* From ''VideoGame/MarioParty1'':
** NCS profited a total of -4 coins from minigames in Luigi's Engine Room. That is to say, he lost more than he gained from them.
*** He does it ''again'' on Peach's Birthday Cake, profiting a total of -1 coins.
*** And '''AGAIN''' on Yoshi's Tropical Island, with -2 coins.
*** At the end of the Mini-Game stadium, both Jon and Chugga end with well over 100 coins (Chugga at nearly 200), and the AI had over eighty. Tim? ''2 coins.'' Since they started with 10, that means a total profit of -8!
** Jon completely fails to understand how to play Deep-Sea Divers in part 2 of Wario's Battle Canyon, dooming himself and Tim to leave empty-handed as Chugga and the AI clean up.
** Any time anyone steals only one coin from another player.
** Jon's HumiliationConga in the Yoshi's Tropical Island board. [[https://www.youtube.com/watch?v=RcGgA2OnsV0 You know the one.]]
--->'''Jon:''' "'''GAAAAAAAAAMMMMEE!'''"
** The only time they played Hot Rope Jump, they don't even make the first jump (Chugga landed on the fire rope). And the last time they played Running of the Bulb, all four of them get eaten and lose almost at the beginning.
** When they go back and do the Mini Game Island mode, Tim plays Bumper Balls as Wario, and loses immediately after losing track of his character.
** After talking up how he's going to redeem himself on "Knocka-Blocka-Towaah" after his failure in the main LP, Chugga does ''even worse''.

* From ''VideoGame/NewSuperMarioBrosWii'':
** NCS getting killed by [[spoiler:the first Goomba.]]
** Everyone except Josh getting killed by a Paratroopa in Part 2.
** The guys attempting to do a four-player ground pound ended with two of them going down a warp pipe by accident.
** After trying for a long period of time to get the third Star Coin in World 2-5 (and failing), LetsPlay/ProtonJon finally gets the coin... only to die two seconds later... while everyone else was in [[BottomlessPitRescueService recovery bubbles,]] forcing them out of the level without saving their Star Coins.
** At the end of episode 6, the death chart shows that NCS has ''79 deaths''.
*** At the end of the same episode, LetsPlay/JoshJepson has a total of ''77 deaths''. Only 2 deaths behind NCS.
** In the first fortress in World 5, they spend 5 minutes trying to get up one section, and there are a lot of deaths throughout the level.
** Episode 14. Levels 7-4 and 7-6. And the death count at the end: Jon 19, Josh 29, Chugga 43 and NCS 47. Granted, it was a long episode, but still.
--->'''Jon:''' "I think we just pulled a LetsPlay/FreelanceAstronauts."
** World [[spoiler:9-3, second Star Coin]]. Half the time they ''get'' it, but collectively die trying to make it to the end of the stage.
** A subversion happened in episode 15 at the second try of level 8-2, when NCS ended up getting on the very top... only to bubble at literally the '''exact point''' of the very top of the pole. Instead of not getting anything at all, he ended up getting a 1-Up and some fireworks, yet he never appeared on the ground at the end... ''[[https://www.youtube.com/watch?feature=player_detailpage&v=d5heDCBsKPU#t=865 at all]]''.

* From ''VideoGame/SuperSmashBrosBrawl'':
** 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.'' And they don't realize it's crashed for nearly 30 seconds, talking over the system buzzing in the background.
** Then, when they reboot the system, they forget to enter Tim ''again''.
** Episode 8 goes by quite swimmingly until The Wilds 2, where Chugga and Tim keep meeting their demise at the hands of... [[https://www.youtube.com/watch?feature=player_detailpage&v=xRFw-vjDeo8#t=1155s simple lifts]].
--->'''Video Description:''' Elevators: Apparently something only Canadians understand.
** Duon vs. Jon and Tim. It does not go well.
** Tim keeps going the wrong way in the maze, making Jon and Chugga yell at him a lot.
** [[https://www.youtube.com/watch?v=IKZ0bYO3NNo The Bonus Episode]]. Tim's quest to fight and unlock Jigglypuff. It has to be seen to be believed.
*** How bad does it get? [[spoiler:After overshooting the door and having to swim back through a maze of Jyks and barrel cannons, Tim fires himself off the stage and loses to Jigglypuff within seconds, causing them to have to start over. Jon (who's playing shotgun) actually puts down his controller and walks away in frustration.]] Tim doesn't hate him for it, saying in a later video he knew he was sucking and deserved that response.
** During the fight between Chugga and Josh, Chugga uses a PK Starstorm and completely misses Josh, even though the attack basically covers the entire screen.
** In an earlier match, Chugga is killed by a rolling crate spawning and smashing into him, costing him the match.
** In the tournament fight between Lucahjin and [[LetsPlay/SKArmedageddon SyKhotic]], Lucah manages to leap off the edge of the stage and commit suicide in roughly the first ten seconds of play. And then proceeds to be thoroughly destroyed by both [=SyKhotic=] and the rising acid below them.
** A meta-example: The three were playing this game at E3 and it took them a ''half-hour'' to realize that they weren't recording.
*** In [[https://www.youtube.com/watch?v=TXwbGmk-6oU this live stream]], Chugga explains the entire story. All of the Guys forgot to bring the game, so Chugga went to a Best Buy and ended up spending $131 in total for it and the cab fare. They did not have enough controllers, so Jon went to buy them from a Game Stop. After an hour, Jon texted Chugga that it would take two more hours for another cab to arrive. Chugga tried to go pick him up only for his own cab driver to get lost (and refusing to take off fare). As soon as he arrived, Jon got a phone call saying that his cab was coming early, so Chugga went all that way for nothing. When they returned to the hotel and tried to pay the driver, the taxi's debit card reader turned out to be broken. Chugga went inside to withdraw money from the ATM, which was also broken. He went to the front desk and asked for cash back, and they said they couldn't do that. Chugga and Jon had to go back in the cab and ask the taxi driver to go to a bank so they could withdraw cash, driving up the fare to $60. When they went back to the room and were about to start recording, they found that they forgot to pack a cord that was necessary for the capturing to work. Jon and Chugga walked to a Radio Shack a whole 2 1/2 miles away to buy this cord for $38. It took them an entire SEVEN hours to get everything set up for recording and start playing the game, [[EpicFail only to find out that they actually weren't recording anything after 30 minutes.]] According to Jon, it was the first time he had ever seen [[ThePollyanna Chugga]] get legitimately angry, and Chugga was so depressed he didn't want to record anymore.
* From ''VideoGame/MarioParty2'':
** In Space Land, Jon lands on the happening space ''six times''. For people unfamiliar with Space Land, the Happening Space causes the player who lands on it and anyone else on the same stretch of land to move back to a certain space.
*** This really burns Emile in his LP with LetsPlay/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.]]
--->'''Emile:''' "'''OH MY BARK!'''"
** Horror Land's first minigame, Hexagon Heat, [[http://youtu.be/67pNhxEQ5xA?t=2m15s lasts six seconds]] due to everyone but Chugga having an EpicFail moment.
--->'''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's case was actually justified; his controller was glitching and forcing Yoshi to move upward when he was supposed to go down. This actually happens again later during a game of Face Lift, as you can see his hand moving upward automatically and giving him extra trouble.
*** The thing is though that Tim NEVER seemed to realize his controller was glitching.
** On Mini Game Coaster, Chugga is about to win, but then asks why he's losing, and instantly lost. The kicker is that [[spoiler:he was looking at the wrong character for the whole game, and would have won without noticing if he hadn't stopped]].
** Later still, [[spoiler:Jon's long win streak finally ends]] because he lost Quick Sand Cache by ''one coin''.
** In Episode 3 of Western Land, the guys play the battle minigame "Raken' 'Em In". Close to the very end of the minigame, Chugga is in second place with the AI (Wario) with 5 points. [[spoiler:Then he attempts to grab the hard-to-get Golden Mushroom for three extra points as the counter reaches 0, and ends up getting a Poison Mushroom instead and loses 3 points, knocking him down to 3rd place with NCS with 2 points. If he haven't have done that, he would have gotten 2nd place and get a small profit.]]
** Horror Land: Chugga is close to the Mega Boo of the board, and needs to get anything but a 1 to get to him. [[spoiler:He gets a 1, much to his displeasure.]]
** At end of Episode 1 of Western Land, the guys play the 2 vs. 2 minigame "Torpedo Targets", with Chugga & NCS vs. Jon and the AI (Wario). Jon must steer the torpedo, much to his dismay. [[spoiler:Made even worse when Wario keeps missing the target. Completely.]]

* From ''VideoGame/KirbysReturnToDreamLand'':
** Episode 11 had Chugga, after getting the key, try to throw it because he thinks he might not make the jump. [[spoiler:He accidentally throws the key down the pit.]]
** Episode 8 had a grand total of 11 deaths because of their inability to stop falling into pits while operating the shoe vehicle.
** Episode 9 is basically the trainwreck episode for this series. Tim ends up with two [[TotalPartyKill Total Party Kills]] from firing off cannons in 6-1 and they spend 12 minutes (after editing, mind you) trying to get the first gear in 6-2 due to Chugga constantly either dying or losing the water power required to break the fire blocks surrounding it.
*** A shining example of their failure with items is [[https://www.youtube.com/watch?v=ZfXZ7KYeH6w#t=19m3s here]], where Jon runs offscreen and teleports to Emile's place while Tim goes into the door right before they get the gear.
** Emile accidentally causes Jon to lose a potential perfect rating on the [[BrutalBonusLevel item challenge room]] at the last second.
** Tim's Hi-Jump run starts out with him slowly flying instead of jumping and getting a -100 score for running into an enemy. He hits a switch that closes off a +1000 gold coin and jumps around two more gold coins under a ledge, then proceeds to move away from the secret room ''he was right in front of'' and go into the next area. After that he keeps jumping up when he wants to go down, smacks into a Gordo, and then ignores the other secret door above the goal. His score was 2000 points lower than his previous, and the worst part is that ''he just practiced this right before the recording''.

* From ''VideoGame/WiiParty'':
** On ''Board Game Island'', Tim does pretty well for the first part, winning a fair amount of the minigames. However, near the end, his luck fails him and his die rolls send him first backwards across about a quarter of the board, then into hell (what Jon calls the volcano), resulting in him being ''46'' spaces away from the end when it finishes.
** A [[https://www.youtube.com/watch?v=3NH5T01ruQc#t=2m15s real life example]] talked about in Globe Trot. To cross the middle of a road in Canada, there are buttons for alerting cars to stop and let people pass. Emile and Tim pushed said button for the first time and caused an accident by making a guy rear-end his car. Nobody was hurt, though.
** In ''Swap Meet'', not only does Tim [[CurbStompBattle Curb Stomp]] the others by finishing with twice as many points as everyone else combined, Chugga doesn't even manage to score a ''single'' point.

* From ''VideoGame/LittleBigPlanet'':
** In episode 5, they try and fail for several minutes to bring a few bombs through some dropping stalactites, and end up using ''three gates' worth'' of lives to finally successfully make it through. To add insult to injury, Tim had made it through with the last bomb fairly early on, but then ''missed the bombable floor'' when he dropped it, prompting:
--->'''Tim:''' "''D'oh, I missed!''"
** Episode 6, Roller Run - Hard: Close to the beginning, they find a gate, and Jon asks, "How did we get another gate that fast?" 15 seconds later, they've used all their lives and fail out of the level.
** In episode 11, they get a minigame where they all die instantly, then try again and the three usual Guys all die instantly and Lucah wins 57-0-0-0 by surviving a few seconds longer.
** [[ThatOneLevel The Bunker]]. In this episode alone, they have 255 deaths combined. 201 of those deaths were from electricity.

* From the ''[[VideoGame/SuperSmashBros Smash 64]]'' tournament:
** LetsPlay/JoshJepson's fight with Creator/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]].

* From ''VideoGame/FortuneStreet'':
** Not only has Chugga ended in last place in the first two boards played, but he was been very far behind both times. Sadly (and hilariously), he likes to talk about how well he does when he plays by himself. [[spoiler:Which he finally gets to show in Mario Stadium.]]
** Tim in Delfino Plaza, squandering a near-sure win by turning down a property in Jon's district that would have kept Jon from total domination, then paying more than 1000G for one of Chugga's auctioned shops worth a fraction of that, that he didn't even want or need. The other players started joking that he threw the game, and one of Tim's vlogs at the time mentions how he epicly fucked up a Fortune Street board.
*** Buying the shop at auction wouldn't have mattered; Jon got back to the bank first anyways.
** Their guest player accidentally buying out a shop they didn't need. ''Three times''.
*** What takes the cake is that it wasn't even the same player any of the three times: The first time it was Josh, the second time it was Jake, and the third time it was Masae.
*** Masae also failed to buy a shop during the Castle Trodain match. Jon [[spoiler:bugs her out for it by repeatedly creepily telling her she should've bought the shop in question.]]
*** A third shop-based blunder from Masae, this time at Alefgard. She has a monopoly, but hasn't bothered upgrading the smallest shop. [[spoiler:Jon snipes it, then goes on to deny her the first guest win when another Jon shop bankrupts Emile. And then the game itself rubs salt on the wound by advising exactly what she ''didn't'' do leading to her loss. And then Tom succeeds at winning a board.]]
** Tom Fawkes being the first person to go bankrupt via a $4000+ space, immediately handing the victory to [[spoiler: Tim. Although Tim would have won either way.]]
** 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: be short by a whopping 1G on a debt, auction off his shops, one by one, including TWO monopolies, and nearly go bankrupt.]]
** In Bowser's Castle, after Jon jokes that Tim should choose the small block in Memory Block, with a guaranteed Bowser card, he actually chooses it. He was very much in last place at the time, too.

* From ''VideoGame/NewSuperMarioBrosU'':
** It takes three attempts to get all of the star coins on the ''second level''.
** Josh dies 15 times in Episode 6, after several episodes of not dying at all. And unlike Tim, he doesn't have the excuse of the others being jerks.
** Everyone dying, as in ''kicked out of the level'' dying, in a stage where the majority of the threats are limited to the bottom half of the screen -- ''after using a [[GameBreaker P-Acorn]].'' It's an achievement in and of itself!

* From ''VideoGame/BurnoutRevenge'':
** Lucahjin manages to [[spoiler:miss all the passing cars and go straight past without hitting anything]].

* From ''VideoGame/MarioParty3'':
** NCS uses his Lucky Charm on Chugga to force him into a Game Guy game with 153 coins. Chugga won it, doubling his coin count to 306 and effectively winning the Coin Star.
** The first minigame, Ice Rink Risk, has the Guys consecutively dying ''less than a second'' after each other.
** Wario's AI on the first board reaches heights of ArtificialStupidity that have to be seen to be believed, especially when he spent 10 coins on a Dueling Glove so he could duel Jon for ''one'' coin.
** The first Star in Deep Bloober Sea is placed behind a locked door, requiring either a Skeleton Key or Reverse Mushroom, and a victory in a luck-based event, to reach it. [[spoiler:No one ever gets it. The final tally consists solely of a Star from a hidden block and the Bonus Stars]].
*** 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. The hidden block with a Star in it was also Tim's, his third such hidden block of the game after getting two Skeleton Keys from the first two.]]
** Jon's chain of item game failures. Most egregious is when he plays a game where ''he could easily walk and pick the item'', only to accidentally pick an item he didn't want.
** In Part 3 of Spiny Desert, Chugga buys a Mushroom and finds himself 15 spaces away from the star, so he has a decent chance of reaching it. He rolls a 2 and a 1, which he describes as the worst possible roll, as you at least get a coin bonus for rolling two 1's due to rolling doubles.
** In Part 4 of Spiny Desert, Tim lands on a Chance Time space. He tries to [[spoiler:steal Jon's Stars, as Jon was in the lead at that point, but it backfired when he accidentally gave Jon's Stars to Peach instead. Jon lost his lead, and Peach rocketed to first place]].
** In Creepy Cavern, Jon gets the rare Koopa Kard, which allows one to receive all the money in the bank, as if they had landed on it, by just passing it. Chugga schemes to steal it with a Plunder Chest, and succeeds...only to accidentally use up the Koopa Kard when he landed on the bank anyway, rendering the item completely pointless.
** Also in Creepy Cavern, the AI builds up a massive coin lead of ''596'' via Game Guy, so Chugga tries to steal the AI's coins via Chance Time. He successfully manages to land the Chance Time slots on "all coins" and "DK receives," but messes up by making Tim the giver rather than the AI, so he just gets Tim's 13 coins.
** In Waluigi's Island, Chugga passes the item store and ends up 2 spaces behind Wario, who has a lot of coins, so he buys a Bowser Suit. All he has to do on the next turn to steal coins from Wario is roll anything higher than a 1. Guess what happens.
** Jon and Chugga race for a Star. They are both 10 spaces away from it, the maximum possible roll. Jon rolls an 8, lands on Bowser and loses three-quarters of his coins. Then Chugga rolls a 10 and gets the Star.
*** [[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 pay him back for the stolen Koopa Kard.]]
--->'''Emile:''' "'''OH FRICK!!'''"

* From ''VideoGame/DokaponKingdom'':
** On the last turn of their test game, Chugga pays Mitch Digger 5440G to build hot springs, with a 4 in 7 chance of success. Rather predictably, it fails, though this isn't the best part. The final results show that Jon beat Chugga by 4837G. In other words, that single failure ''cost Chugga the game''.
** In Part 31, Chugga is revived after being killed by the Darkling. His first act is to fight a random monster... and ''immediately'' get killed ''again''.
** Out-of-universe example: Between episodes 53 and 54, Chugga somehow lost the commentary audio for an entire 2-hour session before he started editing, despite several backups. This delayed episode 54 by ''seven months'' until the Guys could get back together and record some post commentary.
** Episode 56: Jon fights The Big Boss monster on Granada, whittling it down to 38 HP. It then proceeds to kill ''all three'' of the Guys (killing Tim ''twice'') and then healing itself, before Chugga finally takes it down with a Counter, for which the king gives his bonus payment to Tim and Jon instead.
** Also from Episode 56: Jon tries to show off the Alchemy power (which gives you money based on damage done during a fight), only to have the enemy Give Up, netting him no gold. This happens ''twice'' in a row.
** Episode 102: Jon, having chosen Robo Knight and explicitly mentioning being able to use the class skill against the Darkling, picks a fight with said Darkling who had been weakened by a prolonged fight and a plague, and promptly forgets to use the skill when the time comes. The Darkling survives by the skin of his teeth.

* From ''VideoGame/NewSuperLuigiU'':
** Episode 8 is a gong show in and of itself, when they die several times trying to beat Wendy's Thwomp Castle, but the kicker is when, at the start of one attempt, everyone ''immediately bubbles'', kicking them out of the stage.
** In episode 23, for once Jon has the most deaths of anyone (13), largely down to [[BerserkButton Slippery Shoes]].
** After going the entire game without using a continue, [[spoiler:Tim loses all his lives on the very last level and has to use one]].

* From ''Series/WheelOfFortune'':
** What does Chugga guess for the third minigame? C[[spoiler:A]]L[[spoiler:I]]BR[[spoiler:AR]]Y C[[spoiler:UF]]F PAUL[[spoiler:A]] D[[spoiler:E]]E[[spoiler:N]].
*** That actually describes how he does in ''Wheel of Fortune'' overall. Down to the point he was off by [[spoiler:one letter]] at least once.
** Chugga and Tim both buzzing in too early on the same word, giving Jon the win.
--->"''I'm just gonna sit here and wait for the word to fill itself out.''"
** An uncharacteristic goof by Tim: Chugga tries to solve [[spoiler: Faneuil Hall]]. He fails. Tim tries to solve it, using the exact same incorrect guess as Chugga. Keep in mind only vowels were remaining, so there were only four possible configurations.
** In Hawaii, Chugga has a hilarious failure when he gets stumped on a puzzle that clearly reads "The Metropolitan Museum of Art", somehow filling in [[spoiler:T]]HE ME[[spoiler:TR]]OPO[[spoiler:LI]]TAN MU[[spoiler:TANT]] O[[spoiler:F]] AR[[spoiler:K]] instead and almost giving Jon an aneurysm.
*** That round ended up being an epic fail for all three of the Guys: Immediately after Chugga's blunder, Tim gets a chance to solve the puzzle, and [[spoiler:almost gets it right, but accidentally hits "enter" without typing in the final letter, giving the turn to Jon.]] And finally, despite the aforementioned failures from both of his opponents, [[spoiler:Jon ends up in last place on that round due to bad luck with spinning. Yes, he ended up scoring lower than CHUGGA!]]

* From ''VideoGame/MarioParty4'':
** Playing the "Hide and Go BOOM!" minigame, NCS fails to press a button to hide in one of the cannons, and ''automatically loses by default''. [[spoiler: His team still won though, so Yoshi won by doing absolutely nothing!]]
** At the end of Episode 1 of Shy Guy's Jungle Jam, Chugga uses a Mega Mushroom, and since everyone's close by this means he can steal from all three of them. [[spoiler: He winds up only rolling two ones. This is subverted however, since rolling doubles still winds up netting him money!]]
** Part 5 of ''Goomba's Greedy Gala'' has Daisy's A.I. rival Wario's ArtificialStupidity:
*** First, Daisy and Tim are both merely 5 spaces away from a Star that has just appeared and Daisy's turn has come first. She chooses to waste a mini-mushroom on herself ''for no reason'', making her roll too low and giving the star to Tim!
*** Immediately after this comes [[http://youtu.be/ze5cz3-QCrk?t=5m47s Tree Stomp]]. All three players chasing Jon corner him -- then manage to get themselves stuck for the ''entire round'' due to Daisy refusing to budge, giving Jon an easy win by doing absolutely nothing.
*** Now animated as, fittingly, [[https://www.youtube.com/watch?v=09nV_q4QS6E Between A Rock and a Hard Place]].
** 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. Neither does the AI.
** At the end of the second extras video, Chugga and Jon play Panels of Doom, a game in which two players roll dice while standing on numbered panels, and the first one to have their number rolled loses. Chugga chooses panel 7 and Jon chooses panel 8; Chugga gets the first roll. [[spoiler: Chugga rolls a 7, killing himself instantly.]]
** At the beginning of the second extras video, in ''The Final Battle!'' Tim is controlling DK in a platforming segment where he has to get through a bunch of fiery platforms while avoiding falling into the lava. Almost immediately after making his first jump he ground pounds straight into the lava, losing instantly.
** After four Mario Parties, the Guys finally fail to [[spoiler:stop the AI winning a board, albeit a bonus one rather than a main game one]].

* From ''VideoGame/SuperMario3DWorld'':
** Episode 3 starts out with the reveal that [[spoiler:nearly everything's completed in the game and they had to redo this part because of a technical problem that didn't have the sound coming out there at all! Thankfully that's the only episode where that problem occurred (at least so far), but the point still stands there.]]
** Jon and Masae manage to kill themselves by playing GrenadeHotPotato with a Bob-omb on some breakable blocks over a pit.
** 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. Chugga then does the shell trick perfectly, which Jon predicted immediately before.

* From ''VideoGame/SonicAdventure'':
** Episode 1 has Chugga die to the first boss. In less than 10 seconds.
*** And he would've died even ''sooner'' had Sonic not picked up a ring in the cutscene, which actually makes this an even bigger fail, having a safety net before the boss battle even began.
** In Episode 33, Emile accidentally drives off the track in the very linear and hard-to-screw-up racing minigame.
** In Episode 34, Tim manages to die as Big the Cat ''twice'' in the Emerald Coast stage. The first time is understandable: he breaks his line trying to reel in a Hammerhead Shark. The second... isn't. Tim gets too sidetracked and manages to drown ''as Big the Cat'' trying to enter the secret cavern.
*** The very fact that it took Tim at least seven minutes to beat the stage.
*** The very fact that all three of the Guys end up losing at least one life ''as Big the Cat''.
** Jon getting a Game Over in Episode 41, not by dying to a boss or some hazard in a stage, but by falling through a tiny little crack in a raft in an ''adventure field''.

* From ''VideoGame/SuperMarioBros3'':
** Chugga dying twice on [[spoiler: World 1-1.]]
** Chugga losing a whopping [[spoiler: 12 lives]] in the invincibility star run stage.
** Chugga dying to [[spoiler: Boom Boom]] in the boat stage in world 8. This makes Chugga the first to die to them.

* From ''VideoGame/MarioParty5'':
** When Jon practiced the game before recording, he played with three AIs. The final score was: 7 stars and 11 coins, 7 stars and 0 coins, 3 stars and 56 coins, and 0 stars and 28 coins. Guess which one was Jon?
** Toy Dream Part 5 has [[spoiler: the AI finally winning a board, but that is not the worst of it. Chugga lost the board by one coin in what seems to be karma finally paying him back for his "Suck it Slim" comment from Mario Party 1.]]
*** Even worse for Emile, [[spoiler:it was the same AI who got Slim in his playthrough for the same Bonus Star.]]
** In mini-game ''Squared Away'' during Rainbow Dream Part 3, Jon gets crushed by Luigi in just two seconds all because he accidentally pressed up.
** Rainbow Dream Part 4 has Jon getting a Thwomp in ''Vicious Vending'' while everyone else got coins, continuing his unfortunate losing streak with this mini-game. What makes it more bad luck for Jon is that this is the [[HopeSpot first time only one Thwomp appears instead of two]] and he still ends up on the short end of the stick.
** Chugga loses ''Heat Stroke'' in Pirate Dream Part 1 by jumping off the map, thinking there'd be an invisible wall.
** Chugga, of ''[[BornLucky all people]]'', ends the main game without a single board win.
** During ''Super Duel Mode'' part 1, Jon builds a car with great firepower and intimidation -- but almost zero speed. He loses in seconds.
*** Then there's his famous first attempt at Yoshi in the Hard Tournament.

* From ''Kirby's Dream Course'':
** Hole 6 of the Whispy Woods course: Jon suggests that Tim slam into Chugga to knock him off the course and miss a turn. The terrain, the amount of power in Tim's shot, and Tim aiming just off to the side of Chugga cause him to ''bounce over'' Chugga ''and'' Whispy[[labelnote:*]]who would have bounced Tim back towards Chugga[[/labelnote]], and fall off the course instead.
** Hole 1 of Mr. Shine & Mr. Bright has Tim just ''barely'' short of the hole... but close enough so that when Jon shoots for the hole, he hits Tim, causing Tim to get the stars for the hole ''even though Jon went in''.
** The same happens with Chugga and Jon in hole 2 of the Kracko course as Chugga aims to hit Jon and triggers Tornado, only to hit a vent, go flying above Jon, but have enough momentum to bounce back and enter the hole. However, his hitting Jon causes Jon to get the stars over the hole back!

* From ''Four Swords Adventures''
** Taking nearly ''five'' minutes to figure out how to get past the second screen in Episode 5. Most of it is simply trying to stand on the same spot and hoping something different happens.
** The entirety of the Village of the Blue Maiden. None of them ever seem to figure out the puzzles except through trial and error and are frequently screwed over by poor communication. Their difficulty reading the Gameboy screens due to their setup can be partially blamed. It's so bad that upon completing it, they proceed to swear a vendetta against "town levels" and get preemptively worried and angry when they show up in the future.
** Doubles as a SugarWiki/{{Funny Moment|s}}, but Episode 15 amounts to over twenty minutes of them failling to infiltrate Hyrule Castle and getting thrown in jail. ''Sixteen times.''

* From ''VideoGame/MarioParty6'':
** In Faire Square, Jon rolls ''5'' consecutive 1s. One of them involved rolling triple 1s on a Super 'Shroom Orb, [[BornUnlucky much to his dismay]].
** In Part 4 of Clockwork Castle, they crashed the game when they were about to play Sunday Drivers for the first time. [[spoiler:Tim loses a Star he got through Chance Time from Emile because it was that same turn he got it.]]
** The AI wins Freeze Frame in part 6 of Clockwork Castle because no one else scored a single point.
** For a second game in a row, Emile fails to win a single board.
** 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!"
** On Jon's turn, the voice recognition in the "Speak Up" mode in ''Mario Party'' repeatedly fails to recognize the word... "Mario."
** 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.

* From ''VideoGame/WiiPartyU'':
** 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 mini game.

* From ''VideoGame/MarioParty7'':
** During a game of Tile and Error on Grand Canal, Mario punches Jon, his ''own teammate'', off the board.
** 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.

* From ''VideoGame/SanrioWorldSmashball'':
** 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/MarioPartyDS'':
** 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.
** Jon attempts to use the roulette wheel in Bowser's Pinball Machine... without any coins.
-->'''Jon:''' Oh. I didn't think that through.
** Thanks to the game's unending cruelty towards him, Jon -- for the first time ever -- goes a ''Mario Party'' without winning a single board, meaning all three guys have gone at least one ''Mario Party'' without winning a single board.