Board Thread:Questions and Answers/@comment-27168366-20160109214941/@comment-25622445-20160328150017

Well, there are two different versions of how Sonic met Tails, that, and then there's the 8-bit version, which just states that Tails is Sonic's best friend and has been kidnapped by Eggman for revenge due to his last defeat. But let's just focus on the Genesis/Mega Drive versions of the game, I'll dive into the Game Gear one later.

The Japanese manual states that Sonic just found a beautiful island to rest at, so he flew his plane down, Tails however was picked on by the residents of said-island for having two tails, and hence where the nickname "Tails" comes from, his real name being "Miles Prower". Tails is introverted, depressed, and melancholic, but one day he sees Sonic running, intrigued, he follows him, managing to keep up, Sonic regards Tails as nothing more than an irritating tag-along, but is impressed with his ability to keep up with him, lets him follow anyways. One day, Tails spots a beautiful plane just lying out in the open, which he marvels at, 'till Tails catches sight of the owner, Sonic, which he skulks away under the wing. Sonic is sleeping, 'till a huge explosion happens in the woods, the woods is on fire and a bunch of badniks are digging at the island, desperately searching for something, Sonic gets up, knows who did it, curses Eggman's name and runs headlong into the fire, Tails, in awe, could not help but follow, and over the course of the adventure the two become best friends.

That's the Japanese version, in the Western version, Tails is popular among the animals of said island, and has been a fan of Sonic's since he was born, he invented the spin dash, too, according to the Western continuity, following with the plot-line of the animal friends teaching Sonic all he knows. He meets Sonic, and the two team up against Dr. Robotnik to save the island.

That's the Western version, which hath been abandoned since the release of Sonic Adventure in the West, so if thou want to stick with the canon lore, one shalt stick with the Japanese version. Now we dig into the messy topic of the Game Gear games canon status. If the 8-bit version of Sonic 2 is canon, it must either be a midqual, or take sometime after the events of the Death Egg Saga, but the Game Gear games are of questionable canonicity, anyways, and I won't be delving into that.