Season 2. He mostly just told Lane what to do from across the pond, and conspired to have the Sterling Cooper-enhanced PPL sold to McCann Erikson. He also stands out because of the peculiar way Lane would pronounce his name (Sin-jin? Sen-jin? It’s probably some British-ism).
