Season One
- "The Beauty Contest", with the reveal Vicious Oscar used to be a famous tv star. Everything changed when, while being a beauty contest juror, he mistakenly gave the first place to Jerry, when Roy previously bribed him to make Mimmi win. It's not shown what Roy did to him, but it was bad enough to make him into the mentally damaged hobo we all know.
- "My Friend is an Ant", really beats the crap out of Jerry. He wins a contest by bringing his favorite ant, only to realize it will get dissected for the museum. His plans to get it back fail, ending with him crying alone in his room. There's a brief Hope Spot when the ant breaks free from its cage to reunite with its beloved owner.....only for Jerry to accidentally squash it in his sleep. Anyone who has ever lost a pet can DEFINITELY relate.
- And perhaps what stings the most was just how close the ant was to salvation...
- When he realizes that the museum means to dissect the ant, he tries to take it back, only to be run over by a car and his ant to be taken away. Not only he's in pain, but the fact that almost everyone just flatly ignores (with the teacher even berating him for not paying attention to the adults) it just goes to show how freaking cold and mean this series was.
- What makes this harsher is that Jerry was having a nightmare of the ant getting dissected. He wakes up screaming for his pet, goes back to sleep and hears a small squashing sound. The look of stunned disbelief on his face is almost painful to watch. And then the episode ends.
- The end of Frank in "Neat and Tidy", when he is driven insane, tied-up and taken to a dog pound because Jerry, Thomas and Eric thought he had rabies. Made even worse when you remember how he even got into the mess; all he wanted was to be clean for a day.
- Mimmi celebrating her birthdays alone in "The Delivery" because her parents were more focused on themselves than their daughter.
- Jerry's treatment throughout "Jerry's Lucky Day".
- Despite what a royal Jerkass he is, Frank getting trapped in the meat fridge in "Supermarket" is quite sad to see. Especially cruel when his friends (who are completely unaware of what happened to him) push him off a slope, resulting in him getting trapped in an ice cream truck, while Frank lets a Little "No", because that's all he can do.
- Frank failing to get head lice in "Head Lice" because of his buzzcut. Normally, he would be angry or beat the shit out of Jerry because his plan to get head lice didn't work on him. Instead, he just sadly says "You said it would work!", showing how trusting Frank was this time.
- In "Country Cousin", after going through great lengths to get crowned to get Linda's attention, Thomas and Eric tell the class about the callous way he treated Simon because Frank didn't keep his promise to let them dance with Linda. It results in Frank losing the contest and getting booed by the whole class. While he's moping alone, he's approached by Simon, who says he forgives him for all he's done and would rather spend time with him. Frank is nearly moved to tears by this.
Season Two
- While "Christmas Party" is Played for Laughs as Oscar ruins the town's Christmas party, and gets away with it, it's not much the antics of a mentally damaged man, but pent up outrage at a town who did nothing to help him as he devolved from a beloved tv star to a crazy hobo.
- And then he frames Jerry for the missing gifts. Poor kid can't have a break!
- While it's hinted the old Oscar is still in there somewhere (such as remembering his friendship with a con artist in "Miracle Cream"), what everyone sees now doesn't appear to remember anything about himself at all. Think how his brother might feel...
- The whole subject of "TV Gossip" is pretty heavy. It's about Jerry's dad getting framed on television due to a smarmy tv show taking out of context some comments made by the Three Friends and Jerry for the sake of drama. Things escalate to the point all teachers get arrested because the reporters choose to believe in the kids' flimsy lies. Thankfully it's all resolved by the end.
- Jerry's mother suffering through the episode after her husband is arrested.
- Jerry tries to ask the teacher for help to release his dad, even breaking down in tears. Only for her to be apathetic and tell him to "tell his troubles to the psychologist instead".
- Tess in all off "Pen Pal." The Three Friends and Jerry wrote letters to her pretending to be a pen pal they made up named "The Lone Romantic". They eventually invited her to a date only to stood her up and mock her as she waits all night for her new friend only to leave in tears.
- It's clear that Jerry was really uncomfortable taking part in the prank, but went along with it because he wanted the approval of the Three Friends. Who proceed to take advantage of him as usual.
- Jerry breaking down crying after the death of the robot dog in "Stray Dog".
Season Three
- Jerry becoming Hated by All through the series. During the first episodes, the Three Friends were in cordial terms with Jerry and willingly hanged out with him. But after three seasons of Jerry's zany schemes failing and getting them into trouble, it's clear the Three Friends want nothing to do with him. In fact, they want him gone. Most episodes end with him getting beaten, humilliated, sometimes for things that he didn't even do. All he wanted was to have friends, dammit!
- Eric being among those people stings considering he was the only one of the Three Friends who showed some sympathy to Jerry. Now he gleefully joins Frank in treating him like crap.
- How devastated Frank is when Linda (who's infatuated with a super model) calls him ugly in "Miracle Cream". We've never seen him so depressed before, and when he stomps at a puddle showing his reflection screaming "UGLY!" shows how saddened he is about the whole thing. You really do have to feel bad for him. Heck, Jerry even places a reassuring hand and tries to help him.
- In "Our Son is an Ostrich", Thomas confides to his friends about his fascination for ostriches, only for them to mock him for it. What makes this worse is that his parents don't support his hobby, seeing it as a freaky obsession. And then he's attacked by an ostrich, sending him to the hospital for a week.
- Thomas breaking down in tears as he realizes why his parents never visited him when he was hospitalized is gut wrenching, and he's so heartbroken that he completely abandons his love for ostriches.
- The Three Friends sabotaging the cake in "Record Cake" because they can't stand seeing Jerry happy for once.
- While it's all Played for Laughs, the events of "The Move" are this. Jerry finally finds a group of friends who treat him nicely—inviting him to play, welcoming him with respect, and wanting to make him their leader—and Jerry doesn't trust them. The Three Friends have abused him and betrayed him so many times that now he just can't accept that someone ever treat him kindly without an ulterior motive.
- Poor Jerry's mother is treated like crap by her husband through the episode.
- The way Mrs. Bertwhistle is treated throughout "Swimming Teacher".
