17. Sally Draper, as seen on Mad Men, portrayed by Kiernan Shipka
In the beginning, so fascinated by Joan Holloway and Peggy Olson (2 amazing female characters as well), I missed Sally's awesomeness. But when Grandpa Gene came to stay with the Drapers, so did Sally's overwhelming greatness, so this entry might not be as coherent as some.
Sally is the oldest child and only daughter of Don and Betty Draper. She's pretty but not pretty enough for her mother; for Betty, who is the very definition of a proper lady, Sally, who is so much like her father, is frustrating and confusing. Sally sees her mother's beauty but she doesn't feel any true kinship with her; Sally's love has always firmly belonged to Don, who, for all of his faults, is a surprising good parent when he puts the effort into it. From Grandpa Gene's death to her parents' divorce (her plaintive cry to Don that he promised he'd always come back is particularly heartbreaking) to her friendship-on-the-brink-of-more with Creepy Glen, Sally's narrative is very much about growing up when the adults around you aren't doing a great job as adults and having to find your own way.
Seasons 4 and 5 are particular high points for Sally. Sally and her sexuality have started to come into play, which is a bold move, I think, for a girl who is still just on the brink of puberty. Last season, Sally gets caught masturbating at a friend's sleepover, and Betty reacts exactly the way you'd think Betty would react, telling her that it is something only fast, "bad" girls do (which, given that I highly doubt Betty knows where her vagina is located, is likely something her own mother told her.) We saw a particularly funny conversation between Sally and Joan about breasts ("You have big ones. My mom has big ones. I'm going to have big ones one day.") And, just this past week, we saw Sally's development brought to Don's attention. As she comes out for the American Cancer Society dinner in her mod dress and boots, hair and make-up done, we see Don pause, almost amazed, that his little girl looks so grown-up (which is why he tells her to lose the boots and makeup.) Dr. Calvet's pointed line about how, "Every little girl will eventually spread her legs and fly away" underscores that Sally isn't just growing up quicker than Don would like (nothing like catching your father's buddy being fellated by your stepgrandmother!) but is also coming of age in the late-60s, which wasn't exactly the most demure of times.
But what I love the most about Sally is, at the end of the day, when she's done driving her mother crazy and begging her father to please rescue her from her mother's new family, she's painfully real. 1960s or not, Sally Draper is essentially a child of divorce who has to grow up too fast, and it's the single most relatable thing about her. She resents her mother, she idealizes her father, she's fascinated by her hip stepmom, she tries to wrangle her brothers so they don't get them sent back to their mom's house; Sally is just trying to find her way in the world like every other character on the show and often times she does a better job of it than the adults.
Which, for a girl who isn't even in junior high, is pretty kick-ass.