- Cecil's absolute terror and despair when management finally opens their doors and roams the radio station hunting for him in episode 3. Poor guy's on the verge of tears.
- In "One Year Later", when Cecil believes Carlos to be dead. He can't even bring himself to keep talking and sounds like he's on the brink of tears.
- Scoutmaster Harlan, who is taken away by the children in "Eternal Scouts". The last thing we hear from him? "We could have had something, Cecil." To add salt to the wound, this is the one thing Cecil has to say about it:
"I hope that he continues to be both proud and terrified in whichever new reality he finds himself. I think often about the last moments with him, and the things that were said."
- Made worse in Episode 36 when it's revealed that they were childhood best friends.
- The oddly bittersweet traffic in "The Man in the Tan Jacket":
"There is a car. It's not in Night Vale, or even in the desert which cradles our little town. It's out somewhere, beyond that. There are many cars there, but I'm speaking only about one- blue, squarish, with tires and windows and an engine that works most of the time. A woman is driving it, and she is also glancing whenever she can at the child in the passenger seat. He is a child, but he is 15. You understand. She is glancing at him, but she is not saying anything, and he is not saying anything either. She wants to cry or she wants to push him out of the car. Or, she wants to go back in time and insist on using a condom. Only she would never do that. She wouldn't change any of this, really. Not for all the money, piles of money, some of it defunct money from defunct and absent governments. She wouldn't give any of this back. So she drives her car, blue, squarish, with tires and windows and an engine that works most of the time. And she glances at the 15-year old child, and neither of them speaks."
- Episode 22's weather, "Winnifred" by Seth Boyer. It's a generally melancholy-sounding acoustic guitar piece that becomes even worse if you're a Joss Whedon fan and know that the lyrics are about Fred's death.
- As of Episode 32, Old Woman Josie's angel friends have inexplicably left Night Vale. She's not happy about it in the slightest.
- Extra heartbreaking when you remember that the Angels were around since the show started. Seeing them leave and hearing that poor Josie blames herself for it is deeply upsetting.
- Episode 33 has some cassette tapes with recordings Cecil made when he was 15. While they are mostly in turn adorable or creepy, they also give us some idea of what Cecil's home life was like.
"My mom seems really proud of me, too! She hid from me for three days, the longest time ever!"
- Another particularly heartbreaking (as well as creepy) line was after Cecil interrupts the tapes again. He sounds very unsure, shocked, and just a little bit sad.
"...I...don't...remember having a brother...?"
- "Some of us are not here. We leave space for them. Space that has been emptied by time."
- " Megan loves computer. Computer simulates love for Megan." OH GOD THE FEELS.
- And then, after he tells Megan he loves her (or at least tries his hardest to), after he promises he'll make the world a better, safer place for Megan, after he promises end all war, he's unplugged. And Megan...
A single, adult man's hand is slipping, sadly, down from the keys of a darkened computer. She scurries a little slower than before. Maybe her knuckles slump as she makes her way home through quiet streets.
- When asked for what she wanted, Megan simply answered "For everything to get better." And then Cecil goes on to say that it was cute, but "it's not like things will ever get better," which really says something about his outlook on life.
- When Cecil is bought by someone in "Auction". We don't know who did it, or why it only took one bid...but Cecil is absolutely terrified at the end, and while he wishes he knew who did it, would just settle for somebody making him feel better at that point.
- There's also this bit about death
And yes, you will die – but probably not until everyone you know is already dead, too. Your parents, your friends, your pets...each death leaving a small but irreparable scar on your not-yet-still, still-beating heart. The living tell the dying not to leave, and the dying do not listen. The dying tell us not to be sad for them, and we do not listen. The dialogue between the living and the dead is full of misunderstanding and silence.
- How "Numbers" ends. Fey turns out to be just a computer program, rebooted almost immediately and impossible to disconnect.
- "Oh, Fey... For you, freedom was never an option."
- Also, keep in mind the fact that Cecil clearly identifies with her situation and the StrexCorp take over...it must almost feel like it's saying that he's doomed to fail, also.
There is no worse fate than working for a radio station owned by an organization thats goals are not your own, constricted to the limited language they allow you, and relaying messages that you do not understand or agree with. That would be awful. A radio announcer put in that situation, such as… Fey… would be justified in escaping or overthrowing their management.
- "I can only do what so many of you can only do. I can only... listen. Listeners (and here I address also myself), remember our limitations. There are boundaries to all of our worlds. Fey, for instance, appears to be self-aware software trapped in a heavily defended metal box. But within our limitations there is no limit to how beautiful we can become; how much of our ideal self we can create. All the beauty in the world was made within the oppressive limitations of time and death and impermanence. And, Fey... you are so, so beautiful."
- From the same episode, Pamela Winchell finishes her latest emergency press conference showing us how sad she is about losing her job.
- "Visitor", and Cecil's grief over what happens to Khoshekh.
- In "Condos", the Faceless Old Woman tells a story about a woman who only observes and follows the behaviors of others in an attempt to become an ideal person. In the end, this women lives her entire life never having truly lived for herself. The Faceless Old Woman is quick to add that this is not a story about her, but she understands why you might think that it is.
- The end of "A Story About Them". The Man Who Is Not Short is killed by his partner, who can only tearfully say, "I'm sorry."
- The revelation that Old Woman Josie has inexplicably vanished.
- The post-weather revelation in "Parade Day" that no one but Tamika and her gang rose up against StrexCorp, leading to their arrest, with Cecil being extremely disappointed in the town for letting it happen.
- As of Episode 47, Cecil is gone.
- Episode 49 Part A: Cecil all but pleading for a way to get Carlos back home, particularly the uncharacteristically quiet way he says the following line:
"I would like Carlos to come home now..."
- Cecil's panicking when Carlos starts to fade, and Carlos's "Dana...I cant see Cecil anymore." He just sounds so heartbroken.
- Carlos is able to return Dana, Old Woman Josie, John Peters, and all the misplaced citizens back home, but he makes an important discovery: Exposing Night Vale to outside stimulus is enough to warp linear space and time. And guess who's not from Night Vale...?
Carlos: (audibly choking up) And I remembered... that I am not from Night Vale. I remembered that, as far as the laws of the universe are concerned, it is not where I belong...
- We don't actually hear Cecil listening to the voicemail. After the voicemail plays Cecil continues to give the news, and the podcast ends shortly after he says that there's a message from Carlos and he needs to listen to it. This only makes it worse, as we're left to imagine what his reaction was.
- Kevin talks about the Smiling God and how it took over Desert Bluffs in Episode 49 Part B. He cheerfully relates how Desert Bluffs fought it too, just like Night Vale did, but eventually, all the resisting citizens, including the radio host, were taken over.
- Episode 50: Carlos is still gone. Cecil sounds like he did in early episodes, speaking in a slow, borderline-monotone. He tries to get a reservation at Tourniquet. Table for... for just one, of course.
- A few people have also noted some Fridge Horror when they realize just how appropriate the weather is for the episode. The song happens to be about two lovers separated by death, but still in love and interacting with one another despite this. The parallels between the song and Cecil's and Carlos's plight of being in two different dimensional planes is uncanny.
- In episode 51, Cecil reads horoscopes again. Some of them are pretty funny. Others... not so much.
Aquarius: "Your boyfriend is trapped in an alternate desert dimension. It is difficult to say when he will return. Perhaps take up drinking while crying in a quiet room." Wow! That’s a very specific and... painful horoscope. Thanks for nothing, stars!
Taurus: "Someone misses you a lot, Taurus. And even though you have nothing but endless time trapped out in a nightmarish desert hellscape, you have a hard time making a phone call longer than ten minutes. Maybe call a bit more than you do, Taurus!" Yep, that’s just some astrological advice from the stars."
- As the new mayor, Dana seems to be slowly suffering the same fate as Pamela Winchell. That is to say, poor Dana will likely end up going completely and violently insane.
- Steve Carlsberg finally revealing why Cecil hates him with such a burning passion. On the day of Steve's wedding, he and Cecil actually got off to a great start; Cecil even complimented the scones Steve makes (from scratch!), the same ones he now publicly denounces. Then conversation turned to the vague-yet-menacing government agency, and Cecil instantly became enraged at Steve for trying to spread illegal information. He was about to call for the ceremony to be cancelled until his sister convinced him otherwise. And apparently, the hummus and pita chips he brings to PTA meetings are store-bought and people only eat them to be polite. It really forces the listener to see some uncomfortable truths, that Night Vale through the eyes of one man may not tell the whole story...
- Steve mentioning that seeing the "arrows and charts in the sky" have not made his life easier. Not at all.
- When Homecoming is cancelled, the pure sadness in Cecil's voice when he realizes that he won't be able to see his dead mother.
- It's clear as of episode 58 that the relationship between Carlos and Cecil is becoming somewhat strained.
- Earl Harlan doesn't know the name of his son.
- Cecil can't even pretend to be okay by the end of episode 61
- As of episode 62, someone's been mind-controlling Cecil and making him protect Mayor Dana. He's not even entirely aware of having done it, and he's afraid Dana might be the one doing it. He just sounds so broken by the end...
- In episode 64, Cecil's depression after the Glow Cloud accidentally destroys his water color painting of Carlos. It's clear how much that painting meant to him.
- Episode 65 has Fey trying to call Cecil, but she keeps lapsing back into the numbers.
- Later on, Dana calls trying to convince Cecil that she's not the one who bought him at the auction. She might be lying, but she just sounds so depressed about it. She also notes that she and Cecil talked more when she was trapped in the dog park, apparently worried that they're drifting apart.
- Episode 67: [Best Of?]: Poor, poor Simone Rigadeau. She used to be the earth sciences professor of Night Vale Community College, and then started receiving visions of a timeline where the world ended (specifically, the one where Nulogorsk got nuked). She quit her job and became a homeless transient because she is trying to piece together her fractured psyche, but still lives in her old building possibly out of a longing for the life she lost.
- Hearing Cecil describe Leonard Burton's brutal demise is really hard to listen to, and his death apparently affected the entire town to a similar degree. Slides into Nightmare Fuel when you realize that he died during the Clinton Administration, leaving the question of who has been broadcasting the show this whole time?
- And now as of episode 69 Cecil has grown sick of Night Vale, of his life constantly being endangered and manipulated, and plans to move to the desert otherworld permanently.
- Depending on how you feel about Kevin, the end of Episode 70A is this - Carlos' letter telling Kevin he's leaving him and the Otherworld to return to Night Vale leaves Kevin feeling not only sad, but terrified - it's likely this is the first he's felt sadness since he was corrupted by the Smiling God and he does NOT like it.
- Even though Violet was the one who bought Cecil at the auction to use him against his will, he has a pretty sad reason for doing so; given that he only has 1/5 control of his own body on a good day, and the other 4/5 are hell bent on revenge, it makes it really hard for a dragon to want to live a normal (for a literal five headed dragon) life. He just wanted to get his other four heads to agree to leave their petty squabble behind, and only through using Cecil to foil their plots with the Faceless Old Woman was he able to make any headway. Poor thing.
- It's made even worse when Violet takes all of Cecil's arguments and throws them back at him, not only when Cecil is angry about not being able to control his body, but also when he complains about losing his friendship with Dana. Without Violet taking matter into his hands, he would have lost Dana herself and not just the friendship he ruined by not trusting her.
- Episode 73: Triptych - We finally get to hear some more from Kevin, and all of it is really exceptionally heart-rending. Due to a Timey-Wimey Ball affecting Cecil's setup, we get to hear Kevin from three different points in his life; the first is him Pre-Strex, when Desert Bluffs was so much like Night Vale and Kevin was a genuine person with pride in his town; ya know, like Cecil. The second time is during the events of the Strex takeover of Night Vale, and it is apparently this conversation that led to Daniel and Lauren being sent to Night Vale. The final time, Kevin is a broken shell of a man, possibly aged beyond his ability to tolerate it, trapped in a wastescape with only his fractured psyche and the ebbing influence of the Smiling God for company. Poor bastard needs a hug.
- Also, the fact that Cecil lied to Kevin 1 about his ability to fight off Strex to give him false hope at the end of the episode. And the worst part is, he wasn't technically lying; Kevin and the inhabitants of Desert Bluffs do get to live happily after the battle against Strex, but not with a happiness they know.
- There's something strangely sad about the tarantula's entire situation in the novel; reacting instinctively to simple stimuli in a manner that suggests an understanding it lacks, occasionally interacting with Catharine and building up to an ultimate fate that, when it comes, borders on the nightmarish.
She opened the box. Inside was the mangled body of a tarantula. It had been hacked over and over until most of its body had detached from itself, a jigsaw puzzle way past solving. [...] Jackie tossed the box in the trash, wincing as she did.
Somewhere, Catharine felt better. Nowhere, the tarantula felt nothing at all.
- In "Cooking Stuff: Thanksgiving Special", Earl discusses with Cecil the difficulties raising a son he didn't know he had until the previous fall. There's no record of Roger's existence, apparently no birth mother, he gets picked on at school, and doesn't remember anything from before showing up at his father's door. Even when Cecil tries to assure Earl that he's a good father, Earl hopelessly admits he has no idea how to connect with his son or help him deal with his many issues.
- Basimah Bashara's father left to fight in the Blood Space War when she was six years old. He can only communicate with her through letters sent from thousands of years in the future, meaning that she's already long dead at the time he's writing them. While she does love her dad, she resents that he didn't stay to watch her grow up and that they're practically strangers to each other. All she really wants is for him to come home... and he does!
- Made more heartbreaking by the fact that Basimah is a completely normal and relatable teenager. Replace "Space" with, say, "Afghanistan" and take out a couple token pieces of Night Vale weirdness, and her story is the same as that of thousands of soldier's kids in the real world.
- In One Normal Town, Cecil reveals that he's still traumatized over that time he was sold to Violet Head for auction.
- Episode 86 reveals a tragic detail in the past of John Peters - you know, the farmer? - in that he has a brother. Who signed on to be in the Blood-Space war, and only know is John getting cards from his brother. The card was supposed to arrive when he was 12, and only just now did he get it.
- Episode 87: The Trial of Hiram McDaniels - As the title would imply, this is indeed the Trial that we've all been waiting for, to see justice served and to see Violet finally get some recompense for the years of having to put up with his other heads. And then we get the verdict; death for the other four heads, and since Violet is connected to them wholly, he will die as well. Goddammit, Joseph! We trusted you!