- The Secrets That I Keep, a collection of secrets that show Strong Bad and Strong Sad getting along. It's really depressing how much their relationship got derailed.
- Strong Sad's blog. Some of the content is pretty funny, as Strong Sad has a dry sense of humor and leads a very strange life, but most of it is shockingly dark for Homestar. Strong Sad is shown to be pitifully lonely, nearly emotionless, severely abused, obsessed with counting, and prone to wasting hours of his time on pointless tasks, and he has bizarre and eclectic tastes, no talent in anything, and no drive to do anything.
- "Sick Day." You can't help but feel sorry for everyone in this one. Strong Bad is so ill that he's taken refuge under his desk and is rendered incapable of answering the latest email, The Cheat is sobbing in a bucket of puke, and Strong Mad is crying for help in his quarantined room. Homestar's ill to a delirious extent as well, though it's hard to tell if that's just his normal countenance or if it's compounded by his sickness.
- An in-universe example in "Homestarloween Party"; everyone takes turns in adding to a supposedly scary story, and when it's finally Strong Sad's turn there's a robot and the Goblin. Strong Sad's addition to the story results in the formerly-human robot remembering its humanity, crying, shorting itself out, and crushing its two human grandchildren and the Goblin. "And none of them lived." Everyone else (except for Strong Bad and Homestar) is reduced to tears, and Marzipan tells Strong Sad that he's banned from next year's party.
- At the end of "A Decemberween Mackerel", Homsar is seen dying in the snow.
- The April Fools' 2014 toon, which was the first toon in nearly four years, can easily strike a chord. It starts out with the once-happy page welcome screen having fallen apart, then goes through a number of features from the site's older days that the same people who would rejoice at an update in the first place are bound to remember fondly. At the end, there's a reprise of the already-heartbreaking Homestar Windows 98 Shutdown Song, and Homestar and Strong Bad just chipperly discuss the possibility of another update in three, five, maybe fifteen years. It gets worse in an Easter Egg, where they reveal that they've done absolutely nothing with their lives in all this time, Homestar himself even living in a moldy duffel bag, although it could just be a reference to his puppet self having been stored in one.
- The Halloween short "I Killed Pom-Pom!" revolves around Homestar mistakenly believing he killed Pom-Pom. In the end, he accidentally does kill Pom-Pom.
- We get two big reveals in the longest cartoon to date, the 2016 April Fools special Marzipan's Answering Machine Version 17.2; both of which are O.O.C. Is Serious Business. First, Homsar calls and reveals that he can speak coherently on the phone for some reason. He considers his non-sequitir ramblings to be "garbage" and he wishes that he could have a "constructive conversation" with someone. Second, the Poopsmith breaks his vow of silence again to admit that he thinks he has wasted his life "smithing poop." He ends his message by saying he will go back to being The Silent Bob once he hangs up.Poopsmith: It was nice talking to you. It was nice...talking.
- Subtly depressing are the calls from Strong Sad (as usual). He's so determined to be unhappy.
- There's also the last call from the recently incarcerated Coach Z. After he gives Marzipan instructions on where to find exonerating evidence, he tearfully remarks that he's glad that Marzipan will retrieve the evidence "right after listenin' to this and not wait five or six years"... not knowing that Marzipan will be away from her answering machine for several years.
- Then you remember Marzipan isn't at her answering machine because of a petty prank. Think of all the characters she could've helped: Homsar could've talked to her and have normal conversations, Strong Sad could be told by Marzipan to not try and define himself by a single quirk, the Poopsmith could've found new happiness in life, and Coach Z wouldn't be in prison for crimes he didn't commit. All this life-changing stuff lost, BECAUSE OF A FREAKING PRANK SHE WANTED TO PULL ON STRONG BAD. If there was a "Rage-Stoker" page, this would be on there.
- Powered by The Cheat doesn't seem like this initially, being a fairly silly example of Stylistic Suck, but their constant, absurd depictions of the Cheat receiving random praise and fame pack up until it gradually becomes obvious that they're only created by the Cheat to make up for his lack of recognition and abuse by Strong Bad by serving as delusional power fantasies. To show this further, when he made a cartoon Strong Bad liked but didn't consider worthy of a pizza or trophy, (Maybe a pizza trophy), he just gave a heart-broken sigh before making his own. In spite of the Cheat being a criminal and just kind of a jerk in general, it's rather depressing.
- Senor Cardgage. Apart from being a mentally challenged homeless man, one gets the impression that he's a version of Strong Bad if he didn't lose the bad attitude which is apparently keeping him from marriage and starting a family. During the email where Senor Cardgage makes a character video, he introduces the viewers to the "family might/could", which are really just a bunch of drawings made in the folds of his skin. Funny as it sounds, one gets the impression that Cardgage is so desperate for a family and a world where he regularly communicates with attractive women (perhaps why he calls people by the names of women when almost none of them are, in fact, women), that he's retreated into insanity to experience some vague semblance of having the family he might have had or could have had.
- The King Of Town, a doting old man with no actual authority (Despite inexplicably having a castle.) and who constantly attempts to garner praise from the residents of Free Country, USA through endless hair-brained schemes. He's morbidly obese and gluttonous, with no impulse control whatsoever, to the point where he once admitted to eating whatsit, and his memory is failing, to the point where He admits that it's completely possible Marzipan might be his daughter, but he literally can't remember and all his DNA is replaced with MSG. Even worse, the email 'origin' shows that he used to be relatively mentally sound and healthy only a few years ago, leaving why he's become this way rather unclear. (The fishsticks might have done it.)
- A day after the death of Daniel Johnston, the official Strong Bad Twitter account posted a piano cover of Johnstons Some Things Last A Long Time performed by Strong Sad. While the original song was already downbeat, hearing it sung by the websites resident woobie makes it all the more poignant. For additional tear-jerking, Strong Sad breaks down crying immediately after finishing the song. Even in-universe, Strong Bad was too moved by the performance to bully Strong Sad as usual. Of course, that didn't stop him from resuming the bullying the next day.
Tear Jerker / Homestar Runner