A suicidally depressed man being lead to various fun places in an effort to talk him out of killing himself? Not funny. Said suicidally depressed man nonchalantly holding a revolver to his temple the entire time, even when sitting down for dinner or on the various rides at an amusement park? Actually Pretty Funny.
Desmond sincerely asking Pim if spending time with Pim's dysfunctional family is supposed make him not want to kill himself.
The fact that, for all Charlie and Pim's efforts to cheer Desmond up through nice, friendly things, what actually snaps him out of his funk and helps him find a new purpose in life is shooting a small creature in the face at point-blank range, then starting a whole business dedicated to exterminating them in the least humane ways possible, which wouldn't be nearly as funny if the bliblies weren't violent annoying pests.
Charlie attempts to improve Shrimp's look by taking him out to buy some new clothes? Basic sitcom stuff. His reaction to Shrimpy showing off the Badass Longcoat he put on? Horrifically dark and hilarious.
Smormu’s ‘In Memoriam’ photo being a picture of his bruised corpse on a slab in the morgue.
The Halloween themed episode takes this to extreme measures with its climax. The main antagonist of the episode (a forest demon dwelling in the woods) ends up being outed as someone wearing blackface at the Halloween party (despite his whole appearance being black). Having him try to defend himself by actually talking normally (albeit with a deep voice) and explaining that he's an actual forest demon while being recorded for social media purposes, then being killed afterwards and roasted up as food is straight up wrong on all levels, but considering the fact he almost ended up killing Pim and the fact that he's one of the scariest characters on the show, and you suddenly realize that he deserved such a gruesome fate.
Charlie: (completely nonchalant) See, that's exactly why I don't dress up for Halloween. That right there, that's the reason.
Those familiar with Björk may know of the terrifying story of Ricardo Lopez, a crazed fan of the singer's who mailed her a letter bomb and committed suicide in a mad gambit to be Together in Death with her. The entire ordeal is as disturbing as it sounds... and yet Hadel managed to spin the story into a hysterical fantasy by making Lopez a Hobbit, renaming him "Mip", and making Charlie and Pim the unfortunate messengers of his murder-suicide scheme. Adding onto this is Charlie's and Pim's viscerally realistic responses to finding out that Mip's "gift" for the Princess was actually an IED.
Charlie: OH MY GOD! That was a bomb the whole time?! Pim: JESUS CHRIST!
Mr. Man complaining that he actually wanted to kill the Puerto Ricans after Grim shows his true cowardly nature and breaks down, begging for mercy after the Boss aims an M16 at him, especially since his voice actor Lyle Rath is of Puerto Rican heritage.
The first season finale contains a fairly subtle one. Having a character imply that Christianity is the only correct religion? Horribly insensitive. Having Joshua Tomar, who is Jewish, say the following line at the end of the first season? Absolutely hilarious.
Grandfather Glep: Yup. Hell is actually real, and Christianity was right all along. Sorry! [...] Merry Christmas, everyone!
At the climax of the season two premiere, seeing the video game CEO violently convulse on the floor after being stabbed in the head by Charlie's client (who, moments prior, threatened to saw off Charlie's head) is a little disturbing. This is quickly nullified when the CEO's final conscious act is to dip one final chicken nugget in his own blood and eat it before promptly dying.
Gwimbly discovering that his close friend Mr. Millipede is dead? Heartbreaking. The tombstone depicting Mr. Millipede's likeness, which is a low-poly cartoon bug with a goofy smile? Funny. Gwimbly stating afterwards that this cartoon bug died from something as uncomfortably realistic as a fentanyl overdose? Darkly hilarious.
