First of all, Mad Men is not (and is not intended to be) a realistic portrayal of the 'Sixties. Rather, it is a kind of satire of the nostalgia of the dark underbelly of the period of post-war, baby boom prosperity, kind of The Man in the Gray Flannel Suit if it were directed by Douglas Sirk or Billy Wilder.
The character of Don Draper (the ‘fake’ Draper) is an allegorical representation of the conflict between superficial Victorian-esque, Wonder-Bread-and-mayonnaise values that the culture of the United States returned to in the 'Fifties versus the new-found sexual freedom and liberation of the 'Sixties. To speak of Don being ‘good’ or ‘bad’ is missing the point; Don really has no values of his own, no heritage to build upon, and even within the show he is a fiction of a man, an image of success and vitality which is strictly an artifact of his own creation. Draper is whatever he has to be to fit into the situation; his ability to become the ubermensch in any situation is also his failing, in that he is a default leader, followed by others, but doesn’t have a clue as to where he is going next.
Like the advertising campaigns he so carefully crafts, he is all front and back but hollow in between, filled in with consumer products (apparently mostly cigarettes and Old Fashioneds), meanwhile trying to find some kind of fulfillment in what he believes (or at least has sold himself on) to be the perfect lifestyle; a house in the 'burbs, the beautiful blonde ex-model wife, the 2.3 kids, and dog. (Note that after a day of drunken frustration at trying to put together a playhouse and disappearing after picking up the cake, he actually returns with a Golden Retriever, creating the perfect picture of suburban life even as he acts like a “complete heel.”)
However, this life isn’t any more satisfying than being Dick Whitman, so he embarks on yet another life, one of debauched hedonism with women who would be socially unacceptable for him to marry (a bohemian artist, a Jewish department store owner, a comedy promoter from low class upbringing). It is interesting it is this life that we see first, and it seems an appealing one, devoid of obligation and responsibility, but ultimately Don is drawn to and honors, if in erratic fashion, the commitments he is subject to (supporting the real Don Draper’s wife, providing financially for his half-brother, protecting the knowledge of Peggy’s pregnancy and abandoned baby), but at the same time, fails in many of the responsibilities of his marriage, fatherhood, and even on occasion his job.
He is, in other words, an avatar of the American culture of his time; embracing social liberalism and responsibility on one hand, but at the same time repressed by his past shame and lack of true identity, seeking to escape to a new frontier, not that of Horace Greeley’s “Go West, young man,” but of publicity and technology capable of manipulating the social fabric. He’s not supposed to be likable, or even really understandable as a person.
Other major characters can be seen in similar vein. Personally, the character I find most intriguing is Joan Holloway (notwithstanding that she looks like a real world incarnation of Jessica Rabbit), and I hope they develop her further.
Stranger