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Pilotwings is a flight simulator franchise created by Nintendo for the Super Nintendo, Nintendo 64 and Nintendo 3DS. The game was developed by Nintendo's Entertainment Analysis and Development division (led by Shigeru Miyamoto), and was first released in 1990 in Japan and 1991 in the United States. The European release followed in 1992.

The games feature several training missions and lessons that players must complete in order to earn pilot licenses, using several different vehicles (including a plane, hang glider, rocket belt, as well as skydiving and other secret unlockable vehicles). Players are graded based on a number of different factors, including checkpoints cleared, accuracy, time spent and completion of required (or additional) tasks. Some missions also have bonus stages that can be cleared for extra points.

Pilotwings was well-received upon its release due to its overall graphical presentation and gameplay style. In 1996, Pilotwings 64 was released as a launch title for the Nintendo 64, featuring sharper graphics, more areas to explore and a variety of bonus games. In 2011, Nintendo also released Pilotwings Resort for the handheld Nintendo 3DS.

Interestingly, all three games in the series have been developed by separate companies. As mentioned before, Nintendo EAD made the first game. Paradigm Entertainment, who already made video simulation, helped with 64. Monster Games, who specializes in racing games, lent a hand with Resort.

Tropes used in Pilotwings include:
  • Anime Hair: Lark and Goose. Lark merely has some extremely messy bangs under his Nice Hat/helmet, whereas Goose hides tall, gravity-defying hair under his helmet.
  • Badass Mustache: Hawk from 64. Ditto for Meca Hawk.
  • Bare Your Midriff: Ibis and Robin both feature this in their civilian attire.
  • Boobs of Steel: In a sense, Robin. As the heavy class female, she is accordingly stacked.
  • Bragging Rights Reward: The Birdman outfit in 64, which is only available at the very end of the game and allows you to travel around without crashing or needing to use fuel.
  • Collection Sidequest: The Birdman stars in 64.
    • The free flight mode in Resort includes this. "i" rings, balloons, rings, and trophies are scattered throughout Wuhu Island.
  • Character Select Forcing: Present, but only lightly Enforced Trope. In 64, each class of pilot works best with a specific vehicle (Light = Rocket Belt, Medium = Hang Glider, Heavy = Gyrocopter). While it's not impossible to do well, by say, placing Lark (the lightweight male pilot) in a Gyrocopter, matching up the right character with the right vehicle does make it a fair bit easier.
  • Cheerful Child: Both Lark and Kiwi, but moreso Kiwi.
  • Continuity Nod: Your reward for three-starring every mission in Resort is, Meca Hawk making a surprise reappearance. He can be found circling Wedge Island, with a "i" ring above him. His facts state he's mellowed out, and isn't bent for destruction. He even screams if you crash into him!
  • Cool Shades/Sunglasses at Night: Goose, the mediumweight male pilot in 64, and Big Al in the original.
  • Eagle Land: Goose and Robin from 64 are very American in their designs, from their blond hair to the predominant use of red, white, and blue colors on their casual attire (this is combined with stars and stripes for their flight suits).
  • Easter Egg: See "Rushmore Refacement" below.
  • Efficient Displacement: Your character will leave a human-shaped silhouette in the ground if you go skydiving without opening your parachute in the original game.
  • Evil Knockoff: Meca Hawk to Hawk. No longer evil after he chills out.
  • Featureless Protagonist: The player character in the original... up until the end credits. Dark hair, male, looks to be in his 20's, with about as much Japanese as Big Al.
    • Averted in the later games. 64 has six individual people you can play as. Resort features a Mii of the player's choice.
  • Fictional Country: The Little States island is a miniature, but very convincing replica of The United States.
  • Five-Man Band:
  • Fun with Acronyms: The E.V.I.L. Syndicate.
  • Getting Crap Past the Radar: Robin's name in the Japanese version of 64 is "Hooter". Localizers apparently thought the joke wasn't too funny.
  • The Ghost: The Mad Scientist responsible for Meca Hawk's creation.
  • Have a Nice Death: The many snarky comments by the trainers upon failing an event.
  • Hollywood Darkness: Both played with and averted in the original. Area 7 takes place at dusk, but the visibility is still clear. Area 8 and the final helicopter mission, by contrast, are in near-pitch darkness.
  • Humongous Mecha: 64 had a mission where you fought a giant robot version of Hawk, named Meca Hawk. As mentioned above, he'll come to Wuhu Island after beating the game. Since he's chilled out, he won't fight you this time.
  • It's Up to You: When your instructors are kidnapped by E.V.I.L, Al loads you into a helicopter to rescue them solo.
  • Large and In Charge: Big Al.
  • Lonely Piano Piece: The "Event Failed" music, which is a Dark Reprise of the "Event Clear" music.
  • Ms. Fanservice: Robin from 64, who doubles as Foreign Fanservice. She's designed with an American motive (blond-haired, blue-eyed babe; primarily red, white, and blue colors and a purposefully placed star on her left breast). She's wasp-waisted, very buxom, and hips to match. Her bio in the game manual shows her giving a flirty wink and selecting her as your pilot elicits a very sensual-sounding "Ohhhh yeah!"
  • Musical Nod: The hang gliding music in Pilotwings Resort contains snippets of its counterpart from Pilotwings 64.
  • Nintendo Hard: Particularly the chopper missions.
  • No Name Given: The character in the original. Also, the flight instructor in Resort.
  • Not So Stoic: Al is moved to tears if you manage to impress him. Does it happen that rarely?
  • Opaque Lenses: Big Al glares at you from behind aviator sunglasses.
  • Pass Through the Rings: One of the oldest examples of the trope; the original game was one of the (if not the) first video games to use this type of system.
  • Remixed Level: After completing all five missions, you're paraded through them again. The weather conditions have changed, and the difficulty is ramped up.
  • Rushmore Refacement: In Pilotwings 64, one level allows you to shoot a rockface of Mario carved into the side of Mount Rushmore, which changes it into Wario's face. Crashing into also yields the same result, and doing so for a second time would change the visage back to that of Mario's.
  • Scenery Porn: Half the fun of the entire franchise is cruising around looking at the backgrounds and islands.
  • Shiny Midnight Black: Ibis.
  • Spear Counterpart/Distaff Counterpart: The cast of 64 could be considered as such.
  • Spiritual Sequel: Pilotwings Resort seems to be one for Wii Sports Resort, oddly enough.
  • Statuesque Stunner: Ibis is tall and lanky, just like her male counterpart Goose.
  • Tech Demo Game: The entire franchise could be considered an example of this. The original game was mostly used to demonstrate the Mode 7 capabilities of the Super Nintendo, and was one of the first games to be released for the console, while Pilotwings 64 was one of the launch titles for the Nintendo 64. Pilotwings Resort is also a launch title, carrying on in the tradition of the franchise.
  • Theme Naming: All the pilots in 64 are named after birds. In order: Lark, Kiwi, Goose, Ibis, Hawk, and Robin.
  • Timed Mission: Every mission must be completed within a certain time limit in order to get the best score/move on to the next stage.
  • Unexpected Gameplay Change: The original game throws this curveball midway through; it starts out with simple training exercises on various aircraft, then turns into an action game where you have to avoid anti-aircraft fire in a helicopter to rescue your instructors.
  • Vector Game: Used in the original game on the apparatus selection screen.
  • What Could Have Been: A Pilotwings game was planned for the Game Cube in 2003, and was to be produced by Factor 5. Instead, the game was delayed, eventually resumed development on the Wii, but Shigeru Miyamoto delayed it indefinitely because of concerns that it wasn't good enough. Whether that game will ever be released remains to be seen.
  • X Meets Y: Pilotwings Resort is Pilotwings meets Wii Sports Resort.