- The Secrets That I Keep, a collection of secrets that show Strong Bad and Strong Sad getting along.
- 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.
- 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. 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 F*CKING PRANK SHE WANTED TO PULL ON STRONG BAD. If there was a "Rage-Stoker" page, this would be on there.
- What an Idiot!? Unintentionally Unsympathetic?
Tear Jerker / Homestar Runner