By Adam B. Vary
June 10, 2012 at 10:57 PM EDT
Michael Yarish/AMC
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I have friends who’ve proclaimed the fifth season of Mad Men to be the show’s best yet. I have colleagues (both at EW and elsewhere) who’ve felt the season started with some of the show’s strongest episodes ever (“Signal 30,” “Far Away Places”), only to drift into grey angst, needless tragedy, and too-obvious thematic unity in its final episodes. And I’ve read many comments on our recap message boards that have expressed in quite colorful terms that this entire season has been ruined by the singular presence of Don Draper’s new wife, the well-adjusted, self-assured (or gap-toothed and petulant, depending on your point of view) Megan. (As you may have surmised, this post will be looking back on the entire season thus far, so consider this a SPOILER ALERT for all those who have yet to catch up.)

Me? I’m reserving judgment until after tonight’s finale. If Mad Men has taught me anything this season, it’s that a single episode can force me to re-think every episode that has come before it — and then the subsequent episode will send me down that rabbit hole all over again. So while I’m still reeling from Lane’s suicide, Peggy’s exit, Joan’s professional harlotry, and Don’s complicated relationship with each of these pivotal events, I await tonight’s season finale with a feverish foreboding, wondering how it will recalibrate my thinking once again.

With all that nonsense bouncing around my head, I thought it would be good to assess the journeys of Mad Men‘s key characters this season, and share my hopes and fears as to what is in store for them tonight. Here are my thoughts:

DON DRAPER

He started the season on “love leave,” so focused on his own happiness with Megan — on not being “that guy” anymore, literally choking off his urges to stray — that he failed to look after his job and, in turn, his wife’s happiness with her job. But once Megan left SDCP, without her constant presence warding off Don’s demons, he began realizing just how old he’d suddenly become. The world was rapidly changing, what was cool and hip no longer made sense, and his once magic ability to conjure cutting-edge campaigns had dulled from underuse. After a night of flirtation with Joan — flirtation with her, and with his darker instincts — Don redoubled his efforts on the job, fighting for and winning a coveted campaign for Jaguar cars. But that wasn’t enough. The struggle had meant Joan had to compromise herself, and Don’s neglect had pushed Peggy away — all that loss, and the reward was a car that never worked?

So Don went after Dow, a behemoth of American industry, and his pitch said as much about himself as the company he was trying to win over: “What is happiness? It’s a moment before you need more happiness. I won’t settle for 50 percent of anything. I want 100 percent. You’re happy with your agency? You’re not happy with anything. You don’t want most of it. You want all of it.” The pitch was a grand slam — and then Don came back to the office to learn that Lane had hung himself in the office just days after Don had demanded his resignation for embezzling funds from the company.

Hope for tonight’s season finale: Don hadn’t told a soul about Lane’s misdeeds, though Bert Cooper was at least wise to a check Lane cashed for $7,500. I hope he comes clean, and begins to find a balance between major achievement and lasting personal happiness.

Fear for tonight’s season finale: Don has never been one for self-disclosure nor lasting happiness. But I’m more concerned that with all this loss, he’s going to cling that much more tightly to Megan — and, in doing so, drive her away. And as we saw from season 4, Don does not do being alone all that well.

PEGGY OLSON

While on a personal level, Peggy took the very big (and very modern) step of having her boyfriend Abe move in with her, she spent all of season 5 in a frustrating state of professional limbo. Her pitches to Heinz Baked Beans flopped so badly with the clients that she was taken off the account. Her latest hire, possible Martian and definite oddball Michael Ginsberg (Ben Feldman), eclipsed her output of top-notch campaigns. Don barely paid any attention to her all season, and when he did, it wasn’t exactly supportive: After she noted she should be able to see through her Parisian pitch for Chevalier Blanc cologne, Don literally threw a wad of cash in her face. So Peggy quit, joining SDCP arch rival Cutler Gleason and Chaough.

Hope for tonight: Not a word about Peggy was mentioned in last week’s episode, but I hope at the very least Peggy will show up for Lane’s funeral (if we see it).

Fear for tonight: Peggy doesn’t show up at all once again, and we’re left to wonder whether she has any kind of lasting future on Mad Men.

PETE CAMPBELL

With his wife forcing him to move out to the Connecticut suburbs for the good of their child, Pete fell into to a selfishness that was breathtaking even for him: He kneecapped Roger with the Mohawk Airlines account; he flirted with an affair with a teenage driving classmate; he slept with a prostitute, then with the unhappy wife of the horndog commuting “buddy”; and he engineered Joan’s evening with the Jaguar executive. Like Don, Pete was not satisfied with all the great things he had in front of him; unlike Don, he had no moral compunctions about seeking out more satisfaction no matter who else would get hurt in the process. At least we got the satisfaction of seeing Lane knock Pete flat on his fanny.

Hope for tonight: Pete attempts a power play after Lane’s departure, and Roger knocks him flat on his fanny.

Fear for tonight: Pete attempts a power play after Lane’s departure, and succeeds.

NEXT PAGE: Joan, Roger, Betty, Sally, Megan, and the rest of the gang

JOAN HARRIS

It did not take long after Greg’s (brief) return home from Vietnam for Joan to kick her rapist husband to the curb, but the decision left her in a most precarious position as a single mother in 1966. Yes, Joan’s mom Gail was around to help out, but the price was her constant passive-aggressive disapproval. Joan was too proud to accept help from Roger, because she knew all too well how emotionally unreliable the real father of her child could be. But with the pressures of single motherhood mounting, Joan allowed herself to be pimped out by Pete Campbell in exchange for a five percent stake in the company and a voting partnership in the firm. It was a decision I suspect will remain hotly debated well beyond the run of the show, but it left Joan in a place of real power she’d never experienced before.

Hope for tonight: I’m going to steal a prediction from an astute commenter from last week’s recap: Lane bequeathed his stake in SCDP to Joan, leaving her with more shares in the company than any of the other partners. SCDP becomes SCDH.

Fear for tonight: Ken’s offhand comment last week that he knows what’s entailed in being a partner had the devastating side-effect of suggesting that he knows how Joan became one. If Ken knows, everyone knows, and Joan’s going to realize that she’s never going to live it down.

ROGER STERLING

After starting the season feeling more useless than ever, Roger let his wife Jane convince him to drop acid — who knew that LSD would be like spinach to Roger’s Popeye? With a youthful spring in his step, Roger left Jane and, like Don, redoubled his efforts at work. Unlike Don, Roger also let himself dive deep into his old bad habits. By the end of the season, Roger’s “enlightenment” had faded — and the giant money roll in his pocket was much lighter.

Hope for tonight: Roger rallies the firm in the wake of Lane’s death to land Dow and lift Don’s spirits.

Fear for tonight: Roger takes Lane’s death much harder than he lets on, foreshadowing a darkening spiral for his character in the season to come.

BETTY FRANCIS and SALLY DRAPER

Thanks to January Jones’ pregnancy, the newly zaftig Betty Francis was often M.I.A. this season, and her arc was barely developed: A cancer scare drove Betty to Weight Watchers, but she still was perfectly fine trying to use her daughter Sally to force a wedge between Don and Megan (unsuccessfully, as it turned out). Sally, meanwhile, was chafing under the gothic oddness of her new life under Henry Francis’ roof (and Mama Francis’ thumb), leading her to reach out even more to quasi-boyfriend Glen and making her something of a snotty brat. She also faced two major milestones of adulthood: Witnessing her first sex act (Megan’s mother giving Roger a blow-job), and having her first period (while on a date to the Natural History Museum with Glen). Fascinatingly, the latter event fostered an unexpected bond between Sally and Betty.

Hope for tonight: Betty’s maternal instincts snap into focus, and she guides Sally into a shockingly well-adjusted adolescence.

Fear for tonight: Betty picks a fight with Henry, and then Megan, while Sally raids the liquor cabinet and loses her virginity to Glen. [Shudder]

MEGAN DRAPER

Bringing a stability and honesty to Don’s life that he’d never experienced before, Megan was also unafraid to stand up for her own happiness. This meant leaving SCDP just as she was becoming its star employee to pursue a career in acting, and throwing a fit whenever Don behaved like a jerk. Her clear-eyed aim is to avoid all the mistakes of her parents’ deeply unhappy marriage, but her age difference with her husband also leads to confrontations with Don that probably could have been avoided.

Hope for tonight: She lands a big play in New York, and Don is able to celebrate it with her.

Fear for tonight: She lands a smallish role in Los Angeles, and Don tells her she can’t go.

KEN COSGROVE, HARRY CRANE, STAN RIZZO, and MICHAEL GINSBERG

The moody dissatisfaction hovering over the lives over the main characters on Mad Men this season trickled down into the lives of its featured players: Ken pursued a secret career as a pseudonymous novelist; Harry boinked his old best friend Paul Kinsey’s girlfriend in his office; Stan grumbled about never feeling satisfied with his work; and Ginsberg threw a fit when Don declined to pitch his (better) idea.

Hope for tonight: Nobody is a jerk to Joan, everyone works together to land Dow, and Kenny leaves the firm to join Peggy at CGC.

Fear for tonight: Everyone’s a jerk to Joan, and Harry is promoted into Lane’s job.

Your turn! How have you felt about this season of Mad Men? And what are your biggest hopes and fears for the season finale?

Follow @adambvary

Read more:

Jared Harris talks about last night’s shocking ‘Mad Men’

‘Mad Men’ and Peggy Olson: Where does she go from here?

‘Mad Men’ review: Losing enlightenment as the show heads to its season finale

Jon Hamm stars as Don Draper in the Emmy-winning ’60s-set drama
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