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In the Video Games
Yasushi Yamaguchi designed Tails for an internal competition for the sidekick. His entry won, but his character's name was changed from "Miles" to "Tails". Yasushi then sneaked the name "Miles" into the character's name as his legal name; "Tails" would be his nickname. Yasushi ended up with a compromise.
Miles was first seen on Sonic 2 for the Master System but made his first hit in Sonic 2 for the Megadrive where he played the part of Sonic's sidekick and also as a playable charecter. Unfortunately, he could not be made to fly at this point- but this changed first in Sonic and Tails, and then in Sonic 3 when he made his second major appearance. This was a big step forward for Miles and he got much more well known and respected at this point.
In the games, Tails first appeared as a big fan of Sonic's, who began following him after being rescued by the hedgehog. After following his hero relentlessly for a long time, Tails eventually became fast enough to keep up with Sonic by spinning his two tails like a propeller. Although he can fly like a helicopter, he also enjoys flying Sonic's red biplane, the Tornado. As the series progressed, it was obvious his interest in the old biplane went farther than just piloting it- Tails is a mechanical genius with an intellingence comparable to Dr. Eggman's, and soon after, many modifications to the Tornado, as well as new biplanes, were added to his arsenal. He also operates a small blue submarine called the 'Sea Fox' and a F1 racer called the 'Cyclone'.
In Sonic Adventure 2 Tails uses a third incarnation of the Tornado, a half-plane half-mecha machine (think Macross/Robotech) called the Tornado II, to attack, rather than his own strength, an arguably much more effective (and destructive) method.
Just like many of the people who hang around Sonic, Tails can do the Sonic Spin and the Spin Dash, as well as attack with his tails by twirling around. He can also use Thundershoot, whereby he electrically charges Sonic and Knuckles and hurles them at his enemies. He can also swim quite well, something Sonic has never learned to do.
Tails can't transform with the seven Chaos Emeralds like Sonic, Knuckles and Shadow can. However, Tails DOES transform into Super Tails if he gains the power of the 7 Super Emeralds, which are powerful incarnations of the Chaos Emeralds when exposed to the Master Emerald.
Miles has started to grow up and become more independent, but he can still be found at Sonic's side whenever the world's in need of the Sonic Heroes...
Comics and Tv shows
Tails has appeared in several cartoon shows, such as SATAM, Adventures of Sonic the Hedgehog, and Sonic X. (He is absent from Sonic Underground, however)
He also appears in Sonic the Comic and the Archie Sonic Comics where he is developed upon as the Chosen one and the son of Rosemary and Amadeus Prower. In the Archie Sonic comic he seemed to has lost his parents at an early age, and admired the Freedom Fighters Particularly Sonic. He's grown pretty close with the Princess Sally calling her Aunt Sally and feeling Sonic's like his big brother. Jules and Bernie hedgehog (Sonic's parents in the comic version) also veiw Tails as a son to them and lastly Mina Mongoose has been making an impact too. While he's by no means romantically interested in Mina he certainly does enjoy her company and likes her singing. When absorbing 50 rings and 7 chaos emeralds he becomes Turbo Tails where he goes from orange to dark orange, all natural abilities upgraded and he is like super Sonic immune to all attacks that come his way. However there is an even more advanced form of the young fox. Hyper Tails after absorbing large quantities of chaos energy. When Tails turns into Turbo Tails you'll notice his orange fur turns brown and is aided by 4 flickies that have chaos energy and will destroy whatever he wishes them to.
Recently (or not so recently, just more popular now) allegations of a Tails-Amy relationship have appeared. This may be touched upon by the TV series, or it may simply never be expanded upon. The same goes for the possible Tails-Fiona fox relationship that could be present in the comic.
Tails has appeared in the following games: