‘Mad Men’ Season Five’s Most Depressing Moments

We've seen Don Draper do some pretty despicable things before – commit adultery, steal a dead man's identity, etc. But he never struck us as the murderous type. After a chance encounter with a former flame, Andrea Rhodes, an under-the-weather Don endures a fitful night of delirium. He has sweaty, passionate sex with Andrea, only to kill her as punishment for luring him to cheat on his new wife, Megan. It may not have happened in reality, but it was still plenty upsetting to watch Don strangle a helpless woman to death, even if she was just serving as a metaphor for his previously unfaithful nature.

You’d think Sally Draper would be grinning from ear-to-ear whenever her mom and stepfather go out of town. Not when Grandma Pauline is the babysitter. Henry Francis' mother is such a nightmare that Sally begs to stay with her aloof father, to no avail. Pauline winds up scaring Sally so shitless with her twisted version of the Richard Speck student-nurse-murder story (she paints the nurses as the ones responsible, as they enticed Speck) that the only way to get the girl to relax is to offer her a sleeping pill. Sally passed out cold under the couch is an extremely difficult vision to forget.

Throughout the season, Don and Megan's marriage has been a portrait of marital bliss – with the occasional vitriolic argument. The first one, in the season premiere, culminated in a round of steamy, dominatrix-tinged intercourse. But this one was way more disturbing, as Don came frighteningly close to physically hurting Megan. He had been worried sick over her disappearance (incited by Don's brief abandonment of her at the upstate HoJo's), so what does he do? Chases her around the apartment like a lunatic. When they both crumple on the floor in defeat, Megan makes this poignant observation: "Every time we fight, it just diminishes this a little bit."

Between Roger Sterling's continued infidelities with Joan Harris last season and his endless sniping with his wife, Jane, this season ("Why don't you sing like that?" "Why don't you look like [Don]?"), the demise of the second Sterling marriage was hardly a surprise. Still, it was no less sad to watch Roger and his trophy wife reach clarity about their dead-in-the-water relationship while under the influence of LSD, despite the matching hot-pink towel turbans. Their disconnect was sublimely illustrated by their inability to even share hallucinations together. Roger could see the 1919 World Series from their bathtub, but Jane couldn't.

New staff copywriter Michael Ginsberg gave Don a run for his money as the most enigmatic character in the Mad Men universe for several episodes, until he dropped this bombshell during a late-night work spree. Up to this point, Michael was just a preternaturally talented ad man with zero social graces and a penchant for plaid jackets. But this glimpse into his past helps to explain why he seems so damaged – and why he's hostile toward his "father," Morris, who adopted Michael when he was five. His only family history is that his mother died at the hands of the Nazis.

A live-in sex partner or a cat? Which would you choose? If it were up to Peggy Olson's Catholic mother, Katherine, it would be the latter. After Peggy announces that she and her political journalist boyfriend, Abe Drexler, are planning to move in together, Katherine berates her daughter for "selling herself short." But the underlying issue that emerges from this conversation is the fact that traditionalist Peggy, who initially wished Abe had proposed, is willing to risk "living in sin" because it means she won't be alone. It's not like the alternative her mother offers is any better: "If you're lonely, get a cat."

The theme for Sally this season is without a doubt "I'm Not a Girl, Not Yet a Woman" – culminating in the arrival of her first period in the penultimate episode. Wherever she turns, she's met with another facet of the seedy underbelly of adulthood, whether it's student-nurse murders or learning her father had another wife before Betty or Megan. But nothing could have prepared her for the sight of her step-grandmother with a mouth full of Roger Sterling. Kiernan Shipka superbly conveyed Sally's revulsion, not just in her facial expression, but when she summed up New York in one word to Glen Bishop: "dirty."

Pete Campbell's personal life has started to mirror that of a pre-Megan Don, with Pete ditching Trudy for the company of women like Beth Dawes, the wife of his (also-cheating) commuting buddy. Pete becomes obsessed with Beth after their one-time tryst, and even though she voices a desire to keep their affair going, she refuses to follow through, escalating Pete’s despondency. One night, Beth is about to drive home with her husband from the train station, but not before sending Pete a message via her fogged-up car window – a heart – that is quickly erased when she rolls down the window.

There have been only a couple of fleeting moments in which Betty Francis has aroused our sympathy this season, and this brief whipped-cream binge is one of them. She's just come home from an awkward run-in with her ex-husband's young, slim new wife, Megan, at the Drapers' swanky Manhattan high-rise, and she's feeling pretty self-conscious about her weight gain. So she seeks comfort in a can of Reddi-Wip – no cake or ice cream necessary. But immediately after putting tube to mouth, she remembers her diet (remember that paltry one Brussels sprout for Thanksgiving dinner?) and hacks the creamy goodness into the sink.

Harry Crane's unhappy marriage is hardly a secret. Why else would he procrastinate going home by eating an entire sack of White Castle? We've seen him be unfaithful before, but his sexcapade with Lakshmi, the object of infatuation of his former colleague and Krishna convert, Paul Kinsey, brought his infidelity to a new level of odiousness. And it wasn't because she wanted to take it up the ass. Following their hookup, Lakshmi's cray-cray colors emerge: She orders Harry to end his rekindled friendship with Paul – driving her point home with a slap across his face – lest the Krishna movement lose their best recruiter.

In one of Mad Men's more controversial episodes, a representative for potential client Jaguar requests one night in heaven with Joan in exchange for a guarantee that SCDP will land the sports-car account. Don, disgusted that the offer was even presented to his longtime colleague – who ultimately agrees to the deal for the price of a partnership – goes to Joan's apartment the night before the Jaguar pitch in an attempt to stop her from degrading herself for the sake of the company. The way Joan's eyes fall signals that Don is too late – she's already done the deed.

There's only so much lack of appreciation a person can take, and even Peggy Olson has a breaking point. After being overlooked yet again in favor of talented new kid Michael Ginsberg, the SCDP copywriter gives herself an upgrade – in the form of a copy chief position at rival firm CGC. Don takes her decision as a personal affront, and tells her not to bother giving two weeks' notice. But when she extends her hand to say good-bye, fighting back tears, Don realizes he's lost his best collaborator. He presses his lips to her knuckles and lingers there for several seconds, unwilling to let her go.

The British financial officer had been showing signs of money trouble as early as the season premiere, but it wasn't until later episodes that we learned how dire his situation had become. When Don finds out that Lane had embezzled funds from SCDP to pay back taxes (and forged Don's signature on the check), he has no choice but to demand his resignation. Personally and professionally humiliated, Lane takes his own life by hanging himself on the door to his office – following a botched attempt to asphyxiate himself in his brand-new Jaguar – leaving his colleagues to discover his dead body.

We’ve watched Pete do some despicable things this season, not the least of which was to spearhead Joan’s effective prostitution to land the Jaguar account. But he still managed to arouse our sympathy when his doomed infatuation with Beth Dawes came to a heart-wrenching conclusion. Beth has been battling depression, and her choice of treatment is electro-shock therapy. Following her most recent round of EST, Pete visits her in the hospital, only to find she no longer recognizes him (or does she?). Still he pours out his soul to Beth, revealing that his love for her made him realize that his life with his family was a "temporary bandage on a permanent wound."