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- Let's face it, Harry's entire character arc is a pretty much one long string of Tear Jerker moments. Let's see: he was injured by the Frightful Four when he was trying to protect MJ, later on he feels neglected by his father, who in early episodes of the series was stern and involved in evil activities yet showed concern for Harry when he was in danger, because he pays more attention to Spider-Man and also feels abandoned by Peter, believing that Pete only hanged out with him because he was rich after hearing mean-spirited comment from Nova. Later on he gets a symbiote and tries to be the new hero of the city, but he can't control it and quickly gets taken over by it and the only people who care about him are Peter and MJ, while his own father begins to ignore him and doesn't even care about him unlike in previous episodes, where Norman at least tried to talk with Harry, making Harry resent Norman and his rage increases while he is in Venom Form. Just as it seems that Harry is free from the symbiote, it turns out that a piece of it is still in him and Harry is once again under the symbiote's influence and going on a rampage. Furthermore, Harry is viciously attacked by Spidey's team, who don't know who's inside Venom symbiote and don't really care (granted they do find out and try to help him, but still) and attempt to destroy him and only Spider-Man genuinely tries to save him and free him from the symbiote, while Norman only shows interest in him when he finds out that Harry is Venom in order to manipulate him and only sees Harry as a weapon. Later on he and his father get attacked by Doc Ock and has to deal with the fact that other characters are (correctly) getting suspicious about Norman. In the season finale Harry sees his father, who has turned into a monster, and believes that it is all Spider-Man's fault and thinks that S.H.I.E.L.D doesn't care about his father and do not try to cure him, instead seeing him as just another supervillain to be taken down. The season one ends with Harry feeling betrayed by the rest of the world and his pleasant life destroyed. Harry becomes somewhat withdrawn from rest of the world and gives up on his father, while also becoming distant towards Peter. Later he has to deal with Carnage, who is actually Peter. Harry in his Venom from tries to kill Norman and sees himself as monster. Just when it seems that Goblin shows care for Harry by telling that his father would have been proud of him, he drops Harry from great height afterwards. Things don't get better, since in "Venom Bomb" Harry is still on bad terms with Spidey and still feels that no one is trying to cure Norman. But even after Norman is cured Harry is still bitter, as mentioned in an entry above. And his character arc hasn't ended, meaning that Harry will have more bad things happening to him in future episodes. If anyone deserves a happy ending in the series it's him.
- Gets worse. Things at first seem to get better for Harry in Season 4. His father's back with him, he seems to be on good terms with Spider-Man again, and even puts on armor to become a hero...just in time for Doc Ock to attach another symbiote to him (the Anti-Venom). Worse, this symbiote seems to be too strong for him to fight off alone. He not only at the end of the episode puts Flash in a coma (due to the symbiote being toxic to the venom one), Spider-Man has to shock Harry out of the symbiote to save him...only to land Harry in a coma himself. It's gotten to the point where Harry Osborn actually has worse luck than Peter Parker in this series, and considering Peter's usual luck in most of his adaptations, that's saying something.
- Seasons 3 and 4 have an overarching theme surrounding the The Chains of Commanding trope and how it's affecting Spider-Man. It's really difficult to watch Peter, who started the show of a happy go lucky teen who enjoyed life despite his hardships, slowly begin crumble under all the pressure everyone is putting on him. Only gets worse when Scarlett Spider uses his insecurities over this to manipulate him. Especially since Scarlett is the only one he talks to about his problems.
- Season 4 has one long running one that's easy to let slip your mind. In this season Miles gets trapped in the shows main universe by accident. Spidey takes it upon himself to look after Miles and vice versa. They become increasingly close and Peter developes into a cool, protective, brotherly figure towards Miles. The sad part? Miles will eventually return to his own universe. No matter what... Peter is going to loose someone he deeply cares about again, even if it isn't to death. Considering everything else he goes through this season this looming fact is just the depression cherry on top of the sadness sunday.
- This thankfully turns into a moment of heartwarming when Miles and his mother decide to go live in the shows main universe, with Peter.
- Like many versions of the character, this Spidey is something of a Doom Magnet, it's just not obvious at first. However if you add up all the people he's lost, nearly lost, or failed to save, it really starts to pile on after awhile. Not helped by the fact that it's clearly having a negative affect on him towards the end of season 4.
- Peter failing to get Uncle Ben's cake for his remembrance, after fighting for his life against the Frightful Four at Midtown High.
- A brief one in "Venom". Nova tells Peter that the team are friends with him now, so he doesn't have to suck up to rich-kid Harry to have a pal... right as Harry had walked up to the table. By both the way Harry stormed off and Peter's reaction, it's likely Harry has wondered if his money's why Peter stays around, and Peter's his best friend so he probably knows Harry might have thought about it too.
- Ava's backstory, and the flashback to Uncle Ben being killed.
- Spidey trying again to reason with Conners/Lizard near the end of "The Sinister Six". Rarely have Spidey's puppy-dog-eyes been so moving.
- Harry and the Green Goblin meeting. Harry's become Venom, and he's attacking and trying to kill his father in a blind rage. When Peter tries to talk him out of it, the sheer resignation in his voice is just heartbreaking.
- Harry: He's a monster...I'm a monster...
- The Green Goblin telling Harry in his father's voice that his father would have been proud of him. And then attempts to kill him while laughing gleefully.
- After barely defeating the Green Goblin and Venom with the last of the power in his Iron Spider armor, Spider-Man fails to stop the self destruct sequence of the Tricarrier, and just gives up, presumably accepting death. Thankfully Nick Fury was able to stop the countdown at the last second, but seeing our hero ready to die after giving it his all is heart-wrenching.
- The second meeting between Spider-Man and Harry in "Venom Bomb"'. Spidey is able to deliver some good news: Norman is back to normal. The rest of the meeting, however, is rather somber. Harry is unable to see his dad and seems resigned of that not happening, despite Spider-Man's promise that Harry will be able to see him soon. Harry also bitterly mentions how "everything's changed now", implying that things will never go back to the somewhat more pleasant times they were before.
- In "Second Chance Hero", Harry was willing to let himself die in a elevator crash after all the crap he's had to put up with in his life. What makes the scene more tragic is that Spider-Man, unknowingly to him his best friend Peter in disguise, is left to unsuccessfully convince Harry to rethink his decision. Even though Spider-Man is blamed for ruining his life, Peter is still determined to prove himself to Harry that he will always be there for him through thick and thin.
- Power Man's backstory, while not true to his comic's origin is still very tragic.
- Spider-Man failing to save Curt Conners/The Lizard again at the end of "Stan By Me". When we're given a glimmer of hope of Conners being returned to his normal self, the problem is actually made worse. The machine meant to correct Conners' brain waves and return his human consciousness instead strengthens his Lizard side, completely suppressing his humanity. Having succumbed to his monstrous state, Conners escapes into the sewers yet again with unknown intentions.
- Norman Osborn of all people evokes this in the Season 2 finale. He truly was disgusted by his deplorable actions throughout the show and wanted to change for the better and help people. But, Doc Ock forcibly changes him back into the Green Goblin, and now he's more Goblin than human so Dr. Connors can't help him for now. It's a tragedy.
- His screaming in protest as Doc Ock injects him with the new goblin formula doesn't help.
- "Ultimate Deadpool" was perhaps the show's funniest episode ever. Deadpool's real (or rather, most believable) Origin Story, on the other hand...well, let's just say it's classic Deadpool: once you get past all the laughs, it gets so sad you just want to hug him
- "Ultimate" has Spider-Man being forced to fight his friends as they (in the Goblin mind set) attack him physically and mentally with mind games. With him telling them to try and fight it!
- Flash Thompson's heartfelt speech to Spider-Man about finally become a hero like him, and the difficult life he had to live.
- While their backstories aren't delved into much, Cloak and Dagger still seemed very sympathetic.
- This incarnation of the Vulture will bring a tear to your eye.
- The very existence of Miles Morales in an alternate continuity, since in that continuity Peter Parker died "saving the world".
- Despite the fact that Miles is thirteen, only recently got his powers, and fights villains that are "scarier" than canon Peter's, he blames himself for Bystander Syndrome in letting Peter die. When he sees his Goblin about to crush canon Peter, he whispers, "Never again" and pulls out an epic Heroic Second Wind.
- In quite possibly the most chilling scene in the show thus far, the episode "The Revenge of Arnim Zola" has the titular antagonist almost succeeding in putting his consciousness in Spider-Man's body and erasing the wall-crawler's soul. Made even worse by watching Spidey literally fighting for his life as he's fading from existence.
- Arnim Zola: *calmly* Shhhhh...it is almost over now, Spider-Man.
- Surprisingly enough, the Collector is pretty sympathetic throughout the "Contest of Champions" arc. It's hard watching him being constantly insulted and put down by the Grandmaster.
- The season starts with Peter's "Parker Luck" kicking in. Sure it gets better but watching him go from such a high point to such a low one can be at least a little upsetting given how much he's been through to get to that high point.
- What little we see of Scarlet Spider's backstory in the season opener is this, and only seems to get worse as the season goes on.
- Miles getting trapped in the show's main universe, and away from his mom, AND with his archenemy.
- Vulture finally realizes that he's being used as a pawn, only to have his free will taken from him moments later.
- We get to see just how deeply ingrained Scarlet Spider's trust issues are in "Double Agent Venom."
- The reason Rhino betrayed the team in the last episode? He just want to be a normal kid again.
- Sandman and Iron Spider's heart-to-heart in "Beached." They just want others to treat them normally and want others to want to hang out with them.
- There's also Sandman's entire situation in this episode.
- More "Parker Luck" hits really hard in Anti Venom Due to the events of the episode Flash is in a coma and his friendly symbiote appears to be dead due to Anti-Venom purging it. Meanwhile Harry was the one the Anti-Venom symbiote possessed, and the only way to save him was to shock him, and that lead to him also being in a coma. By the end not only does Norman blaim Spidey for what's happened, but so does Peter himself.
- To make it worse it's impossible to tel if either Flash or Harry will recover.
- This episode makes it clear that Flash is sensitive about his standing in Peter's eyes. Given that it was Peter, both in and out of the mask, that helped Flash become a better person despite their rough history together in their civilian identities, and that he's been a Spidey fanboy from the start it can be really hard to watch Flash's insecurities over it come to the surface.
- As with any episode that talks about Scarlet Spider's past Forces of Nature has a bit of this.
- After the events of "Anti-Venom", Flash is okay, but is stuck in a wheelchair. He's dissapointed when he's benched from the mission, but does his best to protect Aunt May. However, he is once again injured and it's unknown what happened to him when May was captured trying to get him to safety.
- It's still unknown what became of Harry Osborn.
- "The New Sinister 6: Part 1" is a Wham Episode that has a Downer Ending as, true to form, Peter's luck gets worse: Rhino was brainwashed and wasn't the mole, after all—it was the Scarlet Spider, whose animosity towards Doctor Octopus was faked and was really in league with Ock all along, betraying Spider-Man and unmasking him to Ock. The fact that the man who he learned to trust has stabbed him in the back even drives Peter himself to tears.
- Speaking of Rhino, it's all but implied that Rhino is forever lost to Doc Ock, considering what Ock used to brainwash Vulture and take away his free will.
- Both Flash and Peter especially feel betrayed by what Scarlet Spider did. Flash is downright angry and Peter's just heartbroken.
- When the Parker house is crushed, May thinks Peter's been killed. Her cry out is heartbreaking The relief she feels when she finds out he's alive is both Heartwarming and Tearjerking.
- Turns out Scarlet Spider really did have a Dark and Troubled Past. He was just a lonely street kid with nothing. He feels he owes Ock for "rescuing him". However, this is misplaced as it's revealed like with Rhino and Vulture, Ben was being used too. Then after his Heel Realization...
- The ending of The New Sinister Six: Part 2 When Ock is finally able to kill Peter and May, Ben has a Heel–Face Turn and saves them. However, HYDRA island is destroyed and is ready to crash into New York. Ben gets Peter and May to safety before making a Heroic Sacrifice by retorting the island and plunging it into the ocean, presumably killing him.
- Ben's last words to Peter: "Your compassion isn't your greatest weakness. It's your greatest strength. Keep being a hero, punk."
- Peter's reaction to his death. He keeps searching for what seems like hours. Finally, Cho tells him that he's gone. Peter's heartbreak is evident in that scene.
- Not only Peter, but Cho and Miles attempt to rescue and search for him as well with no results and seem just as heartbroken.
- Just in general, things are just so bad for Spidey after this point—New York has been saved, but Ock pretty much won in costing him three fellow heroes (one who's sidelined, one who's in a coma, and the last who seemingly sacrificed himself), and knows his secret identity.
- In the second part of "The Symbiote Saga", Harry goes to sacrifice himself to stop Carnage from taking over New York. Peter's reaction is heartbreaking. He begs the Symbiote to take him instead, but it doesn't, leaving him to face the fact Harry's the only one who can use the Symbiote to stop Carnage. This is even more heartbreaking if you remember what happened to Ben earlier; now seeing his best friend about to die the same way causes him to nearly break down. Lucky for both of them, Harry comes out okay.
- Then in the third part of "The Symbiote Saga", after Mary Jane is freed from the Carnage symbionte, she faints, but Peter, Harry and Flash assume she died, Peter even cries, thankfully she recovers.
- In the second part of "Return to the Spider-Verse", Web-Slinger's universe is one of the only known ones where his Uncle Ben is still alive. It was heartwrenching for the main Peter Parker to leave this dimension behind, and seeing that universe's Uncle Ben alive reminds him of what he lost.
- The way the scene in general plays out. The fragment opens a portal to the next universe and Miles is about to go through only to notice that Peter isn't following him. No, instead he's watching his alternate self conversing happily with Uncle Ben. It's only after Miles talks to Peter a bit that they actually leave, and as Peter talks... he just sounds kind of tired.
- To make it even more impactful on the viewer Miles has to snap him out of it by putting a hand on Peter's shoulder. The scene in general really brings home the fact that everything Peter is revolves around his Uncle's death, and emphasizes his role as a Sad Clown.
Peter: I just wanted to take one last look at a world where Uncle Ben was still alive.
- Noir lost his Mary Jane in building collapse that he blames Joe Fixit for. It's not enough that Noir was already sad and dreary enough but just when things seemed to be going his way the love of his life is taken away by doing the one thing that could get her kill just for the sake of saving a few civilians.
- Peter very nearly looses Miles in this episode. He's clearly shaken up by it for a moment before he reminds himself that he can still save him.
- Part Two of "The Spider-Slayer Triology" reveals that Ben Riley is a synthozoid. He doesn't take it well.
Marvel Universe (Comics Based On The Show)
- In the story "And Sometimes You Get What You Needed", Spider-Man saves a mail worker from a thug. As a "thank you", she introduces Spider-Man to a entire room filled with letters and gifts to Spider-Man from his fans and the people saved in the past year. One letter happened to be from Aunt May, who watched the Frightful Four attack Peter's school (from the first episode) on television. She was worried she would lose Peter the same way she lost her husband, Ben, until Spider-Man saved Peter and the students from certain death. The letter ends with her quoting Uncle Ben's famous words "With great power, comes great responsibility". This shows that no matter how many people hate Spider-Man, he will always be an inspiration for many and appreciated for his acts of heroism.
- The first story of issue seven, we end on an incredibly somber note when we find out that the monsters Spidey and Power Man were fighting where a manifestation of a deceased horror host, Adrian Chase, who's spirit came to say goodbye to his son, Trevor. The way the panels are presented are beautiful and set a cold atmosphere for a rather dark and depressing end to otherwise light-hearted series.