A while back, my fiancee and I learned that Tails was originally supposed to be the keeper of the Master Emerald, not Knuckles. In Sonic 2 on the Sega Genesis, they were working on Wood Zone, and Hidden Palace Zone, where Tails would be found.

While on Sonic's run, you'd play through the game like many of us remember. With Tails, you would get Wood Zone where Sonic get's Metropolis Zone, 3 other zones and Hidden Palace Zone.

After learning about this, I downloaded a Sonic 2 ROM, and busted it wide open with a ROM Hacking utility, where I found these mysterious zones. They don't play properly when forced to be a playable zone, but they're in there. Only Wood Zone and Hidden Palace Zone know their names when launched. The other zones do not.

Anyway, this is my "What If..." Drawing of that. Tails here is a bit more mature looking because I thought this job would be for someone older than Tails. So... here ya go. I do like this Tails, I may do more mature Tails fan art.

Tails (C) SEGA/Sonic Team