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Tear Jerker: The Order of the Stick
The Order of the Stick might be the only comic in existence that can have some hilarious meta/Fourth Wall jokes (and a couple of Lampshadings) and then successfully pull off a heart-wrenching death scenein the same page.
Note: Please keep the examples sorted in chronological order, as to avoid repeats.
Also here, with Haley battling with her own sense of self loathing as the countdown comes for Southern Continent New Year, debating whether to risk kissing Elan, and by the time she hesitantly reaches out to him, some random Azurite has already grabbed him. The last line of the strip is in her (at the time) custom cryptogram, but says, "happy new year."
Eric: Hi Roy! wanna play blocks with me? Roy:(a tear running down his face) More than anything.
Then you find out that they made the block castle 34 times without Roy noticing because he was enjoying it THAT much.
At first, this strip just looks like a gag involving Roy being frustrated as he tries to communicate with Haley. But then you think about it, and about how normal she treats the whole scenario, and you realize that for months, she's been fighting and struggling on her own, and keeping herself going by talking to all that remains of her former leader and friend, because she cares about him that much, misses him that much, and needs him that badly. It's kind of sweet and kind of horribly sad.
Vaarsuvius keeping the soul splice and leaving his/her family behind to try and fix everything else.
Or just before It's a memory of her invisible and unable to cast spells, as she bumped into terrified, fleeing soldiers on the way to the ship. She was forced to watch as they pleaded for her help before getting torn apart by the horde of Hobgoblins...
MITD: Wait, Mr. Stiffly! Come back! Mr. Stiffly! MR. STIFFLY! O-CHUL!
When O-Chul escapes, he takes out Redcloak's right eye. As punishment for his failure, Xykon forbids him from using Regenerate to restore his eye. So now he's got an eyepatch over his right eye and one working, left eye. In one comic, just before he gives a big speech, he is seen looking in a mirror. His reflection shows his face reversed, so he sees Right-Eye. His brother. And it dawns on you that that's who he'll see every time he looks at his own reflection. He just stands there looking at the mirror for a panel or two, and says, simply, "It'll all be worth it. You'll see."
"Enor...don't you see? It has to be you. It has to be. You have the Victory String." Remember that 6 strips prior to this, Gannji had given him the very same string so Enor would have the bravery to face his opponent. Little did either of them know that they would face each other.
And a little while later, it's revealed that even Belkar, the Order's Token Evil Teammate, was affected by it. Specifically, he released the arena's previously-featured dinosaur to disrupt the fight (which allowed Enor and Gannji to escape) because he heard Roy say that watching the two fight was like watching someone be forced to duel his own puppy. Cue Belkar's point of view, where he sees Enor's face replaced by Mr. Scruffy's head and his own head replacing Gannji's.
"No! Stop! You don't have to do this, little ones! He just wants you to think you have to! You can- AAAGH!!- You can fight back! Resist! No! NO!! Don't you- AAAGH!!- Don't you understand? I love you all! I love you! Why don't... you love... me?"
Then a couple of comics later when Xykon's rounding up Team Evil to go after the next Gate he casually asks where "what's her name, the chick with the pig tails" is. No matter how colossally misguided it was, she did love him, and it's a little heart-wrenching to realize how little he thought of her.
And when the rest of Team Evil finds out what happened to her, the only one actually upset about it is the Monster in the Darkness. When one of the Demon Roaches asks him why he's upset, he explains how sad it is that Tsukiko really just wanted to be loved.
Demon Roach: So what? Who cares?
MitD: Exactly. That's why I'm sad.
It's also possibly a bit of the You Bastard to people who disliked her "thinks she's in a romance novel" character.
While Elan is trying to figure out how to feel about his father:
Elan: I thought it was tough to figure out how to feel about Nale, you know?
Roy: I think you're overemphasizing the importance of biological ties, Elan. Nale has tried to kill you three times!
Elan: I know that! But sometimes when I was little, I would walk in on my Mom crying about having lost a nail. And now, I don't think she was upset about missing hardware at all!
The consequences of the Familicide spell Dark Vaarsuvius used finally catch up with the Order: "The propensity of both dragons and humans to breed outside their species is well documented." The entire Draketooth family was related to a Black Dragon.Which will now prevent the Order of the Stick from directly finding the Gate. Even worse than that, Familicide did not only kill the Draketooths. It killed anyone that was related to them by blood. And the Draketooths happened to be scoundrels who propagated by seducing random bystanders and absconding with the resulting children. All those bystanders are now dead - along with every living member of their families! And there is no reason to believe that they're an isolated case. What really sells it is V's expression. The Order may forgive him/her, but s/he never will.
And throughout V's explanation of why Familicide was so awful, we see a montage of several bystanders and their families being slain by it.
When's the last time we ever saw V cry? Not when his/her mate was threatened, not when s/he was served divorce papers, not when s/he saw his/her children's legs broken, house burned down and mate crucified on a tree. This hit him/her hard.
Failing her save against a Holy Word, Sabine apologizes to Nale and gives him some last advice, along with "I love you... forever." However, Nale was deafened by the same attack and can't hear her, so he doesn't understand what's happening.
Even sadder since these are the last words she says to him while he's alive... and he can't hear them.
While it's outside of the strip, Rich's injured hand and the responses people have given wishing him well.
Mr. Scruffy's useless attempts to stop Malack from killing/vamping Belkar.
On a related note, Malack's desperate attempt to preserve his friendship and form a truce with Durkon, only to get rebuffed primarily because of his vampirism.
Made either better or worse by the fact that he died happy, because it meant he was finally going home.
As a vampire.
What make it especially sad is that he died mainly because he refused to compromise and he put his faith in the wrong people: Malack who betrayed him but was willing to walk away and Thor who he worships wholeheartedly but who wasn't even paying attention when he died.
In the aftermath of that, Belkar trying to rush off and warn the others, only to get vertigo due to his injuries. So he starts crawling.
His shocked disbelief that he is still alive while Durkon is turned into a vampire. Deep down it really seems like he thinks his life is worth less than Durkon's.
Before his fight with Malack, Belkar said that he had something to live for, which is why he will survive. Durkon's last wish before he died was for Malack to not harm his friends because they have more to live for than him.
Remember the old example that out of 800 strips, only one had no jokes? As of this posting, there are over 900 comics, and there is a second strip with no joke. It's Durkon's death, and him saying that he's going home.
Right afterwards: Belkar, barely alive, crawling back to the rest of the Order and breaking the news — and Roy almost attacking him, thinking it was another one of his tasteless jokes.
Made worse on Belkar's side by the fact that Roy only comes around to believing him when Haley points out that She doesn't think he COULD make up a story of heroic sacrifice. Harsh.
Made worse if you believe that Roy's anger isn't due to it being, well, Belkar, but due to his desperate attempt to deny what has happened to his best friend.
As it is the first comic in which Durkon is absent ever since he showed up to save Belkar, it will also be the first one that will make you cry seeing the joint "Thanks, everyone" message from Roy, Haley, Elan and Durkon at the very end of the page (if it didn't start happening at the latter's actual death, that is).
"He just walked in there and saved my life and got straight up murdered for it." Talk about tearjerkers...
Qarr taunting Vaarsuvius with the horrific consequences of his Familicide. V is curled up in a ball sobbing when Qarr calls him "history's worst mass murderer". Blackwing isn't any help either since the only rebuttal he gives is that "history isn't over yet", which means that Blackwing technically agrees with Qarr.
From the same comic, Vaarsuvius casually mentioning that "Master Thundershield" should have Raised one of the Draketooths by now. Cringe-inducing since we know how sad V will be when (s)he finds out about Durkon. (S)He may even go through another Heroic BSOD if it occurs to hir that it might not have happened had the Draketooths still been alive when the Order & the LG arrived at the pyramid, or if (s)he had been present for Durkon's fight with Malak.
It's clear from #885 that Roy is really guilt-tripping over Durkon's death.
#887. Everything has gone wrong. Durkon's dead, V is lost, Tarquin and Nale are winning, and Xykon is on his way. The Order is surrounded on all sides, and there's no where left to run except unknowingly into a happy ending created by an illusion.
The happy ending illusion itself. First, long-dead secondary characters are alive and well in it due to the Order members not knowing that they're dead. Second, it's pretty obvious that the person (or someone if it's collective) whose illusion is shown would have preferred Durkon to be alive and Belkar to be dead rather than the other way around.
Everybody under the spell gets their happy ending. Haley is shown rolling in gold and helping her father take over the Thieves' Guild, which Roy wouldn't know anything about. Elan makes peace with his family, something the other two don't see as a happy ending. Roy gets to rub his swords-are-better-than-magic philosophy in his sister's face, something the other two wouldn't know would be a part of his happy ending. Clearly, there is no one point of view; everybody under the spell gets their happy ending. Belkar is dead, and is presumably killing monsters in the abyss. That's his happy ending.
And his cat's dead too. Which means either one of his teammates found the cat too evil to keep around, or Belkar wants the only thing in the world he cares about to stay by his side.
At Belkar's funeral, Roy and Varsuuvius are walking away. They don't care enough even to stay as long as Elan has.
What's even worse; NONE OF THIS CAN EVER HAPPEN!!! It's been shown multiple times in the comic that the Unspoken Plan Guarantee is almost a law of nature. The only plans that have a chance of happening, are the ones the audience doesn't know about until it's too late. This spell means none of what we see has a chance of happening. They won't be able to hold Redcloak down so Roy can fight Xykon. Roy won't be able to use the special move his grandfather taught him which had, until now, remained unspoken. They can't throw Xykon's phylactery into the ocean/lava. And Elan won't get his dinosaur ride.
#923 came out. Elan got his dinosaur ride so there me be hope for this yet.
In #888 is somehow both tearjerking and hilarious, as we see that Elan thinks it might be a good thing if his parents got back together... the imagery and dialogue are just hilarious, but the implications make you want to cry.
In #889, Elan breaks the party out of the illusion by admitting the truth that he's been hiding from. He can never fix his family, his dad and brother are irredeemable. His dream of his family being together again will never happen.
A small, but very gut-wrenching, one as Roy sees the vampire Durkon for the first time.
Another gut-punch as the newly freed from thralldom Durkon goes to heal Roy like he usually would in a situation like that... and ends up hurting him instead. Ouch.
Small, and short, but Nale is horrified, angered, and hurt when Vampire Durkon just casually gives Zz'dtri a Neck Snap. Mind you, the two were actually friends.
In #913, Elan's reaction when he sees his father Tarquin kill his brother Nale.
Nale's monologue right before Tarquin stabs him to death. He only wanted to be free from his father's shadow.
You don't notice it at first due to his professionalism, but Tarquin takes a moment to confirm Nale's motives before resigning himself to killing Nale to avenge Malack. In fact, Tarquin explained to Nale that the arc was his chance to prove himself. Tarquin didn't want to go through with it, but he couldn't ignore Malack's death.
Can also be read as Tarquin realising that Nale will never be his pawn and no longer holds any use for him. It doesn't really matter what interpretation you choose, both are definite tear jerkers.
Tarquin made a Freudian slip when told by Nale that his father and Malack were going to kill him anyway. In #849, Tarquin reassures Malack by telling him to look forward to the end of the mission. He was going to off Nale.
#914 confirms the latter, as Tarquin goes on about how Nale was just a B-class villain and that Elan had outgrown him. Tarquin's indifference to killing his own son makes it even more of a tear jerker.
To add to that, Tarquin saying that Elan would be the only one who didn't desire Nale's death... Cue the last panel showing a very pissed off Sabine who just witnessed her lover's death through the IFCC's TV set and destroyed it in a fit of rage.
Sabine:(to V's soul as it returns to his/her body) Knock 'em dead, elf.
Reread "Happy Ending" and "Dream Wedding" knowing all this will happen.
As Nale's ashes scatter in the wind, Elan grasps hopelessly at them, begging for his brother to come back.