In Mario Party 2, medibot, who has no coins at the moment, lands on a Bowser space and gets "30 coins for Bowser." Since he has no coins, Bowser gives him some. medibot: Just as Planned!
And "I have gained an alliance with the Dark Lord Koopa."
Kung-Fu Jesus, who has been losing, lands on an item block and randomly gets a star.
pokecapn rolls two consecutive 10s in 2 to just barely snag the star.
pokecapn: Press your fuckin' luck! Let's GO!!
Pokecapn sweeping the bonus stars in Mario Party 2.
In Mario Party 3, Kaz makes Bowser cast his Reverse Curse on everybody. When Kung Fu Jesus's turn comes up, he goes and randomly discovers that he can just barely get a star. What makes it even more awesome is that the other three had been trying and failing the entire time.
medibot utterly cleans up in Tally Me Banana, complete with using Kaz and pokecapn as stepping stones — and immediately ending up at 11 stars and 111 coins as a result.
KFJ earning the most stars in Mario Party 7. This is never mentioned by the posse, and he doesn't actually win, but he gains six stars over the course of the game — more than even medibot, who collected five, including his bonus stars!
In fact, the gang's handicap system has made some of the games seem less interesting than if they had just kept everyone's star count at zero from the beginning of each game.
In Mario Party 3, if there were no handicaps, KFJ was in the lead for almost the entire game, and would have only lost to pokecapn by 14 coins if it weren't to Wario's two bonus stars.
Without handicaps in place, medibot would have won Mario Party 4 if he and pokecapn hadn't have tied for the Happening Star at the end.
This is averted with Mario Party 6, where the handicaps really do make the results seem more dramatic. Both KFJ and medibot started the game with eight stars while pokecapn began with zero. pokecapn would go on to collect eleven stars, tying with KFJ and medibot at the end, and winning the game thanks to getting two bonus stars (the other three players tied for the last bonus star). In the end, if Wario hadn't have gotten both the bonus stars he had, KFJ would have won with 12 Stars and 26 Coins, medibot would have gotten second place with 12 Stars and 24 Coins, and pokecapn would have gotten third place with 12 Stars and 23 Coins!
The reveal that Kaz was the minigame champion in Mario Party 8, breaking pokecapn's streak.
On his last turn in Mario Party 8, pokecapn considers that, while he is far behind in the game, he might be able to get a lucky bonus star if he lands on a red space instead of a blue space. So he does, losing three coins (six coins if you count what he passed up) in the process. He turns out to be absolutely correct, as one of the bonus stars awarded is for the most red spaces, and that final landing tied him for first, giving him a star. And then it turns out that he defeated medibot in the overall statistics between all eight games... by less than one star. That one red space won him the series. (That is, if the math turns out to be anything close to accurate.)
In Night Light Fright, the goal is to play "Chicken" with a chain chomp, shining a light on it to stun it closer than everyone else. KFJ stops his 5 yards away. Medibot and Kaz stop theirs 2 yards away each. pokecapn stops his 0.1 yards away.
In 9, during the Bob-Omb Factory Captain Event, Pokecapn, misunderstanding the rules, puts himself on the route with the least Mini-Stars. By a stroke of luck, he and Kung-Fu Jesus both happen to land on a ? Space, moving the conveyor belts so that he instead gets the maximum possible number of Mini-Stars.
In Sonic Unleashed, medibot listing the identities of every sun and moon medal in the game may be more funny than awesome, but true awesomeness can be attributed to WolfShirt, a viewer who submitted fanart of Sonic the Werehog carrying a Katamariesque ball of everything listed up to that point.
In order to properly LP this game, the Posse managed to put together this◊ insane hardware setup they call "the Gigaquad" consisting of four GameCubes with Game Boy Players to serve as Game Boy Advances, a Wii to run the main game on, and multiple computers to capture all five screens at once. Expensive probably doesn't begin to cover it.
pokecapn, realizing that he has a boomerang, grabs 1000 Force Gems a split second before Tingle takes them — with a resounding "FUCK YOU!" as the boomerang grabs his loot.
During the credits, the group objects to a shot of Death Mountain with Tingle surrounded by a massive quantity of Force Gems. As they point out, as much as they hoarded or stole the gems from each other, they stood by their principle of never allowing Tingle to get away with a single one.