* MagnificentBastard: Mr. Glitch once goaded Mathman into a long rant, getting him to ignore the time limit.
* MemeticMutation - One One Two Three
** Five Eureka!
* MomentOfAwesome - Any time Mathman won a free game would be enough to qualify, but the segment where he successfully argued against Mr. Glitch's claim that arithmetic and mathematics were the same thing deserves special mention.
** Glitch got Mathman back in a later episode, where he successfully provoked Mathman into going into a rant about how every occupation uses math in some capacity... before revealing that he agreed with Mathman all along, but just wanted to distract him from the time limit clock that just expired. Game Over.
* NightmareFuel - Mr. Glitch was an anthropomorphic tornado who would eat Mathman if he got a question wrong [[spoiler:and even once, when Mathman got it right]].
** And once for absolutely no reason at all. That time, [[NightmareFuel he filled the whole damn screen]].
** There was also one time when the roles were reversed and ''Mr. Glitch'' got to run the maze. In the end, after his (inevitable) failure, Mathman ate him [[LaserGuidedKarma ''one bite at a time.'']]
*** That happened more than once, and in some cases, Mr. Glitch [[AssholeVictim got eaten]] by [[HumiliationConga Mathdog]].
** And let's not forget the immense creepiness of the battles between the pluses and minuses... A [[http://www.youtube.com/watch?v=53dSP5IM5CY visceral testament]] to the simplicity of arithmetic and the futility and horrors of war.
** The "Ghost of a Chance" video. The whole concept of a pizza delivery boy getting trapped in a haunted house forever, unless he gets very lucky making a series of random guesses (to teach probability), is nightmarish enough, but then you have real footage of thousands of worms crawling over each other and an endless hallway with "EXIT?" signs over an endless number of doors. He picks the wrong one.
** Two words. ANGLE. DANCE.
* WhatDoYouMeanItsForKids - Some of the ''Mathnet'' segments were particularly dark at times, particularly "The View from the Rear Terrace", which has Kate Monday bound and gagged in her apartment with her neighbor's homemade bomb, and "The Case of the Masked Avenger", which has the mob blackmailing a wrestler over an opponent's death 20 years ago.