* SugarWiki/AwesomeMusic: [[https://m.youtube.com/watch?v=rdOQzN2GUHk A Strange Reunion]], which plays during the final fight with Clockwerk. It evokes the tense duel between two rivals while still managing to sound epic.
* BestBossEver:
** Mz. Ruby, for those who didn't find her to be ThatOneBoss. It's an UnexpectedGameplayChange to a rhythm game mixed with Simon Says. For those who were good with ''VideoGame/SpaceChannel5'', it provides to be a fun challenge. On top of that, Mz. Ruby also gives visual cues for those who are hard of hearing.
** The Panda King is basically a standard BossBattle... which is ''exactly'' why he's a fun boss. Every other boss has a gimmick of either outlasting their invulnerable mode, [[PuzzleBoss reflecting light to hit them]], or UnexpectedGameplayChange segments. The Panda King doesn't have any of these gimmicks.
** Clockwerk, for giving the player quite the challenge by testing their skills throughout the game, while still being a reasonably fair fight, plus the awesomeness of the setting; Sly’s wearing a jetpack to have an aerial dogfight over a volcano.
* BreatherBoss: While each previous bosses all required a specific strategy to beat them, the Panda King is nothing short of a walk in the park. His attacks are all slow, blatantly telegraphed (not that that's a bad thing) and easy to avoid. And what do you have to do to beat him? Avoid his attacks while approaching him, then whale away on him with your cane. No other boss had you do this. At all.
* BreatherLevel: Fire in the Sky, while still moderately challenging, is probably the easiest part of the game and a relieving change of pace before you're thrown into the brutality of Clockwerk's lair, and the Panda King is a refreshingly easy boss as the cherry on top. The only truly difficult part is the Murray race, and even that’s more forgiving than the previous one.
** Justified as this episode was meant to be the first, before switching places with Tide of Terror near the end of production.
* CompleteMonster: "[[Recap/SlyCooperAndTheThieviusRaccoonusMission01TideOfTerror Tide of Terror]]": [[StarterVillain Sir Raleigh]] of the Fiendish Five differs from his compatriots through his complete lack of any redeeming qualities or FreudianExcuse. Nothing more than [[AristocratsAreEvil a pampered aristocrat]] who became bored with his own rich lifestyle, Raleigh turned to piracy [[ForTheEvulz to amuse himself]]--and found it suited his tastes. The team's [[GadgeteerGenius machinist]], Raleigh invents a storm machine that sinks dozens of populated cargo ships and aircraft, leaving no survivors as Raleigh takes both the loot and the ruined vessels themselves as macabre trophies. He has no hesitation threatening to flog his minions for "an entire fortnight!" for their sloppy performances, either, boasting that if it wasn't for their negligence he could have sunken "a hundred ships by now!"
* DemonicSpiders: All of the flashlight guards count as these, but Muggshot’s Doberman Pinschers are particularly nasty since they come ''sprinting'' at Sly much faster than the other guards if they spot him, but while the other guards fire single projectiles that can be dodged with some skill, Muggshot’s fire a barrage of 4 shots that all home in on Sly. If any bullet hits him, you’re done.
** [[ShapedLikeItself The spiders]] from Vicious Voodoo are some of the few enemies that appear during stealth sections and can easily interrupt the flow of the gameplay if the player is unaware of their locations. While they can be dealt with in a single cane swipe, the game likes throwing lots of spiders in cramped areas.
* DisappointingLastLevel: Various minigames start replacing platforming levels later in the game. This culminates in Clockwerk's lair, which has no hub world and consists mostly of [[GimmickLevel gimmick levels]] - out of 7 missions, only 2 are full platforming levels. Even the FinalBoss is a glorified turret section with minor platforming elements, [[Administrivia/TropesAreNotBad although it still manages to live up to the hype]].
* GoddamnedBats:
** The ghost rats from the Vicious Voodoo episode, due to coming from [[MookMaker infinite supplying gravestones]].
** The bomb toting roosters from the "Down Home Cooking" level.
* HilariousInHindsight: The game introduced us to Panda King, who practices kung-fu and uses fireworks. Six years later, [[WesternAnimation/KungFuPanda1 a movie about a certain panda who practices kung-fu and uses fireworks came out.]] The [[WesternAnimation/KungFuPanda2 sequel]] makes it even more hilarious.
* JerkassWoobie: Muggshot, Mz. Ruby, and Panda King of the Fiendish Five could qualify, [[FreudianExcuse all being rejected/bullied in their youth and becoming criminals to get revenge]]. Raleigh is a notable aversion, as [[AristocratsAreEvil he was well off]] and [[ForTheEvulz became a villain out of sheer boredom]].
* MoralEventHorizon: Clockwerk definitely crossed it when he had the Fiendish Five kill Sly's father, [[spoiler:but it turns out that his whole reason for it? He hates the Cooper line and wants to surpass their reputation.]]
* {{Narm}}:
** When Carmelita is temporarily defeated again in Fire in the Sky, when the rock she’s falling on falls, [[SpecialEffectsFailure she stands stiff as a plank on it as it]] ''[[SpecialEffectsFailure slowly]]'' [[SpecialEffectsFailure sinks into the snow, creating an unintentionally comical sight in what should be a tense scene.]]
** The [[FinalBoss Clockwerk fight]] has as much tension as the rest of the level, with Sly maneuvering over mechanical parts in a volcano and avoiding lasers to get to Clockwerk while dramatic music blares. However, the final part of the fight has a few details that somewhat detract from the atmosphere, namely that the malfunctioning Clockwerk starts spouting silly non sequiturs while repairing himself and the fact that him falling into the lava makes the sound effect for splashing into water.
* NarmCharm: As mentioned above, Clockwerk suddenly spouting nonsensical, even silly phrases while he's malfunctioning can take you out of his fight's atmosphere... but at the same time, they can make it even creepier thanks to the [[WordSaladHorror juxtaposition of the nonsensical dialogue and his hellish voice truly making him feel like a deteriorating machine.]] Depending on how one interprets his dialogue, phrases like "Feet together" and "-been selling flowers" may not even be nonsense, but ''his life flashing before his eyes''.
* ParanoiaFuel: [[spoiler:Mz. Ruby is the only one besides Clockwerk to know precisely who is messing around in her base of operations.]]
* PortingDisaster:
** The [=PS3=] remaster remixes some of the music - while this doesn't sound too bad on it's own, it does result in certain musical cues to play way earlier than they should (and in some cases, certain songs won't properly play at all). It's annoying enough as is in the intro and "A Strange Reunion", but it's absolutely ''fatal'' in "A Deadly Dance", since the song is completely desynced from Mz. Ruby's inputs.
** Downplayed with the Vita port, which removes the developer commentaries, probably to save space.
* ScrappyMechanic: Unlike in some other platforming games with optional time trials in each level, you actually lose a life if you die after you start the timer. Especially bad since the game takes away your horseshoes if you trigger the timer, so not only are you reduced into a OneHitWonder, the difficulty will likely drain your extra lives like all hell. While fortunately the only penalty for losing all your lives is that the game ignores your latest checkpoint and sends you to the start of the level instead, it's still rather annoying.
* ThatOneAchievement: Those damned Master Thief Sprint challenges. They get a little easier once you get the hang of it, but quite a few of them can only be beaten by [[LuckBasedMission pure luck and timing]].
* ThatOneBoss:
** Mz. Ruby, as the fight against her is an UnexpectedGameplayChange to a rhythm game, becoming strangely similar to ''VideoGame/SpaceChannel5''. Your sense of timing has to be ''very'' precise to land some of those button prompts as well. Doesn't help that in the [=PS3=] Collection, the rhythm that you have to press the buttons in is off beat from the song. It can really annoy some of the more musically inclined players.
** Muggshot as well, mostly because you have to have amazing dodging skills in order to evade his bullets, and Muggshot is a pretty fast mover. To make matters worse, the second floor is oddly shaped with a few pitfalls and the last phase of the boss has you spire jumping to turn the mirrors around. Oh, and if you use a mirror as cover that’s been turned to face him, it’ll turn away when he goes to shoot you. There is one [[EasyLevelTrick saving grace]]; while using the roll move, Muggshot is completely unable to hurt you.
* ThatOneLevel:
** "A Ghastly Voyage", in large part due to the dozens of obstacles you have to shoot through to advance, not to mention all the GoddamnedBats.
** "Sinking Peril". Remember that Daredevil Comet mission from ''VideoGame/SuperMarioGalaxy'' where you have to rush through Melty Molten Galaxy without getting hit? Yeah, it’s like that, but with a lot more climbing and precision jumping required. There are also portions of the level (electrified gates) that you can't rush through—you ''have'' to wait for the electricity to stop firing before you can pass.
** "Bentley Comes Through," because every broken piece of code hurts you AND you have OneHitKill security drones after you as well. It eventually gets to ridiculous NintendoHard levels.
** Both of the Murray races are among the most frustrating parts of the game, due in part to the loose physics of the car and the tight track design making it a huge pain to even pass up the other cars, much less hold the lead. At times, they can really feel like a LuckBasedMission. To add insult to injury, finishing them is mandatory to beat the game.
** Piranha Lake isn’t particularly hard compared to the rest of the game, but it can be a serious slog to beat for newcomers. You have to light up 25 torches while using piranhas to fuel your swamp skiff’s flamethrower. Catch is, you’re given a very tight 2 minute time limit, and the piranhas constantly flee from you and have tiny hitboxes, making it hard to stack up on fuel. Oh, and you can only hold five shots at any time.
* TheyWastedAPerfectlyGoodCharacter:
** Sure, all five members of the Fiendish Five are extremely colorful and memorable in their own unique ways, but it would have been ''really'' awesome to see them all being dastardly as a group. Sadly, aside from a single flashback to [[DeathByOriginStory the death of Sly’s father]] (where we just see their silhouettes), they spend the whole game in their separate lairs.
** Unlike the later games, the villains don't have almost any screentime before their fights, which means they don't get too much characterization as a result. You ''can'' piece some details together from their PA announcements and intro cutscenes, but they don't feel as fleshed out as, say, Don Octavio or Contessa.
* UnderusedGameMechanic: Sly has the ability to hide in barrels to avoid projectiles when activated by a pressure-sensitive rug. Problem is however is this mechanic only appears in two levels: A Cunning Disguise and A Daring Rescue.
* ValuesDissonance: [[MsFanservice Carmelita Fox]] is constantly objectified in the post mission newspaper stories. Which is somewhat balanced out by her actually being a very effective police officer.
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