Assessing Mad Men's Strange, Ominous, and Revealing 6th Season

At some point, I'm going to have to start a tally on this blog for every time I reference season 5 of Mad Men, given how many times I've already mentioned it in just 35+ posts.  I only reference it constantly because it's such a towering work of art, one of my favorite seasons of television ever.  There's not a bad episode in the bunch, but the middle stretch of episodes in particular -- from "Signal 30" to "Lady Lazarus" -- are probably the best string of episodes I've seen since the last 9 episodes of The Sopranos.  After such an artful, auteur-driven season, anything after that was bound to be somewhat of a letdown.  Season 6 of Mad Men almost felt conscious of this fact, seemingly going down its own rabbit hole and becoming as weird as ever.

Not since The Sopranos (maybe I need to start another tally) have I seen such bizarre things seem so natural.  By the time the second or third strange plot point occurs, you just sort of roll with it, like "yeah, that happened."  In one season, we got: Peggy stabbing Abe with a makeshift spear, Bob Benson and his gay grifter friend, Ken Cosgrove getting shot in the face, and the entirety of "The Crash."  The reason all of it felt so natural is because of how much it was in tune with the season's goal of presenting this world as one that is slightly oblique.  Season 6's events took place in 1968, and it kind of paralleled the time period, which saw the nation witness a side of themselves that they'd never seen before.  So it was only fitting that Mad Men felt a little less Mad Men-y this year too.  There was so much violence and tragedy in the world that it couldn't help but make its presence known in the show.  Sirens and news reports of national unrest could be heard and seen in many scenes throughout the season, as if the background was slowly seeping into these usually sealed off lives.

The off-kilter nature of the season made it feel like a slight disappointment for a very long time, which was something I didn't know how to process coming from my favorite show on television.  It's not that I thought it was a bad season, I don't think I could ever truly dislike a season of Mad Men.  There were some superb individual moments and episodes, but to me it wasn't creating a satisfying whole.  Perhaps it was just a me problem and not the show's problem, but I found the thematic throughline of the season and a given episode much harder to suss out.  I loved "The Flood," "For Immediate Release," and "The Crash," but nothing completely bowled me over the way that other seasons were capable of doing.

It wasn't until near the end that things truly started to cohere.  As it turns out, the key to the puzzle of the season was, naturally, Don Draper.  At the beginning of the season, when it looked like we were going to get the same old infidelity story and we kept getting flashbacks to Don's youth (flashbacks have never been the show's strong suit), it seemed like Matt Weiner was just treading water with the character.  Much like on Weiner's old job at The Sopranos, he highlighted the fact that Don is not somebody we're supposed to root for.  He's a man who does what he wants, with little regard to others, just leaving destruction in his wake.  This all culminated in the penultimate episode, "The Quality of Mercy," where Peggy literally calls him a monster, giving voice to many of the audience's thoughts as we've watched him over the last few years.  It was then that everything with Don began to transform.  Don's been driving everyone away in his life, particularly the women closest to him: Peggy, Sally, Joan, and Megan.  All of the flashbacks about motherhood and prostitution take on more power in this light, and what initially seemed aimless and ham-fisted revealed itself to be informative in regard to Don's slow wilting.

So, aside from Don, what was the season about as a whole?  In the finale, Betty has a line when she's speaking to Don on the phone about Sally where she says "the good isn't beating out the bad," and even though it was specifically about Sally's behavior, it's fitting for a season that's all about personal wars being waged.  Some were internal, like Don vs. his past, and others were external, but there was a tug of war going on in every corner of Sterling Cooper & Partners.  From the merger between SCDP and CGC to Don and Megan's marriage, season 6 was all about sustaining that which cannot be sustained.  We know that both are doomed to crumble, or at least slightly fall apart, and every episode has an ominous inevitability that Mad Men excels at.  Another big element of the season was the idea of ownership over things that can't be owned.  Prostitution, which often makes the customer feel like they have complete ownership even when they don't, is brought up multiple times throughout the season, and it ties into many of the stories this year, like Don and Ted's battle for Peggy.  They both treat her like she's the concept that they want her to be and not the person that she actually is.

What intrigued me the most about this season was how it subverted our expectations of what television does, but taking common ideas and putting a little slant on them instead of just eschewing them completely.  "History repeats itself" is not exactly new territory, but when other shows or movies try to play with that theme, they always treat time as if its a circle, neatly looping back where it started.  Mad Men is the first show I've seen that really gets how time works, and season 6 wasn't just about how history repeats itself, but instead about how it often folds in on itself.  The season constantly played on the ideas of doubles and duality -- Bob Benson's false identity mirroring Don Draper's, Sterling and Cutler playing similar roles, a character named Margaret getting axed as soon as Peggy comes back -- but it wasn't neat and clean in its parallels.  Characters' pasts bled into their present, creating an inseparable mixture within them.

We're also trained to believe in the idea that "the truth will set you free," yet throughout the season we got examples of that not being the case.  When characters gave into their desires or admitted something about themselves, it usually turned out to cause trouble, like the romantic entanglements of Peggy and Ted.  Even if it was just momentarily, like everybody being mad at Joan when she tried to go after the Avon account by herself or when Pete found out that Bob was lying about his identity, the true sides of these characters often threatened to topple their carefully constructed fronts.  We see this most significantly in the finale, where Don Draper, a man who's kept his past so guarded behind walls of his own making, finally reveals the real nature of his upbringing during a Hershey pitch.  For once, he's trying to better himself -- quitting drinking, deciding not to run away to California, opening up about his past -- and what reward does he get?  He gets suspended from his job, Megan walks out on him, and though he's made some roads to connecting with his children, they're only baby steps closer to him than they were before.

I usually hate it when seasons completely structure themselves around the ending, but "In Care Of" really worked for me in the way that it snapped together all of the previously disparate pieces of season 6.  It was all about these pyrrhic victories, how we may feel like we've made progress but we're still not any further down the road.  I suspect now that I know what the season was trying to get at, I'd enjoy it much more on the rewatch.  Even at the end of this initial watch, I thought this was still one of the best things on TV this year, a strange season from a willfully contrarian show.  If anything, it served as a nice precursor to the end, an interlude bridging the gap between the restless 5th season and a hopefully staggering final run.