Pokecapn/Awesome

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 gets all the bonus stars.
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: Well played.

The conclusion of this mini-game, wherein Kaz not only wins, but beats pokecapn's overall high score by thirty. pokecapn's reaction is priceless.
In Mario Party 5, medibot -- thanks to a golden mushroom -- makes it to the star space and its new location... twice in the same turn.
- Repeated in Mario Party 7 by Kung Fu Jesus. Twice.
Playing Fruit Talktail in Mario Party 6, Kaz defeats all three opponents with a single word. Bonus points for it being a Call Back to an earlier conversation.

medibot utterly cleans up in Tally Me Banana, complete with using Kaz and pokecapn as stepping stones.
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!
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 Sonic Generations, the battle with the Egg Dragoon, which the posse notes is perfectly matched to "Sonic Boom." The victory cutscene is even timed to the chorus.
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.