If you [[UnsympatheticComedyProtagonist ever have any sympathy for any characters]], there are some moments:
* The Depressing Comic Week ones, when they don't [[CrossesTheLineTwice cross the line back into being funny]] ([[BlackComedy in a horrible and twisted way]]).
** [[http://www.explosm.net/comics/1779/ This one in particular.]]
** Or [[http://www.explosm.net/comics/1777/ this one.]]
** Or [[http://www.explosm.net/comics/2016/ this one]]. Bordering on NightmareFuel and, as one comment notes, FridgeHorror.
** Or [[http://www.explosm.net/comics/2015/ this one]].
** If you spend a lot of time reading webcomics, [[http://www.explosm.net/comics/1778/ this one]] is particularly wrenching.
** [[MercyKill especially]] [[http://www.explosm.net/comics/2383/ this one]].
** So, it's daddy's first day as a [[http://www.explosm.net/comics/2998/ policeman]]...
** [[http://www.explosm.net/comics/1244/ This one]], especially the fourth panel.
** [[http://explosm.net/comics/4000 There's nothing worse than too late]].
** [[http://explosm.net/comics/3996/ A kid confronts his deceased father]].
** [[http://explosm.net/comics/4130/ An odd case of]] AndIMustScream.
---> '''AAAAAH! AAAAAAH!''' [[note]]I love you too, daddy.[[/note]]
** [[http://explosm.net/comics/4770/ This one]] would have been depressing on its own, but at the end it provides another depressing twist.
** They've even made a book of these.
* Also, the latter part of [[https://www.youtube.com/watch?v=HLI2-kYMUEE Waiting for the Bus]], in a weird way.
** The saddest bit is the 50 mph Man [[spoiler: loses the Indy 500]] and soon becomes [[spoiler: a total wreck, with alcohol abuse and smashing all his trophies. Eventually he robs a liquor store, ends up in jail and his wife is forced to divorce him. He soon becomes an old man sitting in the former stadium dedicated to him. Then one day, in a rainy night, he starts running again...[[DownerEnding only to commit suicide by smashing into a wall.]] Soon, the stadium becomes a memorial park. The Bus Driver stops and sees the sign...weeps...[[MoodWhiplash and then the]] [[BrickJoke bus explodes.]] What a DownerEnding.]]
* The Barbershop Quartet [[http://www.youtube.com/watch?v=BPY6lAX9RvM fail to save a man.]]
* [[https://www.youtube.com/watch?v=5wbHuqYKODo Grandpa's Storytime]], It starts nice, pretty much with the perfect setup for an average C&H short. But it goes from horror and surprise to sadness and wondering what will happen to the kids after ridiculously quick.
* The short [[https://www.youtube.com/watch?v=5T03fGBnOjo Missing Daughter]] goes from one Tear Jerker at the beginning to a completely different one halfway through.
* [[https://www.youtube.com/watch?v=IlCfkY4ZJ6I This video]], with the SarcasticTitle of "[[BilingualBonus La Comédie]]", features a clown being forced into prostitution. The look on the clown's face at the end says it all.
* [[http://www.youtube.com/watch?v=Vw8xjDgxzK0 Sad Larry,]] [[http://www.youtube.com/watch?v=RQ-w61_mzyA Sad, Sad Larry,]] [[http://www.youtube.com/watch?v=iXI1yHP6urk It's A Sad Christmas, Larry]], and [[https://www.youtube.com/watch?v=YFX035FYUFA he even falls]] [[HopeSpot in love]] at some point!
** To elaborate, Larry is essentially depressed. ''[[UpToEleven Very]]'' depressed. [[spoiler:So depressed that his co-worker fails to cheer him up... and promptly [[KickTheDog kicks Larry's food into his face and angrily leaves]]]]. The worst part is that this is TruthInTelevision.
** Sad, Sad Larry continues with [[CosmicPlaything Larry]] finally [[spoiler:attempting suicide. Of course, the series would be over very quickly if he actually succeeded, so his first attempt fails [[BungledSuicide by having his drop from a hundred-story building send him right into a conveniently-passing dump truck filled with pillows]]. Then, once regaining awareness of the situation, turns his head to see the building he works in being demolished, with no warning or reason. Cut to Larry being wished goodnight by his dad, thus revealing his status as a BasementDweller, and him sneaking into the garage to commit suicide by leaving the car running with exhaust pouring in. Cue his parents sneaking into the garage to have sex on the hood.]] Larry's expression says it all. Even ''worse'' is that even though [[spoiler:they're fully aware their suicidally depressed son is watching, [[KickTheDog they keep doing it. In FRONT of him.]] Cut to the next day, where on the TV, the [[NamesToRunAwayFromReallyFast Delberry Dismemberer]] is on the loose with his chainsaw. Larry tries to hang himself in the living room, but fails once again when his weight yanks the ceiling fan out of the ceiling onto him... and then his father, eating a sandwich in the bathtub, falls through the ceiling on top of him... This leaves Larry hospitalized in a full-body cast, unable to move. Cue the Delberry Dismemberer [[NightmareFuel rampaging through the hospital]], hacking people to death. We finally see Larry show some [[HopeSpot hope]] in his eyes... The Dismemberer, however, decides to simply leave him there [[ForcedToWatch to watch the entire thing]].]]
** "It's a Sad Christmas, Larry" begins with our favorite CosmicPlaything [[spoiler:being offered a gift by his friend, which turns out to be a pair of oversized fuzzy dice... for the [[FunnyAneurysmMoment car that was totaled in a recent accident]]. Larry tries to play it off - barely - and then takes a sip from a mug he was given that reads "Daddy's Boy." Cue exposition that his dad was fatally injured in the accident and is now on his deathbed. Larry's friend tries to console him by explaining that his own dad's in the hospital too, most likely not going to make it either... only for [[ConsolationBackfire the hospital to call, confirming that his dad will be home for Christmas]]. Within the next few hours, the father arrives, and immediately yells "You're not my son!" at Larry, [[KickTheDog hitting a sore spot]]. Fast-forward to dinnertime, and Larry is all but forced to say grace and give thanks for [[BlatantLies all the good things in his life]]. After being stopped by his friend, the hospital calls once again to put Larry's father on the phone. Larry's dad is about to die, and decides to use his last words... to [[YankTheDogsChain tell his son that he's pretty much to blame for the situation]] before flatlining. His friend says to feel free to dig in once he's done crying. [[DespairEventHorizon Larry begins to zone out completely and have vivid flashbacks of the accident]], before being asked a question by his friend about whether or not he would do "something like that." Larry's answer gets him [[DownerEnding promptly thrown out of the house into the snow.]] The screen pans out to show that [[CrossesTheLineTwice he was in a wheelchair the entire time]].]]
** "Sad Larry in Love" begins with Larry being in a movie theater watching a cheesy 40s romance film. [[spoiler:The film has a cheesy ending, obnoxiously stating that anyone who lives alone with no love in their life is a loser. Larry decides to try and find a girlfriend, and first looks outside the theatre when he sees a girl in the rain. He gives her his umbrella, which she takes for herself and trots over to her boyfriend, leaving [[UngratefulBastard Larry in the rain]]. Cut to the next day, in which he tries using a dating app online, and promptly gets [[AllMenArePerverts banned from the website]] for "harrassing"[[note]]He 'liked' a girl's picture[[/note]] members. Cut to a sombre walk in the park, where [[YankTheDogsChain seemingly]] ''[[YankTheDogsChain anything]]'' [[YankTheDogsChain that breathes has a partner to cuddle with/bone]], until Larry reaches the Diner. He's not even safe in ''there,'' since the food he orders is essentially in pairs. [[HopeSpot He then hears someone exclaim "Sad Mary?"]] He calls her over, and tries to deliver the same cheesy line from the movie he watched earlier to charm her. [[ComplimentBackfire Mary assumes he's making fun of her]] and promptly slams his food in his face, before running off sobbing.]] And in TheStinger? [[spoiler:[[HopeSpot Larry's dating app says they found him a match]]. ''Himself''. He continues bawling.]]
* [[http://explosm.net/comics/3752/ These comics are like a prison...]]
* [[https://www.youtube.com/watch?v=N_708QY7Obk The Depressing Episode]]. They are not kidding.
** A man is asking another unseen person whether or not they are alone in the universe. The camera pans out to show that he is talking to a grave.
** The opening of the show starts after with a bird flying around the title [[MoodWhiplash before crashing into the window as the man opens his door as the music becomes more somber]]. The man bends over to the bird before we are treated to a flashback of he and his mother find a dead bird lying on the ground when he was a child. As they comfort each other, he hears a baby bird chirping from a nearby nest, and they adopt it as a pet, whom he raises. [[spoiler:One day as he returns home, he sees an ambulance outside his home and, in the hospital, he is told that his mother had passed away. At her grave, the now adult bird flies off. We are then returned to the modern day, and the man now buries the dead bird next to his mother's grave.]]
** A tree has the words "Jimmy+Anna" with a heart shape carved around it. A man stumbles from behind the tree with a pocket knife and scratches the second name out. [[spoiler:He then bursts into tears as the next shot reveals that his car had collided with the tree, killing Anna who had been in the passenger seat.]]
*** [[spoiler:Later in the episode, we go back into this skit with a memorial placed under the tree. Jimmy walks over to it with a bouquet of flowers that he places down next to a picture of Anna. He looks at the picture and smiles, then crosses his own name out and [[DrivenToSuicide throws a noose over a branch...]]]]
** A man returns home from a trip and thinks that a line of food is for a surprise party. [[spoiler:His mother reveals that the food is for a funeral, as his father had committed suicide while he was away. Horrified, he looks over and sees his family grieving over a coffin. His mother then hands him a note saying that it was left for him, reading "Surprise - Dad".]]
** A man and a woman are crossing the street, when the man notices a car headed straight at her. He quickly pushes her out of the way [[spoiler:and the car stops in front of him. The concerned driver gets out, and we see that the woman is lying motionless on the ground. The man cradles her and silently yells to a group of onlookers. The next scene is a pan-over of pictures and awards she had won before it's revealed that she's now wheelchair-bound and in a vegetative state, as the man glumly brushes her hair.]]
** An elderly woman in a nursing home just trying to eat the peas on her dinner plate, but her shaking hands won't allow her to pick them up long enough to eat them. Made even worse when she defiantly refuses help, and finds that she really can't do it by herself, leading her to collapse in sobs and pound the table.
** A man has cancer, much to the dismay of both he and his newly pregnant girlfriend. The shots alternate between check-ups with his doctor and picking out a coffin (which depresses their moods, and with him looking worse in each shot) with check-ups on their baby in utero, picking out names among other things. At one point, the man is hospitalized and the woman gives birth. [[spoiler:The baby doesn't live very long, and ultimately flat-lines as the father holds its tiny hand.]]
*** Oddly enough, this is the only sketch with any sort of joke: [[spoiler: his weirdly small face. One might even laugh at the beginning with the whole "if your hand is bigger than your face" routine, given the absurdity.]] The rest, however, is pure sadness.
* [[http://explosm.net/comics/4128 Terrible things can happen to those who are young.]]
* [[http://explosm.net/comics/2019/ Those vultures aren't preying...]]
* In late August 2017, Kris began a series of comics (starting [[http://explosm.net/comics/4704/ here]] and ending [[http://explosm.net/comics/4724/ here]]) revolving around a man named Jim discovering that his son is the result of an affair with his wife. Understandably shocked, he runs off and plans to off himself after [[DrowningMySorrows drowning his sorrows]] and settling in a motel, but after seeing a family of ducks with a squirrel in the middle, he decides not to. The story ends with Jim divorcing his wife and getting the hard parts out of the way, and returning to his son for a heartfelt reunion. [[spoiler:Nope. The second stack of panels in the ending is a DyingDream as Jim bleeds out from self-inflicted wounds in the motel, as seen in the [[http://files.explosm.net/comics/Kris/mailman7_cyanide.png secret comic embedded in the final panel.]] At the top of that comic is another hidden comic... except, it's the first comic of Depressing Comic Week 9. [[FridgeHorror As in, the one where the kid talks to his dead father about what happened after, which is also by Kris.]]]]