Was Anakin always considered to be THE best starship pilot ever, or did another force user surpass him?
How about non force users? Who would be the best there?
Glad you asked! Afaik, Anakin was the best pilot in the galaxy. But, of course, Luke and Wedge and Biggs were also really good.
Han Solo and Poe Dameron are considered some of the best pilots in the Galaxy. There was this article released shortly before the publishing of "A Certain Point of View" that raised a question based on one of the short stories: Who's a better pilot, Hera or Han? And it fanboys over Han for the first half pretty well. Explains all the crazy things he's done, like getting through an asteroid field with impossible odds, and evading imperials over and over. Then he landed a ship straight out of lightspeed. And there's too many examples of things he's done in the EU. Even going as far back as the Marvel Comics from 1977, we see Han doing some crazy stuff.
Hera Syndulla in the nuCanon is also said to be a really good pilot. And so are the "aces" from the Colossus that we meet in Star Wars: Resistance. Those being Kazuda Xiono, Hype Fazon, Torra Doza, Freya Fenris, Griff Halloran, Bo Keevil, and Jarek Yeager. There's also the famous racer, Marcus Speedstar, who's Jarek's brother.
I think I also remember in Legends that there was this one short story from "Tales from the Mos Eisley Cantina" where we meet this other guy named "BoShek" who is force sensitive and actually beat Han's Kessel Run record, if you can believe that.
There's the entirety of Rogue and Wraith squadron, from the "X-Wing" series of books, in Legends.
In Canon, there's also the "TIE fighter" Comic which focuses on Shadow Wing, the best pilots the Empire has, and also the "Blade Squadron" short stories which focus on those who pilot the B-Wing, a ship that's known to be difficult to control.
There's honestly too many for me to name here, but those are just off the top of my head.
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