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 (pictured above).
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.
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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.
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 Dreamfrom 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's lines when she barfs up the disc is also pretty sad.
The Great Bootleg:Dyingdyingdyingdeathdeathhelpbarfbarfbarfbarfbarfno one can stop the pain please can you stop the pain?
The Richscene 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 it's Claude Debussy's Clair de Lune
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His revelation at the second flex tape episode where he is actually a biggest fan of Phil Swift and was clearly heartbroken over his lack of recognition from Phil. Broken Pedestal moment.
from the Plug and Play Console episode. While it is a joke, he actually sounds sad.
