Entries 20 and 54 can be considered fridge tear jerkers, because they give us glimpses of the person Alex used to be: a friendly, playful young man with a dry sense of humor and a penchant for making bad movies. Then the Operator comes into his life, hijacks his entire personality, and twists him into a murderous madman.
Tim's emotional What the Hell, Hero? rant to Jay, calling him out on Jay's complete lack of anything productive regarding the investigation, and on making Tim's condition worsen by reappearing in Tim's life. Tim's voice audibly cracks several times, especially when he describes how his life has gone to hell over the past three years, due to Slendy's Laser-Guided Amnesia.
And on top of that, when he leaves, you can just feel Jay saying to himself, "I'm alone." Any help he might have had from anyone, his last thread of hope in finding someone who shares his pain, whose life has been just as ruined as his, who could work with him to discover more or even to end the malign influence on their lives...all gone. In fact, he appears to be wiping away tears.
And before all that, Jessica confessing to having the same symptoms as Jay. Both the confession itself, with Jessica clearly scared out of her mind, and then her later disappearance. Once again, Jay finally finds someone who could understand, only for them to be ripped away... only this time he shows signs of self blame for getting her involved in the whole debacle in the first place.
Entry #60 reveals that Tim has experienced the health issues that are currently present in him since childhood. (The medical record that was shown was dated to 1995). Just think about that for a second. This sickness he has been shown to have has been going on for the majority of his life. The line he said in Entry #59 makes this hit home even more. "And I start getting better. And I can hold steady work, I can function like a normal human being for once in my life."
Entry #60.5 delves deeper into Tim's mental health: the problems he's been experiencing since childhood include insomnia, hallucinations, headaches bad enough to cause him to scream, and the inability to experience pleasure or happiness.
We have never, in the course of the series, heard Tim laugh with genuine humor, or seen him smile with genuine pleasure.
Not entirely true. In Entry #58, Tim does seem genuinely happy to show Jay the abandoned hospital from Entry #56... then Jay insists on going to the one Brian disappeared in and Tim returns to his bitter self.
Some of Jay's tweets really show just how screwed up his life has become.
On twitter someone outright asks him— "Why don't you bring someone [into the ominous tunnel]?" His answer: "I have no one."
Totheark's "Observation" entry shows Tim in a moment of possibly suicidal despair.
entry/Entry 61 could be considered one. Seeing Tim so frantic, obviously in pain, and even breaking down sobbing before he wanders off as Masky again is heartbreaking. It's almost as if he realizes it's happening again, and knows he's powerless to stop it.
Look carefully when Hoody opens the box on Tim's bedside table: aside from the empty pill bottle, it also contains a razor blade. And Tim's medical records indicated that he was a suicide risk.Oh, dear....
In Entry #65, right as Tim is taking the pills, you can see a scar on his wrist.
Slightly less depressing theory: some people use razor blades to cut pills in half, such as when their dosage has been adjusted.
Unlikely, seeing as Tim's pills are capsules, not tablets. Either he's self-harming, or he has a death wish.
Or he could have razor blades for some other purpose. This one knows a lot of people who prefer loose razor blades to mounting them in a razor because they feel it offers them more precision and control.
Hoody's actions get a bit more tragic in light of later entries, which imply that he's suffering from full-fledged Slendersickness and stole the pills because he desperately needed them himself — and that he wanted to force Tim to relapse because he desperately wants his only friend and ally back by his side.
A brief moment in Entry #63: Jay, while waiting in his car, dials a number only to be unable to reach it. The look on his face suggests it's not the first time, and the talk he has with Tim suggests that it's probably Jessica's number. He's been trying to call her all this time in hopes that maybe, just maybe, she'll pick up.
He also mentions that it's been a year and a half since she's disappeared. Then he forms an alliance with Tim on the condition that he helps him find Jessica. Despite not knowing her that well, he really seems to care about her very much, and he's had to live with her disappearance for so long with little to no clues.
Entry #64: the Operator is coming towards Tim and Jay, while Tim is incapacitated in a coughing fit and Jay is desperately trying to drag him away. Tim can barely speak, but he manages to tell Jay, "Run!"
Which makes it that much worse when Jay finds Tim waiting in his car...and Tim only gives him a Death Glare before driving off.
The desperation in Jay's voice as he shouts after Tim is palpable. Just when he's found an ally, just when he's making some progress, just when he's close to finally getting some answers...it's all snatched away from him. Again.
Entry #65: The first four minutes or so are Tearjerker meets horror. The rest of the entry is mostly the former.
Special shoutout to Tim in the burnt-out hospital, sobbing and having apparently reverted to a five-year-old mentality.
Even moreso when Tim starts to cough and proceeds to swallow his entire bottle of pills in one giant handful.
Jay's comment of "I'm not really a trusting person anymore, Tim." The tone in his voice is just heartbreaking.
The subtext to Jay's Twitter post about the woman in ToTheArk's videos: he has been poring over them as much as we have, desperate to find anything resembling a hint about Jessica's whereabouts.
Entry #66: Tim blaming himself for the mess that the Operator has caused for everyone. Also, we find out that Brian was his first real friend. They met in college.
Tim's body language...the hunched shoulders, the near-quivering as he's back in his old hospital room. He's scared and near-broken. That's some truly great acting right there.
Entry #68 We see Hoodie's sparse living conditions, and it's strongly implied that he is a victim of the Operator too. Its a great humanising moment for the character, and is enough to make you feel sorry for the guy.
Entry #70: Alex did everything he did in order to protect Amy from the Operator. As we saw earlier, it seems that he failed in that mission.
Entry #71: Jay learns two very important things: That he cannot trust his own memory, and in one of the blackouts that he cannot remember, Alex beat him senseless and left him to the Operator's tender mercies.
entry #73: We find out that Hoodie needs the same medication Tim needs, which requires him to scrounge his hiding spots repeatedly and steal it from peoples' houses if it comes to it. While his goals are still unclear, like Entry #68, it's humanizing for him and it's hard not to feel sorry for him.
Entry #75: Jay has attacked Tim and, feeling betrayed that Tim was keeping secrets from him, has left him behind. Jay really is alone now, with no home, no friends, and Tim has implied that if he watches the tape, that things will get even worse.
Entry #76: Things got worse. The search for Jessica was hopeless all along; Alex killed her and left her corpse for the Operator around the time Jay left the hotel they were at, and apparently Tim had something to do with it.
Masky wasn't attacking Jessica in the hotel; he was protecting her. Likewise, Hoody stood guard over her until she woke up, and stayed with her until Alex drove him off at gunpoint. Even with that, he still followed them and waited for an opening to allow Jessica to escape. And with all that, she still ends up attacked and left on the side of the road, Masky getting to her mere seconds after she was taken by the Operator. Masky's aura of failure is almost palpable in the aftermath of that, as he slowly takes off his mask and stands there, likely blaming Jay and Alex for slowing him down with that broken leg, which is what stopped him from getting there in time to save her from getting taken.
It's even worse than that. Jay saw the tape and seems to blame Tim for it, despite it being clear that A) Tim wasn't himself, literally, and B) Masky was trying to save Jessica. Jay's sanity has slipped that far.
Entry #77: Just when it seemed like they were becoming friends, Jay's recent paranoia and Sanity Slippage has caused him to slip so far from the protagonist we've always known him as that as a result, Tim has taken his camera, left him tied up in his house, and has now taken over the Youtube channel.
Probably something everyone saw coming, but it doesn't lessen the impact. In Entry 80, Jay enters the building where Alex supposedly is. Jay finds Alex but is shot immediately, and is presumably taken away by the Operator. Tim has taken over the channel and the final words in the entry are heartbreaking and simple. "I don't know what to do."
And before that:
Tim: This wasn't supposed to happen.
Tim running through the building, desperately searching for Jay, crying out for him after finding the camera and the bloodstain. You can hear the heartbreak and failure in his voice, knowing that he unintentionally led the closest thing he's ever had to an ally to a horrific fate.
Entry 81 ends with the reveal that someone stole all of Tim's medication from his bag. The medication that is the only thing preventing him from turning into Masky. His only known protection from the influence of the Operator. Tim is not only completely alone now, he is also totally defenseless against his enemies.
Entry #82:Tim finds a video on Jay's laptop that that takes place a day before #77. Jay calls Tim from Rosswood and leaves a message saying that he's sorry and wants to patch things up between them. But then The Operator attacks him, presumably causing his violent and unhinged behavior in #77. If that hadn't happened, Tim and Jay would've worked things out, and the terrible chain of events that happened (including Jay's apparent death) might have been prevented. Even worse, Tim never got that message.
Entry #83: Tim is at the college, possibly retracing Jay's steps. in the midst of a severe coughing fit, he hears movement, and immediately calls out Jay's name. Hoping against hope that Jay somehow escaped The Operator like Tim did in #65. He didn't.
Entry #84 seems innocent, showing Tim and Brian auditioning for Alex's movie. But at the end, Tim realizes that Brian is wearing the same sweater as the Hooded Masked Man. This leaves him to question one thing: If he had known that Brian, his best friend, was totheark, would he still have killed him? In the end, he says that he knows Alex is watching the video, and dares him to come find him.
A relatively minor one, but given that he wasn't a murderous psycho at the time, I felt bad for Alex when it became clear that nobody besides Brian and Tim were coming to his auditions.