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A training plane.
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[quote]What kind of aircraft needs 21 pilots?[/quote]
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Okay, hear me out; a Super-Megazord made up of 4 other Megazords!
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The Voltron Ferrets from Rick and Morty, Rick and Morty everyday, everyday Rick and Morty...
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Agent Vulpes
Guardian since August 5, 2020 || D1 & D2 - old
A pretty big one on a really long trip, I would guess. -
The closest I can come up with is the vehicle team Voltron which had 15, although I don't know if you would consider all of them "pilots" since not all were aerial vehicles. By all means, feel free to make as many dork jokes as you like for me knowing that.