[[caption-width-right:305:[[TheWoobie Poor May]]]]

* "Momma's Little Ed". Eddy throws Edd out of his room, but Ed's PuppyDogEyes make Eddy change his mind.
* Everyone saying goodbye to [[ImaginaryFriend Jib]] in "Who Let the Ed In?".
* Rolf tearfully longing to go back to his old country in "Wish You Were Ed".
-->'''Edd:''' Rolf's frustrated, Eddy. How difficult it must be to adapt to a new way of life. To put aside handed down beliefs, and be pulled between two cultures.
-->'''Ed:''' [[CaptainObvious Rolf's homesick, Eddy.]]
** This is even sadder if you recall that Rolf is heavily based on series creator Antonucci himself, being the son of first-generation Italian immigrants, who had to learn to adapt to a whole new country and culture as a child.
* Eddy walking cold and alone in the ChristmasSpecial, which leads to a CrowningMomentOfHeartwarming as he walks up to a Christmas tree, notices a shorted-out light and replaces it with a light he's been holding the whole show, which causes the tree to shine like never before.
** "All I want is a good Christmas."
* May Kanker sobbing by herself in the closet because Ed was terrified and disgusted of her and her valentines day card, despite normally being the unflappable [[TheDitz Ditz]].
** Her sisters teasing her about the card she wanted to give to Ed, too.
* "A Fistful of Ed". [[TheWoobie Edd]] being sad because everyone believes him to be a bully. There's also the scene where Ed tells him that they can't be friends anymore and they both start crying. You even see Ed's heart literally ''break'' in that scene.
** The scene where Edd cries to himself alone in the science room. And after that, the scene where Jimmy witnesses Edd nurse a flower and makes it bloom, proving to him that he's not the monster he's being made out to be.
* "Take This Ed and Shove It" Had a bit of a depressing one where the Old Eddy starts breaking down after realizing he really is old and will never be a kid again, beating himself senseless with a Cane and then supposedly waking up as a kid and had only passed out when they were trying to get the jawbreakers, only to wake up again as an old man again and coming to terms that they are all old and he was only reliving his memories in his sleep. [[spoiler: And this was going to be the original ending to the series before it came back.]]
* "A Case of Ed". The scene where Edd is giving away his stuff because he thought he was dying.
** Heck the whole episode was sad, the nicest character on the show thought he was DYING. The fact that he trusted his friends only to find out they were joking is just insulting.
* In "Your Ed Only", when Sarah tearfully said, "I want my diary!" anybody would be upset over losing something so personal.
* It's very upsetting when Jimmy's belief in fairy tales and magical creatures gets crushed in "Tinker Ed". There's a particularly heartwrenching scene where Jimmy, in denial, tearfully reads a picture book about fairy tales in the library, constantly telling himself that they do exist.
* There's an episode where the Eds introduce Jimmy to a happy park called "Smileyville" (they even produce a map for him) in order to cheer him up. It apparently works, and Jimmy happily enters through the Smileyville gates, excited to take part in all the fun things the park has to offer (such as a teddy bear picnic). Upon entering, however, he discovers that Smileyville is no more than a dirty, disgusting alley. Fortunately, Rolf steps in to console the crying Jimmy and get back at Eddy for crushing his hopes.
* The episode ''Pick An Ed'' gets rather depressing concerning Eddy. He disguises himself as a new student named "Carl" in order to find out which of the other kids wrote something nasty about him on a wall. The other kids end up really liking this new persona though, and for the first time in his life, Eddy actually feels accepted. He enjoys it so much that he decides to stay as Carl forever. This becomes even sadder in hindsight after the movie, where we find out he secretly hates himself.
** There's one moment that's particularly sad. When Kevin first meets "Carl," he raises his hand up to him for a friendly fist-bump. [[HarsherInHindsight Eddy immediately flinches]].
* The other kids psychologically torturing Eddy into having a straight up '''panic attack''' in ''Smile For Ed.''
* Considering what little we know about the Eds' home lives, all three of them seem to suffer in some way. Ed probably has it the worse, since Sarah is constantly threatening to tell their mother on him (and it's implied that she often gets her way), and his dad seems apathetic to the whole thing at best ("AND DAD WILL JUST SIT THERE AND WATCH TV!"). Double D's parents communicate with their son through sticky notes, which could indicate that [[ParentalNeglect they're not at home much]]. And then there's Eddy's home situation [[spoiler: especially with his brother]]. If his parents off-screen appearances are anything to go by, they're overly strict at best and outright abusive at worst.
* [[http://static.fjcdn.com/pictures/Sad_37c879_701580.jpg This fanmade comic]], which depicts Eddy [[spoiler:tearfully saying goodbye to his buddies before moving out of the cul-de-sac]]. It's bad enough to see the lovable trio [[spoiler:part ways like that]], but it really hits hard for people who actually had to go through this with their friends.
'''WesternAnimation/EdEddNEddysBigPictureShow''' has enough scenes for its own page [[TearJerker/EdEddNEddysBigPictureShow here]].