Mad Men/Tear Jerker

In the Season One finale of Mad Men, Don Draper manages to do this with a sales pitch for his slide projector advertising campaign: words cannot quite do this scene justice. And, because this show delights in trampling on its viewers' hearts, we cut to him getting off the train, to him coming home to his joyously happy family for Thanksgiving... and then to him getting off the train again... yep. Turns out the last scene was a fantasy, they have gone away for the holiday without him, and he's left sitting alone on the stairs in the dark. With "Don't Think Twice, It's All Right" playing on the soundtrack.
Peggy's flashback, in an episode where people have constantly been trying to get her to explain why she's so loyal to Don, to his visiting her in the hospital after the birth of her illegitimate son: she's drugged half out of her mind, near-comatose with depression, and unable to so much as speak to anyone or admit what happened:

Don: Why are you here?
Peggy: I don't know.
Don: What do they want you to do?
Peggy: I don't know.
Don: Yes, you do. Do it. Do whatever they say. Peggy, listen to me: get out of here and move forward. This never happened. It will shock you, how much it never happened.

- Becomes Harsher in Hindsight after The Fog, where we see what it was like for a woman to give birth in the early 1960s. Betty was on her third child, at her chosen hospital, had her husband present at the hospital to support her, and yet the whole experience came across like a Lynchian nightmare. Twilight Sleep was Nightmare Fuel for even those who had gone through a pregnancy before. For poor Peggy, who probably had little to no knowledge about her body and sexuality, much less SOP for a woman in labor, the whole experience must have been that much more nightmarish.
Don's wife Betty gets a half-an-episode-long one in a later episode, when she's struggling to deal with her suspicion that Don is cheating on her again. After she tears the house apart looking for evidence, any evidence, and can't find any, Don comes home to find her sitting on their bed, beyond numb, in full-on BSOD mode (and a total disheveled wreck, still wearing last night's bright-colored party dress, in contrast to her normal fanatic perfection), with all his clothes pulled down from the hangers and the shards of a broken wine glass on the floor. Her only words to him are "I would never do this to you."
One feels pity for Duck Phillips when he learns that his ex-wife is getting remarried and that his children really don't need him anymore. Luckily he gets his beloved dog Chauncey back. No wait, he locks Chauncey outside of the Sterling Cooper building and walks away, leaving the poor dog to fend for itself on the streets of New York City.
Joan telling Peggy that she's marrying her fiance at Christmas, just before Peggy closes her brand new office door. Doesn't seem like a tearjerker until you consider that Joan's fiance just raped her on her boss's floor and she has to act like nothing happened and that she's still thrilled to marry her "doctor."
Joan breaking down and crying in public at her going-away party, after finding out that her husband -- yes, she married him, tearjerker in and of itself -- didn't get the position they'd been counting on, that they therefore desperately need the income she's losing by leaving her job, and that everything she's spent her life working for is going distinctly to hell.
Sal, when he realizes that Don is not going to save him from being fired due to resisting Lee Garner Jr.'s sexual harassment. Even worse was Don's slur of "you people"--not only was Don not coming to the rescue, but he was part of the lynch mob.
Don telling Betty about his brother's suicide.
"Somebody very important to me died."
This show's re-creation of the national mood of when JFK was assassinated.

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