Their run through Mario Party 9's Bob-Omb Factory. It's one thing for Holms to be repeatedly screwed over and get salty about it. It's another thing when the other players are able to guess how he'll be screwed over next, right down to individual die rolls.
As a bonus, the game then starts a round of "10 To Win" and hands him every single card. He doesn't accept the apology.
During the group's play-through of Mario Party 2's Space Land, Holms' gambit in a duel minigame late in the game against Steeler failed. Holms, who was having a rough game as it was, took himself out of the game by setting his controller to the Easy-level CPU. In the ensuing 3-vs-1 minigame, the Easy-level CPU Peach proceeded to take out Mr. Doom!
Similarly, after Holms ragequits after losing his coins to Steeler in their second Chilly Waters match, his uncontrolled character manages to get three times as many coins as Steeler in the next minigame.
On the Pirate Land board during LP Every Mario Party, Clel lands on Chance Time and the players state that everyone has a star except Clel. The outcome is Clel and Holms switching stars, causing Holms to run upstairs. Right after he leaves, everyone else realizes that it was Clel, not Holms, who bought a star earlier, and he just gave it to Holms. Cue a discussion over how he just ragequit over being given the lead.
Their second playthrough of Woody Woods lasts nine turns thanks to Mr. Doom getting the Wacky Watch, which when used automatically turns the game to five turns left.note They say eight in the video, but Mr. Doom used the watch on the fourth turn, making it nine.
In that same game Holms and Steeler duel each other for coins and end up playing Tick Tock Hop, where they have to jump over the minute hand as it and the hour hand rotate around the clock. They manage to last for seventy-two jumps before Steeler finally lost. If that doesn't sound impressive to you, the game lasted for roughly two and a half minutes.
Mr. Doom's computer crashed during recording of the Mystery Land playthrough. The funny part is that they didn't even notice for about a minute, so for a minute you're staring at the Blue Screen of Death while the game goes on in the background.
In the fourth season run of Mario's Rainbow Castle, Mr. Doom and Steeler are handed a lucky break in Handcar Havoc when their opponents fall off the track, so they decide to take the course more carefully. Until they reach a hill they don't have enough speed to pass, and end up going backward.