With the show’s fourth season coming to an end Sunday, we're still only inching toward the very complicated answer. But the journey into the meaning of identity has proved, at times, riveting.
This will go down in “Mad Men” annals as the year we saw Draper, the buttoned up 1960s ad man with a hidden past, finally lose control and weep at the loss of the only woman who understood him – and the only one, seemingly, he never tried to bed.
While it feels as if the last dozen episodes have flown by, the pace of the story has slowed – which isn’t necessarily a bad thing.
Season 3, still probably the best yet, was driven largely by external forces, with the Kennedy assassination upending the characters' unexamined lives. The latest crop of shows has been more about internal struggles and searches for a sense of self.
We've seen the image-obsessed Draper make stabs at introspection, cutting down a tad on his prodigious drinking and starting a (somewhat lame) diary. It's notable that after his emotional breakdown he sought comfort in the arms of the comely shrink he initially scorned for her research into consumer psychology.
Perhaps the season’s most compelling storyline – and best performance – has centered around Don's grade-school daughter Sally, a little girl lost between her absent father and a cold mother more childlike than her in some respects.
Sally, who has run away from home and trafficked in other mischief amid her parents’ divorce, seems to have traveled the furthest of any character toward maturity, thanks largely to sessions with a child psychologist. But her emotional wellbeing remains precarious.
Gravity-defying office manager Joan Holloway appears to have finally started to assuming control of her shallow life, perhaps taking the face-flop office death of crotchety lifetime secretary Miss Blankenship as a wake-up call – even if viewers saw it as a hilarious, dark comic moment. Boozy, screw-up ad firm partner Roger Sterling dictated his gussied-up memoirs into a tape recorder, edging him to the sad middle-aged realization that his treating life as a joke has turned him into one.
Meanwhile, Peggy Olson, the ambitious copywriter with a secret of her own, is showing signs of becoming much more than Draper’s shadow and his disciple in denial, as she’s drawn to a bohemian crowd and starts to question her career.
It's no simple task to take characters' interior conflicts and turn them into gripping viewing. But show creator Matthew Weiner learned well from his time on "The Sopranos." While Tony Soprano often was smack in the middle of blood-soaked action, the sad and violent heart of the story played out primarily in Dr. Melfi's psychiatric office – and, sometimes, in actor James Gandolfini’s eyes.
There's plenty of turmoil surrounding Draper – most significantly the uncertain future of his ad firm. The title of Sunday’s finale, “Tomorrowland” – an apparent nod to the Disneyesque from a show that’s anything but – suggests that more big changes are coming.
But it's been the characters’ inner stories, conveyed through fine writing and performances, that's propelled another fine season.
"The Sopranos" sputtered a bit in its last couple of years, and wheezed to an end. But we're expecting a lot more from "Mad Men" and Weiner, whose latest effort will keep us coming back for new pieces of the Don Draper puzzle.
Hester is founding director of the award-winning, multi-media NY City News Service at the City University of New York Graduate School of Journalism. He is the former City Editor of the New York Daily News, where he started as a reporter in 1992. Follow him on Twitter.