Tear Jerker / Hazbin Hotel: Lucifer's Folly

• Symere getting purged on Extermination Day of 2023. It's widely considered the most iconic tragic scene of Hazbin Hotel: Lucifer's Folly and for good reason. Not only was he the first Hotel patient to die, but he was also Jamell's younger brother. And it's stayed with him sense.
  • To make matters worse, Symere is later revived as a zombie by Dreadric but Jamell is forced to kill him again in order to reverse the zombie curse. And he still stays dead.
  • And then Symere is revived for a THIRD time and still remains dead by the end. You really just want to hug Jamell after being forced to see his younger brother die thrice (although given the third one was during a April Fool's event, the canonicity is debatable.)
  • Tellingly, despite him being killed off thrice it still always manages to be a huge tear jerker.
• Poxxy II's death in the second Angel Dust clones RP event. She was originally just a gag character who was created by Baxter because he couldn't get with Poxxy, she ends up going through a HeelRealization and then sacrifices herself to destroy most of the Angel Dust clone army, killing precisely 70% of them. And unlike the original Poxxy, she's just a clone meaning she can't come back.
• Cazador losing Alasmore and spending several days in a bar drinking his sorrows away. He was hit hard by the loss. To make matters worse, there are several bodies of Cazador laying on the floor, implying Cazador killed himself multiple times.
• Montgomery Python's entire story before he met up with Maggie Hellraiser. At first things seemed to go alright for him, but then he hooked up with Purr-Vert who not only was unreliable and enabled many of his more bad habits, she was also abusive towards him and demanding, causing Monty to overspend a lot of things for her. During this all, Purr-Vert also kept feeding Monty Python and not allow him to exercise much, causing him to bloat and gain an large amount of weight during this time to the point he was borderline recognizable. Before he can lose weight he's suddenly forced to go up against Rift Landshark finally in he loses in spectacularly due to not being in shape. After this, Purr-Vert then proceeds to claim Monty Python was sexually harassing her, causing Monty Python's reputation to tank and get blacklisted. Purr-Vert then proceeds to tell Monty Python off and leaves him, forcing Monty Python to work at fast food restaurant Hobo's Fried Rats for a while. It's easily one of the most tragic stories in all of Lucifer's Folly. Thankfully, once he meets Volk, Maggie Hellraiser and Jasper-Monty his life starts to turn around.