History EpicFail / TheRunawayGuys

** Jon's HumiliationConga in the Yoshi's Tropical Island board. [[https://www.youtube.com/watch?v=RcGgA2OnsV0&feature=relmfu You know the one.]]

** In Episode 7, while trying to enter Tim in so he can choose a character, they crash the Wii. No, not the game, ''the entire system.''

** LetsPlay/JoshJepson's fight with LetsPlay/AttackingTucans. Tucans has never played the game before, and then picks Link as his character, who Josh says isn't a good fighter in 64. In a ForegoneConclusion, [[spoiler:...Tucans beats Josh without losing a life, and thanks to picking up a healing item at the end, with ZERO PERCENT DAMAGE]].

-->'''Jon:''' Oh. I didn't think that through.

** It takes ''three tries'' to get Toadette's Music Room to work. The first two attempts result in the game crashing to the menu from communication errors. It happens ''again'' in DK's Stone Statue, with the added bonus that they have to change capture cards, followed by ''more'' fiddling to get the colors to work out.

** It takes ''three tries'' to get Toadette's Music Room to work. The first two attempts result in the game crashing to the menu from communication errors.

** Emile decided to give him an advantage against Jon by playing as a bonus character, the final boss of the game, with overpowered stats across the board. Meanwhile, Jon played as a regular character. Emile's points scored on Jon: 0.

* From ''VideoGame/MarioParty'':

** [[https://www.youtube.com/watch?v=IKZ0bYO3NNo The Bonus Episode]]. Tim's quest to fight and unlock Jigglypuff. [[UpToEleven It has to be seen to be believed.]]

** Peach on Pagoda Peak lands on duel spaces four times. Every time, she duels Jon, including once when he had no stars and four coins (she got two coins out of this). Later, this leads to her giving Jon his star back.

** Episode 1 has Chugga die to the first boss.
*** On the first hit less than 10 seconds into the fight, no less.

** Nobody was really playing well in "Super Mario Bros," but Jon deserves special mention for throwing away a good shot at winning by dumping his money into easily avoidable properties where he had no stocks, eventually forcing him to [[spoiler: auction off his shops, one by one, including TWO monopolies, and nearly go bankrupt.]]

** In the last episode, Jon tries to show off the 1-Up trick in 1-2 by bouncing off a shell in a single-wide space. He only manages a few bounces before the shell hits and kills him. Chuggaa then does the shell trick perfectly, which Jon predicted immediately before.

--->'''Jon:''' '''GAAAAAAAAAMMMMEE!'''

--->'''Jon:''' I think we just pulled a LetsPlay/FreelanceAstronauts.

--->'''Emile:''' '''OH MY BARK!'''

--->'''Jon:''' ...What just ''happened''? I groundpounded and it kept bouncing, Wario was humping the ''sky'', and I don't even ''remember'' what happened to Tim...

--> '''Tim:''' ''D'oh, I missed!''

*** [[spoiler:Only for the Barter Box he got from the Item Space after said Star to be stolen by Jon using his "''insurance policy''" Plunder Chest to payback him for the stolen Koopa Kard.]]
--->'''Emile:''' '''OH FRICK!!'''

---> ''I'm just gonna sit here and wait for the word to fill itself out.''

*** Now animated as, fittingly, Between A Rock and a Hard Place.

*** This really burns Emile in his LP with MasaeAnela; had she set the Snifit Patrol earlier Emile wouldn't have lost his coins. Why? [[spoiler:He was one space in front of Baby Bowser.]]

** Doubles as a CrowningMomentOfFunny, but Episode 15 amounts to over twenty minutes of them failling to infiltrate Hyrule Castle and getting thrown in jail. ''Sixteen times.''

** In the last episode, Jon tries to show off the 1-Up trick in 1-2 by bouncing off a shell in a single-wide space. He only manages a few bounces before the shell hits and kills him. Chuggaa then does shell trick perfectly, which Jon predicted immediately before.

*** Made even better by the fact that [[spoiler: NCS had a Lucky Lamp (an item that changes the star's location) for the entire game and never used it. Although he did win, so maybe that was the right choice.]]

** For the first part of the extras, they go through the lengthy instructions for ''Darts of Doom'', and then the minigame ends after one throw because Chugga [[{{Whammy}} hits the bullseye]]. Then Chugga picks the same minigame again by accident, though he admits that it lets them show more of it. And then Tim hits the bullseye. Jon never gets a throw.

** In Part 4 of Clockwork Castle, they crashed the game when they were about to play Sunday Drivers for the first time

* From ''VideoGame/MarioParty7'':

** Jon plays the AI in a 1-on-1 minigame during "Mii Fashion Plaza." The AI's ArtificialStupidity rivals that of Daisy and Wario from the ''Mario Party'' games, with it often just drifting to the side for no reason, moving as slow as possible, and always choosing the wrong pieces to match first. It ends up only scoring one point for the entire minigame.

** Tom Fawkes being the first person to go bankrupt, immediately handing the victory to [[spoiler: Tim. Although Tim would have won either way.]]

** In the Dunk Bros minigame, the guys talk about a failed recording where the score ended up 75-0. None of the guys managed to get a single basket, the AI just kept scoring three-pointers.

** On Jon's turn, the voice recognition in the "Speak Up" mode in ''Mario Party'' repeatedly fails to recognize the word... "Mario."

** During his solo board Chugga recalls a real-life failure: in elementary school two twins had a crush on them, one of them was heavier, and he said, "Oh, I get it, your mom fed you fatter so she could tell you apart!"

** For a second game in a row, Emile fails to win a single board.