History YMMV / Pilotwings

* AccidentalNightmareFuel: 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]].

** 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.

** In ''64'', Class A for the Hang Glider has the "Chicken Dive" mission. You start by jumping off the summit of one of the Holiday 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.

* PolishedPort: The original version of ''64'', being limited by its hardware, ran at 30 FPS during gameplay, but the Nintendo Switch Online port runs at a much better-looking 60 FPS.

* AccidentalNightmareFuel: Some of the instructor's surprised facial expressions when you get a perfect score in the SNES original -- ''especially'' Shirley, who gets [[UncannyValley bizarre vertical line-shaped eyes that just don't look right on an otherwise relatively realistic-looking human]].

* UncannyValley: Some of [[https://www.spriters-resource.com/fullview/13140/?source=genre Shirley's facial expressions]] when you score well definitely qualify.

* UncannyValley: Some of Shirley's facial expressions when you score well definitely qualify.

** Crashing while playing as Birdman in ''64'' will net you a piecing scream and eerie music.

* FunnyAneurysmMoment: One choice of destination for the Nintendo Power August 1996 Player's Poll Contest grand prize winner was Washington, D.C., where Nintendo Power invited the winner to "hob-nob at the Capitol". 24½ years later, the term took on a sinister new meaning when the most devastating attack on U.S. soil this side of 9/11 took place at the Capitol, with some classifying the attack as domestic terrorism and right-wing people generally describing the attackers as all but hob-nobbing at the Capitol.

** 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]]. The implication is that you didn't just fail at your objective, you ''died''.

** If you crash in the helicopter missions in the SNES version -- whether by slamming the copter into the ground or getting shot, in itself a frightening experience since you, a civilian aviation student, go straight from training to ''crossing a war zone'' -- [[NothingIsScarier there's no post-failure remarks from any of your instructors; you just go straight to the game over sequence]]. The implication is that you didn't just fail at your objective, you ''died''.

* [[Awesome/VideoGameLevels Best Level Ever]]: 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.

* FunnyAneurysmMoment: One choice of destination for the Player's Poll Contest grand prize winner was Washington, D.C., where Nintendo Power invited the winner to "hob-nob at the Capitol". 24½ years later, the term took on a sinister new meaning when the most devastating attack on U.S. soil this side of 9/11 took place at the Capitol, with some classifying the attack as domestic terrorism and right-wing people generally describing the attackers as all but hob-nobbing at the Capitol.

** Similarly, Meca Hawk's apperance 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.
** In ''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.
** Kiwi and Robin have very unsettling facial expressions in the 64 Version after you crash with either the Hang Glider or Gyrocopter.

** Another one in ''64'' can be found in the Pilot Class in Rocket Belt, "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 a 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]]
* 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.

** Another one in ''64'' can be found in the Pilot Class in Rocket Belt, "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 a content for this mission, 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, and this was ''before'' the age of modern fast-shooting smartphone cameras.[[note]]However, [[CuttingTheKnot recording your play through a VCR could also work and cut out this issue]].[[/note]]

** Another one in ''64'' can be found in the Pilot Class in Rocket Belt, "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 a content for this mission, 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, and this was ''before'' the age of modern fast-shooting smartphone cameras.

** Another one in ''64'' can be found in the Pilot Class in Rocket Belt, "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 a content for this mission, 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.

** Another one in ''64'' can be found in the Pilot Class in Rocket Belt, "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.