The Madison Avenue staff of Sterling Cooper (and the family members they introduced us to) were quite the mixed bag of personalities from varied backgrounds, making Mad Men a surprise-a-minute to watch when they all interacted.
As much as fans often like being able to tell the good guys from the bad guys, this award-winning series was a heightened version of the reality of office life (spilling over into the characters' personal lives) where people are human. They acted in earnest in one situation, and then turned around and made a choice that caused upheaval from which none involved would ever recover. During the decade that was chronicled in the show (1960-1970), those characters that fans got to know over 92 episodes showed the best and worst of themselves, and fans loved them anyway.
10 Bertram Cooper - A Leader (But Emotionally Distant)
Best: Leadership--The man who never met a bow tie he didn't like had been helming the ship his adult life and once he stepped into any given situation, his was the only opinion that mattered. When the agency went into crisis mode after Roger's first heart attack, it was Bert (Robert Morse) who called the shots with the others doing his bidding.
Worst: Emotionally distant--The agency's founding partner and avid nipponophile could be a bit cold, such as the time Don refused to sign his contract, Bert, without a hint of avuncular concern, handed him the document with a pen, and said, "Sign it."
9 Sally Draper - Intuitive (But Melancholic)
Best: Intuitive--Before our eyes, Sally (Kiernan Shipka) went from 8 to 18, from tiny ballerina to boarding school brat to second mother to her younger brothers, Bobby and Gene. At every stage, Don and Betty's eldest understood the dynamic in her household but chose to suppress her feelings until she couldn't anymore.
Worst: Melancholy--There's a sadness about Sally for what might have been if her parents actually acted like decent human beings once in a while, so she often looks melancholic and acts out accordingly.
8 Harry Crane - Smart (But Self-Pitying)
Best: Self-preservation--"Crane" (Rich Sommer) as he was referenced, was an unimpressive account man who backdoored his way into becoming the head of the TV department (a job he created for himself before anyone realized there were big bucks in placing ads on TV shows), then parlayed that into wheeling and dealing in Hollywood.
Worst: Self-pity--"Everybody else gets (fill in a complaint here: a nice office, a raise, a partnership, a work trip to California...)." Harry never stopped to think maybe it was because they earned it while he was complaining.
7 Megan Calvet Draper - Kind-Hearted (But Manipulative)
Best: Kind-hearted--"Another girl used to have this job, and now she has everything," Joan said of Megan (Jessica Paré) who went from receptionist to Don's wife after, in the role of babysitter, she accompanied him and his children on a work vacation and, unlike Betty, displayed a lovingness towards Sally, Bobby, and Gene.
Worst: Manipulative--She was a failed actress who took a support staff job, married the boss who decided she had a knack for copywriting--a job traditionally done by men and Peggy Olson. When the agency sells a Cinderella-themed Butler Shoes campaign, Megan begs Don to play the starring role which signals that Showbusiness may be more important to her than her personal relationships.
6 Pete Campbell - Ambitious (But Underhanded)
Best: Ambitious--Pete (Vincent Kartheiser) was an over-achieving, up-and-coming account executive with big ideas, a prestigious Manhattan pedigree (his mother was a Dykeman), and a well-to-do fiancé who had a life/career plan that kept getting derailed by others, such as Bob Berenson (James Wolk).
Worst: Underhanded--So desperate because he wasn't moving ahead at the speed with which he believed he deserved, Pete snooped through Don's mail, threatened to expose his true identity, got Freddie fired, and pressed Joan to compromise herself to land the Jaguar account.
5 Joan Holloway Harris - Proud (But Desperate)
Best: Proud--She was the office manager who walked around like she owned the place. Joan (Christina Hendricks) always had her head held high despite that she was a mistress, not a wife, that Paul Kinsey (Michael Gladis) displayed her age via her driver's license to the whole agency, and her doctor husband chose Vietnam over her and their baby.
Worst: Desperate--The struggle was real for the single mother who grew tired of sashaying around the agency lording what little power she had over the secretaries. She went behind Pete's back to land Avon to become an account executive, then compromised on her own morals for a partnership.
4 Roger Sterling - Charming (But Lazy)
Best: Charming--Roger (John Slattery) was a wealthy scion who inherited his father's business. Client entertainment was his specialty. He could suck up with the best of them, and throw money around (especially at problems) to keep everyone happy and the environment upbeat.
Worst: Lazy--His name on the door was contribution enough. Aside from making phone calls and taking clients for drinks, any real work became the burden of subordinates, mostly Pete. He carried a wad of cash in his pocket so he could pay off people like Peggy, who he needed to fulfill an assignment he hadn't bothered to do.
3 Betty Draper Francis - Gracious (But Bitter)
Best: Gracious--"Bettes," (January Jones) as her ex-husband referred to her up until the end, was a former model living the traditional, happily ever after suburban life of a '50s wife. "Are you too sold separately," she and Don were asked, referencing the fact that the couple looked like Barbie and Ken. The Bryn Mawr grad was the perfect hostess and dinner companion when her husband needed to take clients out.
Worst: Bitter--It was only a matter of time before Betty realized she'd been sold a bill of goods. Her husband was a cheater, Ossining was isolating, and her children were a burden to care for. She remains miserable even after she finds a new husband, because of her jealousy over Don dating younger women like blonde Bethany Van Nuys (Anna Camp), and eventually marrying Megan.
2 Peggy Olsen - Conscientious (But Dissatisfied)
Best: Conscientious--Peggy (Elisabeth Moss) was a first-wave feminist, who started as support staff then rose through the ranks to Copy Chief. Aside from manning Mr. Draper's desk, her comments on Belle Jolie got her noticed and more assignments came along with a promotion. She worked for everything she got, and never said no to an opportunity.
Worst: Dissatisfied--"That's what the money's for", screamed Don after once again she complained that she was not getting enough credit. In particular, she was not recognized as the idea person behind the Glo-Coat commercial for which Don won a Clio Award and that lack of recognition always ate away at her.
1 Don Draper - Compassionate (But Selfish)
Best: Compassionate--Don aka Dick Whitman (Jon Hamm), was a rich, successful man who knew what it was like to be desperate, so he felt for others like his step-brother Adam, to whom he gifted $5000 in order to start over, and Freddie, who he defended when co-workers were mocking his alcoholism, and a down-and-out member of a self-help group to whom he offered moral support. Lest we forget how he cared for the real Don Draper's wife, Anna.
Worst: Selfish--He wanted what he wanted when he wanted it. Don saw no reason why having a wife should keep him from dating, left his colleagues high and dry when he felt like taking off on an impromptu vacation, could go without seeing his children for indefinite amounts of time, and promised Megan they'd begin anew in Southern California, only to change his mind.
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