* EarWorm: Turn the music on. [[SchmuckBait Go ahead]].
* GoddamnBats: ''Teeth''.
** Also Walkers.
** Also Blobs.
* FauxSymbolism: Levels 54 (''Grail'') and 142 (''Pentagram'').
* IAmNotShazam: While ''Chip's Challenge'' does star Chip, ''Chuck's Challenge'' doesn't star Chuck; you play as Woop, playing through puzzles ''created by'' Chuck.
* MostAnnoyingSound: ''Bummer!''.
** If you're in a level where an enemy is controlling the buttons, expect the constant BOP-BOP-BOP to drive you mad until you turn the sound off.
* NightmareFuel: Teeth are damn creepy when you're playing this as a kid. It doesn't help that they're the only enemy that actively pursues you.
* PortingDisaster: The Windows version introduced several glitches, most notably certain buttons not working consistently.
* ThatOneLevel:
** Level 33, ''On The Rocks''. It's your first real MarathonLevel, having you use a block generator to build bridges to get to tiny islands with the chips on them. It's exceedingly time-consuming because there's only a handful of generators throughout the level, and if you make ''one'' slip, you'll have to restart the level.
** Level 73, ''Morton''. You're '''not''' going to beat it if you can't trap the teeth within a spot from which it can't bother you anymore.
** Level 89, ''Block Buster''. The speed of the blocks that are replicated by the clone buttons makes them ''very'' difficult to dodge. And since Chip is a OneHitPointWonder, he must ''never'' fail at dodging any of them.
** Level 105, ''Short Circuit''. A nasty maze of chip sockets and recessed walls, which forces you to memorize the layout of the maze.
** Level 131, ''Totally Unfair'', which requires you to memorize the layout of a previous level, titled ''Totally Fair''.
** Level 136, ''Doublemaze''. It's [[ExactlyWhatItSaysOnTheTin two mazes]] shuffled together. There's a huge amount of chips to collect, you need every single one of them, and thanks to the level design (ice and thin walls) it's hard to tell which maze a given chip is in.
** Level 147, ''Force Field''. Pretty much any level that takes longer than 5 minutes, for that matter. Sometimes a level with a time limit of under a minute is even worse.
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