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1* ComeForTheGameStayForTheMods: ''Chip's Challenge'' has enjoyed a very robust modding community, with fans working upon the game's engine to design their own sets of levels and showcase a widespread array of difficulty and creativity. The most popular levels were voted and assembled into Level Packs. The original game alone amassed four such packs.
2* ComplacentGamingSyndrome: The vast majority of players tend to play the MS version over the Lynx version, mainly because its various glitches and design flaws make it the better version to SpeedRun.
3* DisappointingLastLevel: The original game has the 149th, final level (called ''Special''). The previous levels that are part of the final lineup of challenges are great (''Cake Walk'' is a deliberately-misnamed difficult level that requires careful use of blocks and the items present; ''Force Field'' is a gigantic labyrinth made of conveyor belts; ''Mind Block'' is a compact, yet tricky chamber filled with {{Cartoon Bomb}}s), but ''Special'' is anything but. The only two things you have to do to complete it (and the game) are: open the four colored doors with the corresponding keys (which is too easy), then find the exit in a hide-and-seek game involving blocks necessary to cross the water moats, but some of which are booby-trapped with fire that kills Chip instantly (which is too hard). And as with many other levels in the game, here you can see the worst side of the gameplay differences between the Microsoft and Atari Lynx versions: In the latter, you can slap the blocks to move them without touching the fire; but in the former you can't and thus you have to rely on trial and error. Have you just got burnt with ''one'' fire tile? Time to restart and open those doors yet again. Fortunately, the Level Pack {{Fan Sequel}}s as well as the official sequel (''Chip's Challenge 2'') all end with a ''much'' better final level each.
4* EvenBetterSequel: ''Chip's Challenge 2'', which basically takes the first game and adds Melinda as a playable character with her own set of rules and a metric ton of new puzzle elements.
5* FauxSymbolism: Levels 54 (''Grail'') and 142 (''Pentagram''). They're shaped after a cross and a pentagram, respectively, but they're otherwise normal levels.
6* FirstInstallmentWins: Between ''Chip's Challenge'' and ''Chuck's Challenge''. Knowledge of ''Chip's Challenge'' and its mechanics (both in the original Lynx version and the MS port) has risen dramatically over the years, and fans are still creating custom level packs to this day, most of which tend to be very well-designed. In contrast, ''Chuck's Challenge'' is mostly unknown, suffers from sketchy controls (at least in the iOS version), the built-in levels are fewer in number and are generally of lower quality than the ones in ''Chip's'', and the user-generated levels are mostly terrible.
7* GeniusBonus:
8** The "[=eProm=]", at first glance, sounds like a typical attempt to make something sound digital by adding the letter "e" to the front. However, it gains a new level of hilarity once you know that there's a certain type of memory chip called "[[https://en.wikipedia.org/wiki/Eprom EPROM]]".
9** The message for completing Level 144 in the Steam version of [=CC1=] is "That was totally gross, Chip! Now, just five more!" This may sound like an emulation of the TotallyRadical slang in the original decade messages, but it also references the ''noun'' "gross", meaning twelve dozen (or 144).
10* GoddamnBats:
11** Teeth monsters, due to their habit of permanently going after Chip.
12** Walkers and Blobs, due to their erratic movements which makes them unpredictable.
13* 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.
14* 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.
15* NintendoHard: The game is not easy in any way, first due to the many enemies that can easily kill Chip, and second because there are several puzzles that take a long time to solve. And the game is still easier than the {{Fan Sequel}}s.
16* PortingDisaster: The original Windows version lacks the smooth, fluid movement and animation of the original game and its numerous other ports; most noticeably, Chip and monsters "jump" from tile to tile instead of moving between them. In addition, it has several bugs that totally [[GameplayDerailment break the way that some levels were intended to be played]] (in some cases [[GoodBadBug for the better]], in other cases [[FakeDifficulty not so much]]). Yet, in an interesting case of Administrivia/TropesAreNotBad, this version is by far the most well-known due to its wide distribution and has still long been adored by thousands of players; in fact, most people introduced to the game on Windows didn't even know about the original game's mechanics until they were resurrected in ''[[GameMod Tile World]]'' and later the [[VideoGameRemake remake]]/sequel. The latter even has an option that [[AscendedGlitch emulates]] the "tile jumping" for those who are more comfortable with it. It's also the version of choice for speedrunners, since several glitches allow levels to be completed much more quickly than normal.
17* SequelDifficultySpike: Whereas the first game was nice enough to start you off with some simple levels in order to ease you into the [[NintendoHard intense difficulty]] that later levels would offer, ''Chip's Challenge 2'' starts throwing nasty tricks at you before the level count even reaches double digits, and it's only uphill from there thanks to all the new puzzle elements to contend with.
18* ThatOneLevel: For most players, any level that takes longer than 5 minutes. For others, a level with a time limit of under a minute is even worse. Notable examples include:
19** Level 23, ''Blobnet''. For the first appearance of blobs in the entire game, having to deal with '''80''' of them while trying to collect 88 chips, where ''any misstep means you have to start from the beginning'', makes this a huge DifficultySpike, and the most difficult level in the first half of the game.
20** 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.
21** Level 61, ''Rink''. Did you want a SlippySlideyIceWorld where you can't tell whether a direction is open or will bounce you back until after you've slid? No? Too bad, because this level is exactly that for the entire map. "Thrash-a-thon", indeed. This one is particularly bad because there's no way to die on it, meaning you can't just kill yourself until you're prompted to skip it.
22** Level 73, ''Morton''. At first, it looks like you're getting a nice simple maze level. As you move around, you quickly discover it is full of hidden walls blocking what appear to be open routes, making it a rather ''less simple'' maze level. You then discover that the centre of the maze contains a Teeth (often known in the fandom as Morton) who will chase you through the narrow corridors and can easily trap you if you can’t find a way to trap it first, making the maze the least of your problems.
23** Level 87, ''Cityblock''. You thought you hated block puzzles before? Get ready to despise them as you have to contend with ''four'' of them in one level (one of which doubles as a KaizoTrap, since it's located after the chip socket and can block you from reaching the exit if you do it wrong). With a long completion time, even for a perfect run, and the game's trademark airtight window for error when it comes to block puzzles, you'll likely have had more than your fill of block puzzles by the time you finally finish this beast.
24** And what's your reward for completing that block-pushing nightmare? ''Spirals'', the ''very next level'', is one of the most notoriously difficult. In case a maze filled with ever-increasing numbers of random walkers wasn't bad enough, some Microsoft versions of Chip's Challenge have a [[https://wiki.bitbusters.club/Spirals_corruption corrupt level file]], making the level ''nearly'' UnintentionallyUnwinnable.
25** Level 89, ''Block Buster''. The blocks that are replicated by the clone buttons are ''very'' difficult to dodge in the Windows version due to a [[GameBreakingBug glitch]] that causes them to move erratically instead of remaining at a constant speed. And since Chip is a OneHitPointWonder, he must ''never'' fail at dodging any of them.
26** Level 91, ''Jumping Swarm''. Like ''Spirals'', another level notorious for its large numbers of randomly moving walkers.
27** Level 105, ''Short Circuit''. A nasty maze of chip sockets and recessed walls, which forces you to memorize the layout of the maze.
28** Level 131, the aptly titled ''Totally Unfair'', which requires you to memorize the layout of a previous level, titled ''Totally Fair'', and do the puzzle part of it while effectively blind.
29** Level 134, ''Pain''. Takes over 13 minutes even in the best attempt where you know what you're doing and make no mistakes. Beyond that, it's ExactlyWhatItSaysOnTheTin.
30** 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.
31** Level 140, ''Icedeath''. Solving this level without a map is nearly impossible, as sliding even once in the wrong direction results in death, and [[FakeDifficulty you can't see whether a given direction is safe until it's too late]]. It takes over 60 slides to reach the skates. Have fun.
32** Level 147, ''Force Field''. Mazes alone can be difficult to tackle, but this one consists of force floors that hugely increase the difficulty level. The player has to frequently overcome their motion directions to make his/her way to the chips needed to obtain the suction boots and walk directly to the exit.
33** This is '''without''' getting into the [[FanSequel Fan Sequels]].
34*** [=CCLP2=] has levels that rely on unintuitive tile placements and a bigger focus on booby traps and random-working hazards and enemies, resulting in levels like ''Block Away!'', ''Exit Chip'' and ''Blocked Trap'' where it's almost impossible to foresee a deadly trap on the first attempt. This reaches its zenith (nadir for the less experienced players) with the 93th level, ''Exit Chip'', which does a ''deliberate'' attempt to troll players in every possible opportunity. Even then, there are more traditional levels that are still infamous for their difficulty, such as ''Mazed In'' ([[SchizophrenicDifficulty which for some reason is put as the 12th level]]), ''Warehouse II'', ''Keep Trying'', the two ''Oracle'' levels and ''Cloner's Maze''.
35*** [=CCLP3=], despite eliminating the unintuitive and debug-like elements from its predecessor, has its second half often regarded as '''nothing''' but That One Level back to back to back to back [[OverlyLongGag to back to back]], partly because of their notorious MoonLogicPuzzle nature. Special mention goes to ''You Can't Teach an Old Frog New Tricks'' ([=CCLP3=] 144) for being harder than the already ridiculously difficult levels surrounding it. Solving it requires setting up no less than 5 rooms ''flawlessly'' so that one tooth monster can navigate through them in sequence to release Chip from a trap, so said tooth monster can control a toggle switch and then be trapped on ice so Chip can walk to the exit. Interestingly, in playing back the solution in Tile World, the focus switches to that of the tooth monster when Chip enters the trap. And like all fan-made level packs with more than 144 levels, [=CCLP3=] treats this one as a DiscOneFinalDungeon only, so you'll still have to tackle five more levels, including the formidable duo ''Suspended Animation'' (146) and ''Avalanche'' (147).
36*** Though not as vicious as their counterparts from previous sets, the later levels of [=CCLP4=] can catch unprepared players off-guard, as they rely less on out-of-the-box thinking like those of [=CCLP3=] (and never on the devious tricks seen in [=CCLP2=]) and more on multi-layered puzzles and compositions (meaning that you'll often see elements that seem useless at first, but come into play later), and occasionally on difficult instances of dodging or redirecting enemies. Good luck conquering levels like ''The Longest Track'', ''Paradigm Shift'', ''Japanese Game Show'' and ''Gimmick Isle''.
37** Chuck is certainly aware of the infamous nature of some of these levels and provided achievements in the Steam release just for beating them. These include the previously mentioned Blobnet, On The Rocks, The Last Laugh, Rink, Cityblock, Jumping Swarm, Totally Unfair, Blobdance, Icedeath and Force Field.
38** The sequel has no shortage of these, due in large part to being a massive SequelDifficultySpike:
39*** "Crazy", with lots and lots and lots and lots of sliding block puzzles in ''very'' tight quarters. The only saving graces you get are that there's no official time limit and if you just want to beat the level you only have to complete four of the puzzles to proceed (and you can pick and choose which ones you want to complete). If you're looking for a high score, though, you have to complete ''all'' 26 of them with no mistakes, while racing against a logic gate timer that locks you out of some multiplier flags after 10 minutes. [[spoiler:Even worse, you have to do it ''twice'', since a different version shows up as the final level.]]
40*** "The Village", which involves navigating around a dozen Chip clones through a series of obstacles, with the ultimate goal of freeing the real Chip from a trap so he can reach the exit. The difficulty lies in the fact that there's no obvious order in which to complete each task, and the goals are often set up in such a way that they require sacrificing the Chip clone involved once it's done. Because all of the Chip clones move at the same time, even one mistake can cost you a valuable clone, and more often than not it will require you to start the entire level over again.
41* UnderusedGameMechanic:
42** There is exactly ''one'' speed boot in the official ''Chip's Challenge 2'' campaign, and only during a demonstration of how monsters can snatch blue keys.
43** The hook, which allows you to pull blocks in addition to pushing them, appears in two levels: Flea Market and Line and Sinker. (It's never even mentioned in any of the lesson levels.) Thankfully, the levels it appears in at least make proper use of it as a gimmick.
44** Worse is the "bribe", an item that can be sacrificed when walking over thieves to prevent them from stealing any of your other items or halving your bonus score. It's given a proper introduction in Lesson 6, but goes on to be used just once for a very brief lock-and-key scenario in Flea Market (and a cheap way to limit your inventory to three items) and once to preserve the score granted from some optional bonus flags in Line and Sinker.

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