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8* In a way, his "CONKER IS TOTALLY BACK GUYS" video. He seemed like his hopes were genuinely crushed.
9* "There's no rest for a Jontron, is there?" from his ''The Zoo Race'' review. Funny scene of course, [[SugarWiki/HeReallyCanAct but the delivery is genuinely sad.]]
10* [[https://www.youtube.com/watch?v=3EVz3k3T3Ws His reaction to the game "Germ Killer"]] from the Plug and Play Console episode. While it is a joke, [[SugarWiki/HeReallyCanAct he actually sounds sad.]]
11** From the same episode, after playing the game "Boxing [[RougeAnglesOfSatin 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.
12* His reaction to Darth Vader destroying Jacques.
13---> "Oh no! He's just a boy! Oh, noooooooo! Oooooooohhhhhhhhhhhhhhhh!"
14* [[https://www.youtube.com/watch?v=FXPBSV0XC_8 "Apples and Breaks"]] can be a genuinely sad video, since it has Jon suffering a HeroicBSOD 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.
15-->"I'll miss you, Comrade."
16* At the start of [[https://www.youtube.com/watch?v=ghOKU8D-lMY "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:
17-->'''Jon:''' ...She was real to ''me''.
18** 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.
19* 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 [[Creator/{{Egoraptor}} "an old friend"]] and he [[WebVideo/GameGrumps "just wanted to play games with you like old times."]]
20** Earlier in the finale, after seeing that Creator/BeaArthur took part in ''Film/TheStarWarsHolidaySpecial'', he seemed genuinely distraught.
21* 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. TheReveal that Grimbo was AllJustADream [[AcidRefluxNightmare from a McDonald's induced food coma]] doesn't help.
22* Most of Bootleg!Jacques' dialogue in "Disney Bootlegs" is him bemoaning his existence...
23-->'''Bootleg!Jacques:''' [[AC:You will never know my suffering, forever trapped inside this robotic husk.]]
24** The Great Bootleg's lines when she barfs up the disc is also pretty sad.
25-->'''The Great Bootleg:''' '''Dyingdyingdyingdeathdeathhelpbarfbarfbarfbarfbarfno one can stop the pain please can you stop the pain?'''
26* The [[https://www.youtube.com/watch?v=tpiyKJ9zGks Rich]] [[BigLippedAlligatorMoment 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.[[labelnote:The said song]]it's Claude Debussy's Clair de Lune[[/labelnote]]
27* His revelation at the second flex tape episode where he's actually the biggest fan of Phil Swift and is clearly heartbroken over his lack of recognition from Phil. BrokenPedestal moment.
28* One of the ''The Most Shameless Dating Shows'' segments involves a clip from ''The Button''. It features a blindfolded date between a young man named Nathan and an anime fangirl called Sam. Nathan soon asks her for a hug, and once he gets it, presses the button to cancel the date. It's so sudden that even the Button tries to ask him why, with the unspoken reason implied to be that it was because the hug showed Nathan that she was overweight. Even more diabolical, this isn't the only time he uses this trick in the show to check for obesity.
29-->'''Jon:''' She needed a hug and looked what you did. Shit. Darn. Even the Button feels the pain, "Why, Nathan? Why? Why did you have to do it with such flair, style, and assassin-like accuracy?"

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