- In a way, his "CONKER IS TOTALLY BACK GUYS" video. He seemed like his hopes were genuinely crushed.
- This part of one of Jon's livestreams with DidYouKnowGaming. To basically explain what happened, Jon and DYKG were playing Super Mario World and reading livestream questions. It seemed all and good as Jon beat one of the castles....until he read the question "Are you still friends with Arin?". Jon automatically looked upset and even looked like he was going to say something, but stopped himself. He didn't answer the question and simply did 'hummed' along to the music after he beat the castle. And then he shrugged it off once he read a joking question. Even DYKG looked a bit concerned when Jon remained silent, giving fans the impression that something may have happened between him and Arin after he left Game Grumps. Granted this was Jossed later on when Jon and Arin met up at MAGFest (Also the two were seen not just interacting after the convention, but Arin confirmed beforehand on a Q&A with Ross that he and Jon were still on good terms), but it still gave an uncomfortable vibe that Jon and Arin weren't friends.
- The Twitter meltdown that almost lead to him and Austin Hargrave, better known as co-creator of Normal Boots PeanutButterGamer, to stop being friends. Without going into details, some disputes lead to Jon and Austin delivering some very hateful replies which lead fans to worry if the two were really done being friends. It goes into heartwarming mode when Austin apologized to everyone on Twitter and Jon, which lead to Jon telling him all was water under the bridge and they should go out for a drink next time.
- "There's no rest for a Jontron, is there?" from his The Zoo Race review. Funny scene of course, but the delivery is genuinely sad.
- His reaction to the game "Germ Killer" from the Plug and Play Console episode. While it is a joke, he actually sounds sad.
- From the same episode, after playing the game "Boxing Werstle", he cracks a joke about the game's misspelled title ("This is the werstle game I've ever played!") and smiles. However, a few seconds later, this ends up fading into a genuinely sad-looking expression.
- His reaction to Darth Vader destroying Jacques.
- "Oh no! He's just a boy! Oh, noooooooo! Oooooooohhhhhhhhhhhhhhhh!"
- "Apples and Breaks" can be a genuinely sad video, since it has Jon suffering a Heroic BSoD and in tears over accidentally breaking his Nintendo DS screen. The tribute to the DS at the end with the Scorpions' "Wind of Change" playing is especially plaintive."I'll miss you, Comrade."
- At the start of "Titanic: The Legend Goes On", Jon gives a monologue of his girlfriend who he lost in the Titanic disaster. When he comes across the titular film, which claimed to be an adaptation of the "legend" of the Titanic, Jon states that if the Titanic is merely a legend, then that means it never existed, and therefore his girlfriend never existed. We then see a flashback of Jon at a restaurant with the rather confused waiter asking why he ordered two meals and only ate one, and we see that no one's sitting across from Jon. What really drives it home is this line:Jon: ...She was real to me.
- While it's a joking overreaction to Titanic's singing mice appearing again, Jon putting a gun to his head and muttering pleas for it to work is kind of distressing.
- In the Starcade Finale, Jon wants to know who has been playing Darth Vader all along, and why he's been forcing Jon through all of this. His answer? Because he's "an old friend." and he "just wanted to play games with you like old times."
- Jon's house goblin Grimbo from the Food Games two parter. The poor creature is kept chained to the couch and hates Jon enough to try to put a magic curse on him. In part 2, he drinks enough Pepsi to kill himself. The Reveal that Grimbo was All Just a Dream from a McDonald's induced food coma doesn't help.
- Most of Bootleg!Jacques' dialogue in "Disney Bootlegs" is him bemoaning his existence...Bootleg!Jacques: You will never know my suffering, forever trapped inside this robotic husk.
The Great Bootleg: Dyingdyingdyingdeathdeathhelpbarfbarfbarfbarfbarfno one can stop the pain please can you stop the pain?
- The Great Bootleg's lines when she barfs up the disc is also pretty sad.
- The Rich scene in "Dark Dungeons", where a random man named Rich appears in Jon's house. The sad part isn't until the end, where Rich sadly looks back at Jon as he's halfway through the door with a look of rejection on his face as sad piano plays in the background.The said song
Tear Jerker / JonTron