5. Sal Romano
4. Joan Holloway/Harris
On the surface, Joan is a sassy secretary that can hold her own with the men in her office while still exuding femininity. Underneath that, though, is a young woman torn between wanting family or a job, romance or marriage, wealth or happiness. What makes her fantastic is her high level of confidence and unmatched ability to know exactly how to act (and how everyone else should act) in every situation - something that all of the men in the ad agency depend on. Her gorgeous red hair and curvaceous Marilyn Monroe style make her a unique fashion icon unlike most women on TV today.
3. Anna Draper
Anna is such a unique character to the show. Most of the series takes place on the east coast, except for Anna, who lives in California. Everything from her nearly-hippie clothes to her sunny disposition screams Californian, a stark contrast to the dark and cynical lifestyle of Madison Avenue. She knows all about Don's past - for a long time she was the only character who knew his real name - and still loves him like a brother despite all of the things he's done. Anna is the one point of truth and consistency in Don's life, and her death changes him. She is only featured in four episodes but has a profound impact on Jon Hamm's character.
2. Sally Draper
You don't often see fully developed child characters on adult dramas, but Mad Men does an excellent job of integrating Don and Betty's oldest daughter into the storyline. Sally is a spitfire of a young girl, full of her father's ingenuity, passion, and forwardness, as well as her mother's stubbornness. She tries to deal with an absent father, a distanced mother, younger siblings, the death of her grandfather, and eventually her parents' divorce and subsequent remarriages. It's a lot for a girl just now turning 12. Over the course of the series she has stolen and smoked her mother's cigarettes, made cocktails, learned to drive, and gone to see the Beatles. Sally knows a lot more than she lets on, and young actress Kiernan Shipka plays the troubled child beautifully.
1. Peggy Olson
Peggy is hands-down my favorite character of the entire series. If I had to choose someone from the cast that I identify with the most, it would probably be her. She's the only woman in the creative department, working hard to promote herself out of the pool of secretaries and into the world of mock-ups, pitches, and ad campaigns. She earns the respect of a lot of the men she works with, especially Don, who urges her to do better and even takes her with him when he leaves to form SCDP. She's pretty, but not a bombshell like Joan or a beauty like Megan; she often dressed frumpy and led a fairly conservative lifestyle (before the whole "secretly have Pete's illegitimate child and give it up for adoption" thing, at least). She's unlike most of the women portrayed in the show, as she values her career over marriage and housewifery, and is a lot more like leading man Don Draper than probably either of them want to admit. Despite the fact that Don's new wife Megan works at SCDP (and in creative under Peggy, no less), his "work spouse" is most definitely Peggy. Now that she's broken into the men's world of advertising she has been known to hang out with beatniks, smoke pot, and go to strip clubs with her clients. All the while rocking a Jackie-O hat like no one else on the series can.