10) Lane Pryce
Played by: Jared Harris
First Appearance: “Out of Town” (Season 3, Episode 1)
Lane was no doubt honored to be the only employee from PPL to make the transition from Sterling Cooper to SCDP, but staying with the agency would ultimately lead him to end his life. Lane may have been stodgy, but he was one of the few guys who seemed satisfied with the good life when it presented itself. Granted, all it took were some marital and financial troubles for him to pursue an affair and commit fraud, but Lane’s mostly-chivalrous conduct is what made him likeable, if completely unfit for the advertising business.
In his time, he did manage to knock Pete out in a boardroom boxing match, and his failed suicide-by-Jaguar remains one of cleverest moments in Mad Men history. His death in “Commissions and Fees” cast a pall over the remainder of Season 6, and much of the rest of the series, but its because of his timid exterior that he was able to surprise you so often. If you had to choose someone in the office to get wasted with and watch a Godzilla movie, would it be Lane? No, and that’s why you’d be missing out.
9) Ken Cosgrove
Played by: Aaron Stanton
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
“You look like a spy,” Roger Sterling recently said of Ken Cosgrove. Indeed, Ken has many spy-like qualities, including numerous aliases (Ben Hargrove and Dave Algonquin being his nom de plumes), a few secret talents, and an unfortunate tendency of having guns pointed/shot in his face. His likely homophobia aside, Ken might be the single nicest guy to ever work at Sterling Cooper (and almost certainly McCann Erikson). He promised to help piggyback Peggy onto any career moves he might make, is loyal to his wife, and exceeds as an account man without resorting to the nepotism Pete relies on. It’s what makes his eventual heel-turn at the end of the series both incredibly satisfying, and thoroughly dispiriting. An eye for an eye isn’t a healthy attitude to endorse, but the only way Ken’s long-delayed revenge could have been any sweeter is if he had tap danced out of that last meeting with Roger and Pete.
8) Bert Cooper
Played by: Robert Morse
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
The guiding hand of Sterling Cooper was a rather peculiar specimen, as Bert Cooper’s mind for business seemed to run counter to his many eccentricities. Sure, he loved Ayn Rand, and bought paintings for resale instead of artistic value, but senior partners with a fetish for Japanese culture and open-toe footwear are a rarity. Even for someone his age, Bert had the air of a man wise beyond his years (if still behind the times on matters of race), dispensing erudite wisdom and amused commentary like a Madison Avenue Yoda. His passing in “Waterloo,” while sad, gave us one of Mad Men’s greatest flights of fancy, a soft shoe number by Bert reminding Don that the best things in life are free. So bravo to you, Bert Cooper, you weird, wonderful, testicle-less creature.
7) Betty Hofstadt Draper/Francis
Played by: January Jones
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
There’s no Team Betty. Even people who openly support the character often do so at arm’s length. Betty, and January Jones’ performance of her are withholding, and seemingly limited. As the mitochondrial ancestor to AMC’s brand of divisive wives, Betty could be viewed simplistically as a shrew and a harpy, particularly as later seasons of Mad Men seemed to struggle to find a use for her. But during those first three seasons, and particularly this last one, Jones and the writers brought a lot of depth to Betty as she learned to view herself as more than just a daughter, or a housewife. The last season of Mad Men has been about rising above life’s disappointments, and finding graceful acceptance of what you’ve been given. Few made that lesson feel as earned as Betty, and learning to embrace her made for one of Mad Men’s toughest, but ultimately most rewarding demands.
6) Sally Draper
Played by: Kiernan Shipka
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Even when comparing where Don, Peggy, and the rest of New York were in 1960 versus where they’d be by 1971, it’s no surprise that a kid growing up during that period would come out the other end the most radically changed person. What maybe is surprising is how gradually Sally Draper turned into one of Mad Men’s best characters, and Kiernan Shipka one of its best performers.
As she wrestled with Don and Betty’s divorce, and the terrifying prospect of really being her parents’ daughter, Sally experienced an upbringing not as insulated as her mother, or hard-luck as her father. She could be a naïve brat just as easily as she could be an unexpectedly mature and sensitive adolescent, and Sally came to embody the real legacy that her parents, and their generation were going to leave behind. So many shows ignore or simplify their teenage characters, but Sally’s journey through Mad Men was one of constant discovery and growth.
5) Pete Campbell
Played by: Vincent Kartheiser
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
“Not great, Bob!” “The clients want to live too, Ted!” “The king ordered it!” All worthy entries on any list of memorable TV outbursts, and all owed to one Peter Campbell. That our memories of Pete are so often dominated by small moments of comic indignity ignores the markedly different man Pete became over the course of the series. As a toady Don-wannabe who knocked up Peggy before marrying Trudy, Pete was the first season’s most loathsome regular. Over the course of the series he did many awful things in his personal and professional life, but rather than judging him, Mad Men often viewed Pete with a sense of great pity.
Despite his exceptional (if sometimes underhanded) business acumen, he was a perpetual office whipping boy – not that we didn’t delight in watching Roger and company knock him down a peg on the regular. Eventually, most viewers warmed to Pete because he, unlike many other characters, seemed to learn from past mistakes. In the end, Pete made peace with how different from Don he was, and was all the better for it. Besides, it’s not like Don could ever do a pratfall this incredible.
4) Joan Holloway
Played by: Christina Hendricks
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Queen B of the office, Joan’s career can be viewed as an unstoppable success story. From young divorcee, to secretary, to office manager, to Madison Avenue partner in less than twenty years, Joan’s C.V. reads as confidently as her exterior. Of course, both hide a much more complicated history and person than appearances let on. Even if she made running an agency and castrating office clods look effortless, big things in Joan’s life never came easy. Her son was made with a man other than her awful second husband, and getting a partnership rarely granted her the respect she struggled to achieve.
So many great scenes on Mad Men just needed to put Joan in a room with Roger, Don, or Peggy; sparks proceeding to fly was a given. But her own story is one of embattled perseverance through some of the worst harassment and mistreatment a woman in her position could face at the time. Joan’s a survivor, through and through, and that she made it to the finish line with a son she loves, a handsome new beau, and set for life is the least we should have expected for her.
3) Roger Sterling
Played by: John Slattery
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Has a more quotable TV character graced our screens since Roger Sterling first sauntered into Don’s office, and introduced himself as the gold standard of Mad Men repartee? He’s the sort of man you’d follow to hell and back – assuming the devil would let such a sharp-tongued conversationalist out of his company. Whether offering his well-sauced insights to any and all that would listen, or chasing women younger than some of the bottles in his magnificent office bar, Roger’s antics were worth keeping up with through every wisecrack and coronary.
Like many a handsome clown, though, Roger’s debauched exterior wore thinner and thinner with each year, as new marriages and moments of clarity inevitably lead him back into another bar, or another bed. Roger may learn too late to appreciate what he has, rather than grasp at what he’s losing, but following him on his quest for fulfillment was one of Mad Men’s greatest pleasures. “Don’t you love the chase?” He once asked Don. When you led the way, Roger, we sure did.
2) Don Draper
Played by: Jon Hamm
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Don Draper is a prince. Don Draper is a monster. Don Draper is a visionary. Don Draper is a shyster. Don Draper is God’s gift to women. Don Draper is the world’s unloved son. He’s a man of wealth and taste, and the one on TV telling you how white your shirts can be. He’s Roger Thornhill and Rosemary’s baby, the man given a new identity that can’t escape his demons. He was a monument to one generation, and a relic to the next.
Over the run of Mad Men, the persona that was “Don Draper” gave way to the damaged, desperate man he though he’d left back in Korea. As his flaws became more evident to viewers at home and those around him, it became clear that the man called Don Draper was nothing more than a magic trick. People chose not to question Don’s charade for fear of finding themselves hiding behind the curtain. We know the illusion of this handsome, brilliant, unstoppable man isn’t real, but buying into Don Draper means buying into the idea that anyone can really be okay. Where Don will finally end up remains a mystery. Where he’s taken us is through one of the most mystifying, revealing, and contradictory lives in TV history.
1) Peggy Olson
Played by: Elisabeth Moss
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
Hail Margaret, full of grace. Look, if the above paragraph says anything, it’s that we all want to be Don Draper – at least, the version of him that Don kept up, before slowly shedding the identity like a snake’s skin. But that guy doesn’t exist. At our best, most of us can just try to be Peggy, someone given a life without expectations, but damned if they’re going to let it go to waste. She’s far from a perfect person, subject to the same insecurities and foibles as anyone else. That she routinely found success in spite of those faults, and sexist institutional structures, made every win for Peggy a win for the underdogs.
Few of us will ever have the luxury of Don’s comfortable odyssey into solipsism, but Peggy fought tooth and nail for every inch of the life she made, mistakes and all. It wasn’t always roller-skating and slow dances with Don, but Peggy’s journey through Mad Men is the one you can point to as something worth aspiring towards. That being on that journey meant following a woman as willful, charming, brilliant, and human as Peggy made her not Mad Men’s most iconic character, but its best.