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Tear Jerker: The West Wing
Absolutely everything associated with the real life death of John Spencer (Leo):
"Election Day." Specifically, the end of part one and the opening moments of part two, especially the all-too-real reactions of the cast members as they finally got to acknowledge the death on-screen.
On that note, Martin Sheen's quietly dignified tribute before Spencer's final featured episode worked as well as any scripted tearjerker.
Similarly, when Lou tells Santos not to release a statement because it will allow Vinick to win and "when Leo wakes up, he will kick your ass for letting that happen." At this point the audience knows that Leo is already fated to die because Real Life Writes the Plot, and seeing the characters so sure that he'll be OK is heart-wrenching.
Near the end of "Two Cathedrals", the second season finale. During a tropical storm, the door leading from the Oval Office to the Rose Garden bursts open due to an issue with a faulty latch mentioned earlier in the episode. President Bartlet, having just returned from Mrs. Landingham's funeral, loses his temper and shouts for Mrs. Landingham out of habit. Moments later, she opens the door from the reception office and walks in, saying simply, "There's no need to shout". The two have a conversation, where Mrs. Landingham prods Bartlet into remembering all of the work and good deeds he can still accomplish. She finishes by saying, "If you don't want to run again, I respect that. But if it's because it's too hard or because you're scared, well then, God, Jed, I don't even want to know you" and walks out the door, closing the door behind her.
The fact that the phrase echoes one that Mrs. Landingham used to get Jed involved in a just cause when he was very young added more poignancy to the scene.
I think everything she said in that scene she said before she died and Bartlet remembered it. He cared enough about so many things she said from so long ago to remember them all this time. That's a tear jerker right there.
No, that can't be right, because he asked her to come back to the White House so he could tell her about the MS- the accident was on her way back.
Topped at the end of "Bartlet for America" the next season, as we find out exactly what Leo went through to get Jed to run in the first place. The final line, "That was awfully nice of you," provokes bawling in almost everyone.
The look on Donna's face when the others tell her that Josh has been shot and might not make it.
Worse for this troper was everyone else's faces when she came in all anxious and relieved to hear that the President was okay: a lot of frozen expressions, all glancing back and forth, nobody wanting to be the one that says it. Of course, that was probably not helped by having had to deliver bad news shortly before watching it.
Other heartbreaking moments for her include a shot of her and Mrs Landingham sitting together and holding hands, and later going up to the observation desk to watch Josh's surgery.
Also When Josh wakes up and asks "What's next?" at the beginning of season 2.
Not to mention the 3rd season finale with the death of Secret Service agent Donovan, just as he and C.J. were growing closer, done to "Hallelujah".
The end of "20 Hours in America", with one of the most heartbreaking speeches in the series (about a school bombing where many people were killed), set to Tori Amos' cover of "I Don't Like Mondays"
And the end of "In Excelsis Deo", where Toby sets up a funeral for a homeless Korea vet and Mrs. Landingham, who lost her two sons in Vietnam comes along. And the rest of the cast listen to a boy's choir sing "The Little Drummer Boy".
Bartlett: If we start pulling strings like this, you don't think every homeless veteran will come out of the woodwork?
Toby: I can only hope, sir.
And earlier in the episode, the conversation that Mrs. Landingham has with Charlie, where she explains that her sons were killed near Christmas and how she imagines what it must have been like for them to die in a war so far from home, and wishes that she could have been there to comfort them.
"I miss my boys."
The whole of Toby's quest to find out who the homeless man was is a slow, painful build-up of just how badly America failed its veterans—the emergency officials in the beginning who treated the death as of little importance, for instance, and when Toby finds the man's brother Walter living under the bridge and has to give him the news. He tries to say that he can arrange a funeral because he is a powerful man, but under the bridge his words his power is useless and he knows it.
Andy telling Toby why she won't remarry him, and likely why they divorced in the first place.
Andy: You're too sad, Toby. You bring the sadness home with you. You're just too SAD.
Toby: Did you feel that way when we were married? That I was SAD? Did my [voice breaks] friends feel like that?
"Noel". All of "Noel", but especially Josh screaming at Bartlet in the Oval Office about the "sirens" and Leo's "man in a hole" speech.
The part that always gets me comes towards the end of Noel, when Stanley tells Josh his diagnosis.
Stanley: You have Post Traumatic Stress Disorder.
Josh: Well... that doesn't really sound like something they let you have if you work for the president.
Josh: Can we have it be something else??
Leo's "guy in the hole" speech in Noel gets a beautiful Call Back at the start of the aforementioned Bartlet for America.
Josh: I'm gonna help you out, you know why?
Leo: Because you're so obsessed with everyone you love dying that you're a compulsive fixer?
Josh: [smiles] No, Leo, it's because a guy's walking down the street and he falls in a hole, see.
The moment in "Twenty-Five" when Abbey is briefly determined to go into the press room to make a direct appeal to the people who have kidnapped Zoey, because she'd "seen other mothers do it".
Whatever people may say about season five, the last sequence of "7A WF 83429", which cuts together scenes of the Bartlets and Charlie attending a private mass, Josh and Donna leaving the White House to see hundreds of tributes to Zoey, and the search for her continuing in the situation room, and is set to Lisa Gerrard's song "Sanvean", is heartbreaking for all the right reasons.
The scene in the final episode, where current Chief of Staff CJ gives the traditional note to her incoming counterpart, Josh. It simply says "WWLD?": What Would Leo Do?
The episode "Gaza". The entire thing, from the bombing to the build-up to hearing that Fitzwallace is dead to seeing Donna in the hospital.
President Bartlet has to tell the President of Equatorial Kundu - a proud and intelligent man who nonetheless has come to the U.S. to beg for the life of his AIDS-stricken continent in the form of medical relief - that his government has fallen to a coup, his wife is in hiding, and his brother and two sons are dead. He is executed in the airport parking lot upon returning home at the end of the episode ("In This White House").
Towards the end of the second half of "In the Shadow of Two Gunmen," then-Governor Bartlet has a conversation with Josh the night that Bartlet wins the Illinois primary, sealing his position as the Democratic candidate for president and that Josh's father dies of a pulmonary embolism. It rings true of so many parts of grief, but these are the lines that always get me:
Josh: He liked that I was working for you, though. He liked that we were starting to do well. He would've liked tonight. At least all his friends and neighbors will be spared all the-
Bartlet: He'd be doing some bragging right about now?
Josh: Yeah. Your name wouldn't have come up, by the way. 'My son won the Illinois primary tonight.' [Beat] Another couple of hours, he'd've been able to say that. He'd have been proud.
Bartlet: He was already. Trust me Josh, I'm a father. He was already.
The episode "The State Dinner" ends with resolving a sub-plot, a U.S. naval fleet being caught in a bad hurricane. Bartlet is taken to a briefing room and put on the phone with the only ship with a working radio, a tender ship, and the only crewman available to detail what the fleet is dealing with, Signalman Third Class Harold Lewis. He's injured, scared, and very unsure of what to do. All the President can do is keep talking to him and let him know someone is on the other end. "Two Cathedrals" reveals that the ship went down with all hands lost.
The season six episode where Josh and Toby get into a fight—not the fight, but the scene afterward where C.J. and Toby talk and it's revealed that Toby isn't angry because his brother died of cancer, but because his brother committed suicide at the diagnosis. As Toby expresses his resentment that his brother killed himself when he could have had more time, and that his wife had to find his body, and that Toby doesn't want to look at a picture because he spent twelve hours guarding his body per Jewish tradition. All the while he is very gradually breaking down in grief... when C.J. asks if he'd like to be alone, he can just barely manage a whispered "No." Whatever you (or Richard Schiff) might think of the later seasons, that scene is powerfully acted.
The entire conversation between Toby and Judge Mendoza in "Celestial Navigation", when Toby goes to bail him out of jail after he's wrongfully arrested for drunk driving. Edward James Olmos' Tranquil Fury absolutely sells it.
Toby: One phone call, Judge. ďToby, this has happened. Tell Ďem my nameís Roberto Mendoza and the Presidentís named me to the bench!Ē Mondoza: They pulled me over because I look like my name is Roberto Mendoza and Iím coming to rob your house. Toby: Let's go. Mendoza: Where are we going? Toby: Home. Letís go home! Mendoza: Iím not going anywhere. Toby: Judge... Mendoza: Iím under arrest, Toby. Toby: Not anymore. Letís go. Mendoza: You pull all the strings you want, Toby, but not for me. Come Monday, Iím gonna avail myself of the criminal justice system for which I have worked my entire adult life. Toby: Judge, due respect: get your things and letís go. Mendoza: My kid was in the car, Toby! They patted me down and they handcuffed me in front of my nine year-old boy. Then he and his mother got to see them put me in the squad car and drive away. Toby: Heís also seen you wearing a robe with a gavel in your hand. Mendoza: He doesnít understand that. He doesnít know what that is. He understands what the police are, because he watches television. Thatís what heís gonna remember: his father being handcuffed. So America just got another pissed-off guy with dark skin. Toby: Robbie and Laura. Where are they right now? Mendoza: Motel a few miles— Toby: Thereís nothing about this that doesnít stink. If it were me, Iíd want to exact vengeance, and Iíd say ďLet justice be done.Ē Iíd also want to spend some time in a dark room alone, so that I didnít have to face my wife and my son and have them see my humiliation. Rob, I canít get this done if this is the story. Canít get it done. Nothing about this that doesnít stink. And nothing about it that wouldnít be better if you were a Supreme Court Justice. (beat) Let me take you to the motel. Go see your boy.