20) Anna Draper
Played by: Melinda Page Hamilton
First Appearance: “The Gold Violin” (Season 2, Episode 7)
Dick Whitman hit the identity theft jackpot with Don Draper. Not only was the real Mrs. Draper willing to let Dick keep up the sham, but she would grow to be one of his closest and truest friends. In Don’s own words, Anna was the only person who ever really knew him, and she represents all the better angels of his nature that get buried by booze and ennui. Kind, optimistic, and compassionate, Anna is so sanctified that even her untimely death comes with the implication that she’s moving on to a better existence. Her ghostly appearance in “The Suitcase” should be ridiculous, but it makes for one of the most eerie and unforgettable images of the entire series.
19) Harry Crane
Played by: Rich Sommer
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Harry’s evolution into perhaps the most obnoxious person at SC&P is an achievement built out of small beginnings. As just a simple media buyer, he started off as one of the more tolerable suits at the office. But shortly after he got his hands on the television department, the power started going to his head. He’d cock-up using that power in ways that were often embarrassing and laughable, and part of you has to admire Harry’s ability to bounce back from every self-inflicted humiliation. But the greedier and seedier he became, the more comfortable he felt throwing his weight around the office. The innocuous Harry Crane of old was eventually subsumed by one no less foolish, but certainly more entitled. When Jim Cutler calls Harry the most dishonest person he’s ever met, you know there’s no hope for the guy. At least he’s McCann Erikson’s headache now.
18) Rachel Menken
Played by: Maggie Siff
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
The only client Don ever got into bed with, Rachel had to battle against many preconceptions as the head of Menken’s Department Store. As a single, business-minded Jewish woman, respect for her was based on inherited wealth, and earned by being more demanding and assertive than was considered acceptable at the time. It’s no wonder Don became captivated by her, and though she eventually proved the feeling was mutual, she was also smart enough to jump Don’s sinking ship at the first sign of trouble. Doing so meant that her unexpectedly short life was spent shared as part of a real family, instead of just Don’s escape plan.
17) Bob Benson
Played by: James Wolk
First Appearance: “The Doorway, Part 1” (Season 6, Episode 1)
One-season wonders don’t get more memorable than James Wolk as Bob Benson, the mysterious, ingratiating junior account man. Better at greasing wheels than Pete, and with more secrets to hide than even Don, Bob spent most of Season 6 as an object of office and audience suspicion. Even as he worked to diffuse coworker tension, or lend Joan a helping hand, you kept wondering what the guy’s endgame ways. Turns out (assuming he didn’t conspire with Manolo to off Pete’s mom) Bob was just as clean-cut and friendly as he appeared, just with a falsified background, and a sexual orientation that put his job at risk. That Wolk couldn’t stick around to further detail Bob’s backstory seems a missed opportunity, but as a walking enigma, Bob, and his short-shorts, left a lasting impression on Mad Men.
16) Stan Rizzo
Played by: Jay R. Ferguson
First Appearance: “Waldorf Stories” (Season 4, Episode 6)
One of the most fruitful additions to Mad Men: The New Class, Rizzo replaced Sal as the agency’s art director when it moved to the Time and Life building, but played a very different role on the show. Stan started as a sexist blowhard for Peggy to butt heads with, but their interactions quickly developed into one of the sweetest friendships of the series. Once he toned down on the braggadocio (and started growing his awesome beard), Stan became a great utility character, both as a slacker wingman to Ginsberg, and encouraging shoulder for Peggy. He was one of the few people at SCDP who seemed to enjoy what he did for a living, and the positive attitude was often infectious.
15) Megan Calvet
Played by: Jessica Paré
First Appearance: “Christmas Comes But Once a Year” (Season 4, Episode 2)
Warm and hip where Betty was frigid and traditional, Megan gave Don a second wife as unlike his first as humanly possible. Too bad he was the same Don, so the moment she expressed an ambition in something other than homemaking or advertising, he started checking out. Working against Megan were acting skills that rarely rose above “soap opera worthy,” and youthful inexperience that made her prone to bouts of entitlement and melodramatic self-pity. Also, she had a really weird thing for spaghetti. It’s a little detail, but the woman was always five minutes away from serving, or offering to make pasta.
Anyway, she got along great with Don’s kids, and did her best to keep her marriage together while pursuing a career of her own. The show’s interest in Megan seemed to fade with Don’s, but she had her fair share of great stories, whether saving the Heinz account over dinner, or bringing the earworm that is “Zou Bisou Bisou” to viewers everywhere.
14) Ted Chaough
Played by: Kevin Rahm
First Appearance: “The Chrysanthemum and the Sword” (Season 4, Episode 5)
Ted’s arc is an odd one. He’s introduced as a cocky rival to Don, regularly calling him out before Don even knows who Ted is. Maybe getting tricked by Don into embarrassing himself in front of Honda gave him the gift of humility, as by the time Peggy joins CGC, he’s possessed by a much smaller ego. Still competitive with Don when they’re both chasing Chevy, Ted jumps into bed with him all the same, and SC&P is born.
Ted’s presented as being a pretty copacetic guy (“groovy,” as he might say), and his blossoming romance with Peggy starts promising…until you remember he has a wife and two kids. By the time he’s moved out to California, what love for advertising he ever had is all gone, only to be reinvigorated by the McCann Erikson purchase. Rather than being existentially exhausted by his work like Don, Ted ends up a carefree cog in someone else’s machine, which is about as close to a happy ending as we can expect for anyone on Mad Men.
13) Michael Ginsberg
Played by: Ben Feldman
First Appearance: “Tea Leaves” (Season 5, Episode 3)
The Sterling Cooper of 1960 wouldn’t have let a screwball like Ginsberg in the door, let alone apply for a job. Even by 1966, his extroversion nearly prevents him from getting a gig as a part-time copywriter. But Ginsberg quickly established himself as one of the deftest creative minds at SCDP, cracking the Jaguar campaign wide open, and submitting work good enough to make Don jealous. The seeds of Michael’s eventual mental breakdown were planted early in “Far Away Places,” his unfiltered demeanor seemingly a coping mechanism from his tragic upbringing. Ginsberg contributed many distinctive lines and moments to Mad Men’s history, so much so that his departure last year felt almost premature. Then again, being taken away in a stretcher because you gave your boss your amputated nipple is one hell of a way to go.
12) Trudy Campbell
Played by: Alison Brie
First Appearance: “New Amsterdam” (Season 1, Episode 4)
From the minute you discover what a spineless worm Pete Campbell is in Mad Men’s pilot, you feel bad for the unseen woman that’s agreed to marry him. What’s amazing about Trudy is how she shucked the charity case designation, and instead became a woman who knew what she wanted, and how to get it, despite her husband’s failings. Trudy was a natural fit for home life, but proved more ruthless than her husband when it came to protecting the family’s future. Pete should have known that stepping out on Trudy was like running with scissors. Her evisceration of Pete in the divorce was satisfying, but that the two have reconciled somewhat over the years shows there’s a real bond between the two extending beyond a shared appreciation for the Charleston.
11) Salvatore Romano
Played by: Bryan Batt
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Sterling Cooper’s dry and dapper art director, Sal is about the only creative entity at the old office that Don doesn’t ritually abuse. Perhaps it’s his age, or his talent, but the mutual respect between the two is almost certainly what made Don look the other way when he found out Sal was gay. Of course, Don threw all that respect out the window when Sal refused to sleep with Lee Garner Jr., swiftly illustrating why it is Sal struggled with his orientation for so long. Despite his success as the agency’s art man and aspiring in-house commercial director, Sal’s unexpected early exit has made his potential return something Weiner has had to shoot down in interview after interview. Next time, maybe don’t strand one of your most sympathetic and unique characters in a phone booth, Weiner!
