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1* AngstWhatAngst: Tony, Shirley and Lance all surely don't sound worse from wear during the ''Expert'' levels of the original game. Keep in mind that this happens right after all of them were taken hostage by a terrorist syndicate.
2* SugarWiki/AwesomeMusic: "[[https://www.youtube.com/watch?v=OXqAbNqhZuk Birdman]]", the music for the Free Flight mode in ''64'', is perhaps the most well-known song in all three ''Pilotwings'' installments. Even original composer Dan Hess is very fond of it, especially because it got to be one of the longest tracks in the game.
3* [[Awesome/VideoGameLevels Best Level Ever]]:
4** Little States in ''64''. It is, as the title indicates, a miniature version of the lower 48 U.S. states, and is the biggest map in the entire game. It's easy enough to just ignore your objective and [[SceneryPorn go explore for a while]]. Considering the system the game is on, being able to cram together such a map without resorting to mid-level loading zones is pretty damn impressive.
5** Birdman in ''64''. Not only is it a reward for getting gold medals, but it's a calm, relaxing flight through a level, with calm, beautiful music and picture taking.
6* BigLippedAlligatorMoment:
7** The helicopter rescue missions in the SNES original. Why are your instructors being held captive in a war zone? Who cares, go blow stuff up!
8** The Bonus Chance minigames count too. A penguin diving into a pool? A man in a bird wing costume leaping out over the sea? It's especially jarring if you need the minigame's bonus points to skim by on a course thanks to doing too poorly, meaning these BLAM moments in an otherwise down-to-earth title are ''essential'' to progression.
9* CrossesTheLineTwice: Crashing, particularly in ''64'' where your pilots have cartoonishly hilarious screams.
10* NightmareFuel:
11** Some of the instructor's surprised facial expressions when you get a perfect score in the SNES original -- ''especially'' Shirley, who gets [[UnintentionalUncannyValley bizarre vertical line-shaped eyes that just don't look right on an otherwise relatively realistic-looking human]].
12** The helicopter missions in the SNES version. You suddenly go from lighthearted pilot training to ''crossing a combat zone'' in order to rescue your instructors or Big Al's brother. If you get hit, you're treated to the helpless sequence of your chopper spiraling downward before crashing into the ground, and instead of the usual [[HaveANiceDeath post-failure banter from your instructor]] with the opportunity to try again, [[NonStandardGameOver you just go straight to the game over screen]]. Combined with your crash being in enemy territory, the implication is that you didn't just fail at your objective, you ''died''.
13** Similarly, Meca Hawk's appearance in ''64'', in a game that's otherwise free of any hostile entities. After going through dozen rings, blowing up stationary targets, taking pictures, and landing on floating pads, you now have to enter combat against a giant humanoid who throws rocks at you, and yes, being hit can potentially end the mission as your Gyrocopter goes spiraling down into a crash.
14** Also from ''64'', there's the Holiday Island nighttime EasterEgg. If you fly into the sewer tunnel, you hear a very eerie droning noise and it suddenly turns nighttime outside. To make matters worse, the game pauses for a second when this happens, so you'll likely lose control and either crash into the water or the walls ([[MortonsFork and then into the water]])... and that's ''with'' the Rocket Belt, because you are not getting out of the sewer tunnel alive in a Hang Glider or Gyrocopter.
15** Playing as Kiwi or Robin in ''64'' and crashing with either the Hang Glider or Gyrocopter will treat you to very unsettling facial expressions from the lady in question in addition to the usual screams. They will also scream like hell when flying through flames (such as the Ever-Frost Island smokestack or the Statue of Liberty torch on Little States), although they don't take any actual damage.
16** Crashing while playing as Birdman in ''64'' will net you a piercing scream and eerie music.
17* NintendoHard: The original game in particular is very realistic for its time, making the simple act of [[PassThroughTheRings going through rings]] or even just landing correctly rather difficult.
18* PolishedPort: The original version of ''64'', being limited by [[Platform/Nintendo64 its hardware]], ran at 30 FPS during gameplay, but the Platform/NintendoSwitch Online port runs at a much better-looking 60 FPS.
19* SpiritualSuccessor: ''Pilotwings Resort'' seems to be one for ''VideoGame/WiiSportsResort'', oddly enough. Specifically, it's mostly based on the Island Flyover mode from that game. In particular, Free Flight Mode is pretty much identical, just with more vehicles allowed.
20* ThatOneLevel:
21** The SNES version has the helicopter levels, which act as the finale for both the game's first act and the game as a whole. Not only is it an UnexpectedGameplayChange since you've never controlled the helicopter before, but it's the only kind of level where you have to shoot at anything using the helicopter's gun. And you're a OneHitPointWonder on top of that; thanks to the DarkerAndEdgier nature of the levels, it's implied that crashing actually kills you as opposed to being AmusingInjuries. Because of the sheer number of things on the ground that can shoot at you, including hidden bases that are camouflaged by the trees, the only way to play is by going to your objective very slowly, being extremely careful to pick off the targets one-by-one before landing to complete the mission. Even if you know what you're doing, these levels are going to take a while, simply because there's no way to play other than carefully that has any hope of clearing these stages.
22** In ''64'', Class A for the Hang Glider has the "Chicken Dive" mission. You start by jumping off the summit of one of the Ever-Frost Island mountains and follow a waterfall down to try to fly through as many rings as you can. Because diving causes you to pick up speed, it becomes easy to lose control of your Hang Glider. But the last few rings are right in front of a wall and you need to ''quickly'' pitch up and turn right to avoid a crash. Ignoring these "daredevil" rings is not optional if you want the perfect score.
23** Another perilous mission in ''64'' can be found in the Pilot Class in Rocket Belt, known as "Dark Cavern". You have to [[AirstrikeImpossible fly through a cavernous passage to the goal]]. There's a stream running throughout the cave, always putting you at risk of [[SuperDrowningSkills instant failure]], and bumping into walls takes away points. And you need to get through this cave without any collision-induced penalties in under ''two minutes'' for a perfect score. At least there's no landing component in this mission; when you reach the end, you just need to fly through the goal ring to finish. Also worth noting that when ''Magazine/NintendoPower'' was hosting content for this mission in the late [=90s=], recording your time was difficult due to the fact that you have about ''three seconds'' to photograph your time at the end before it disappears off the screen; at the time, non-Polaroid cameras did not show you the output of your shots and you had to take your film to a store later to get the photos processed. [[note]]However, [[CuttingTheKnot recording your play through a VCR could also work and cut out this issue]].[[/note]]
24* UglyCute: Missi the Monster in ''64''. She's a bright red, cartoonish river monster who emerges from the Little States's Mississippi River with the most obviously fake monster roar.

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