"Lil' Buddy" (by Sonic), "Bud" (by Sonic),
"Mr. Tails (by Cream)",
Amelia Prower - Mother
Team Sonic
adventure, flying, swimming,
accomplishing stuff on his own
being picked on, thunder, ghosts
being interrupted while doing something important,
people underestimating him, people threatening his friends,
Bunnie Rabbot, Antoine D'Coolette, Rotor Walrus,
Amy Rose, Shadow the Hedgehog (to a degree), Rouge the Bat,
Cream the Rabbit, Charmy Bee, Espio the Chameleon,
Vector the Crocodile, Silver the Hedgehog, Blaze the Cat,
Colonel Robert Hogan, Johnny Austin
can pilot almost any kind of vehicle
Spin Dash
Flight
Swimming
I'm saying that if you open your heart, it’s gonna be all right! 
— Miles "Tails" Prower
Miles "Tails" Prower is the loyal sidekick of Sonic the Hedgehog. Like The Man himself, Tails isn't too far removed from his canon counterpart. However, there are some differences. Or, if you want to compare him with other individuals going by the same name, go here.
Backstory
ASMW
Born to unknown parents, Tails had nothing better to do than to run around Mobius, unaware that a mad scientist had taken over. One day, he saw Sonic the Hedgehog running around and decided to follow him around because he thought the Blue Blur was so cool. At first, Sonic got annoyed and wanted Tails to stop following him. However, when Tails started crying, Ol' Blue relented and let him tag along. It turned out to be a wise decision, too: Ever since then, they've become one of the most dynamic duos in video game history, not to mention two of the best Freedom Fighters in the Kingdom of Mobius.
AUTHOR'S NOTE: Certain readers may recall that Tails was treated like a kid in SatAM, unlike his appearance in the games. Well, here's an explanation: When Sonic & Tails first met up with Sally & the others, Sally thought Tails was too young to be going off on adventures and had him placed on probation. Naturally, Sonic disagreed, but after a huge argument, he relented. After a year, however, Sally took Tails off of probation.
Sonic Journeys
Born to Melvin & Amelia Prower, Tails was abandoned shortly after birth, leaving him with nothing better to do than to run around Mobius. One day, he saw Sonic the Hedgehog running around and decided to follow him around because he thought the Blue Blur was so cool. At first, Sonic got annoyed and wanted Tails to stop following him. However, when Tails started crying, Ol' Blue relented and let him tag along. It turned out to be a wise decision, too: Ever since then, they've become one of the most dynamic duos in video game history.
Sonic War Zone
Born to Melvin & Amelia Prower, Tails lived a normal childhood until age seven, when his family was kidnapped by Roseinian spies. Since then, he had been eking out a lonely existence, living off the land while conducting his own scientific research. Then, when the bombs started dropping on Emerald City, he took cover and waited for the whole thing to be over. He didn't have to take cover for too long, for he met an up-and-coming hero, a blue hedgehog who had also lost his family to war. The two formed an instant bond.
Personality
Tails' personality is unchanged, for the most part. However, he's not really that shy except maybe around strangers. Tails will rarely get angry, unless someone tries to hurt Sonic.
Appearance
Like Sonic, Tails' appearance has been the subject of much discussion. While all sources report seeing an orange fox with two tails, some have reported seeing a short fax with black irises and short limbs, while others have reported seeing a taller fox with blue eyes, longer limbs and a brighter shade of orange. In the Sonic Journeys series, Tails wears a tool belt and a pair of Scott goggles. In Sonic War Zone, he even wears a lab coat.
Abilities
Once again, Tails can fly using his two tails, and he can do all those other wondrous things that he could do in the games. He's also skilled using certain melee weapons. In You Can Choose, Tails is also shown to be particularly skilled with a submachine gun after enough practice.
Items & weapons
Unlike the games, Tails will sometimes carry a weapon around with him: A claw hammer. However, he may use firearms depending on the story. Tails is also very skilled with vehicles and owns a Tornado biplane.
Fanfictions
ASMW
Two Kinds of Heroes
Tails follows Sonic to Eggopolis on a mission to destroy one of Dr. Robotnik's mech factories. However, he – along with Sonic, Knuckles and the rest of the gang – get teleported to Stalag 13 during a freak electromagnetic storm. Unlike Sonic, Tails is eager to stay and help out Hogan with his mission, which is to blow up a factory that's going to produce the new E-75 heavy tank. First, he flies over to the factory and takes some pictures. Then, he starts building a teleporter device to get the Freedom Fighters back home, with Rotor & Kinchloe helping. Tails is also very eager to try out LeBeau's cooking and is impressed when Carter gives him some mint candies.
That night, Tails accompanies Sonic, Hogan, Bunnie, Newkirk & Carter to the tank factory. When the attack commences, Tails flies around and helps Sonic to draw the guards' fire. He witnesses Sonic get shot, but Sonic merely caught a bullet in his teeth, so he survives. Once the attack on the factory is complete, Tails and the rest of the Freedom Fighters go back home and destroy Robotnik's mech factory.
Tails also shows up in the "Sonic Says" segment, where Scratch & Grounder try to show him an unexploded hand grenade.
The Fakest Things Alive
At the start of the story, Tails is checking out a 1978 Yamaha YZ400 that Sonic brought to Knothole. Upon Sonic's request, he agrees to modify the bike, so Sonic goes to a junkyard to get some parts & scrap metal for him. However, Tails gets worried when Sonic doesn't return, and Silver's sudden appearance in Knothole confirms this. When Silver takes Tails & co. to the future, they learn that most of the world (save Eggopolis) has fallen into ruin without Sonic, so when they get back home, they have to find Sonic. To this end, Tails stays behind and guards Knothole while the others search for the Blue Blur. Eventually, they find him (actually, they found an impostor hedgehog), so the search is called off.
The next day, Tails finds out that Sonic (the impostor, actually) has left again). Furthermore, somebody's completely disassembled Sonic’s YZ400 and a laser cannon that Rotor was working on, so he has to hurry up and put the bike back together. By the time Tails is almost finished, Sally sends him out to find Sonic again. He finds what he thinks is Sonic (actually another impostor), but he gets tired and loses him, so he just goes back to assist Rotor with the laser cannon. Near the end of the story, Tails is helping Rotor shoot down stealthbots with the laser cannon when the real Sonic arrives and finishes off the rest of the stealthbots. Afterwards, Tails shows Sonic his newly-modified YZ400, which is faster, lighter, more efficient and better handling. It even gets a new paintjob & a name: The Whirlwind (not to be confused with the MTP-01 Whirlwind).
And Down Will Come Sonic – Cradle and All
In the beginning, Sally asks Tails if he's seen Sonic, but he hasn't. Later on, however, Tails ends up rescuing Sonic when his foot is injured. He appears in a few of Sonic's nightmares, too. When Sonic doesn't wake up, he gets a little worried, but doesn’t suspect anything until Sally tells him that Sonic's been poisoned. With Sonic's life in danger, Tails uses the Tornado 2 to fly to Azure Lake Zone and obtain the antidote. He's temporarily delayed by Amy & attacked by stealthbots, but he makes it back with the antidote. Once Sonic wakes up, Tails & the others give Sonic a group hug and travel with him to Eggopolis, where Dr. Robotnik has a new doomsday weapon built and ready to fire. After helping to destroy the weapon, Tails gets a bowl of mint candies from Sonic as a reward and returns the gesture with a hug.
Mighty Sonic
Tails helps to kick off the plot when he tells Sonic about a new show: Super Changin' Muscle Rangers (a thinly-veiled parody of Mighty Morphin' Power Rangers). Sonic hates the show, so he ends up struggling with Tails over the remote, which gets broken. As a result, Tails ends up watching the show by himself. Later on, he assists Sonic & the others in the rescue of the Muscle Rangers actors, piloting a Pterodactyl Vord. As a reward for rescuing them, he & Sonic get to guest star in an episode of Super Changin' Muscle Rangers, and he settles his differences with Sonic.
In the "Sonic Says" segment, Tails has been assigned to work with Shadow in science class, but he doesn't want to work with him because he thinks Shadow looks scary. However, Sonic assures him that looks aren't everything.
Other stories
Sonic Hotcakes
Having overheard Sonic's plan, Tails decides to bring Dr. Robotnik some hotcakes. He thanks Robotnik for helping him meet Sonic, but Robotnik gets angry when Tails gives him the hotcakes. Luckily, Tails flies away and meets up with Sonic outside of Eggopolis.
In this "Sonic Says", Tails gets a brand-new set of power tools for Christmas, which he really likes.
A Blue Light For the Dark
When Sonic returns home, Tails notices something wrong with him. However, the Blue Blur is oddly reticent in regards to this matter. Still, he thanks Tails for being there for him. At one point, Sonic accidentally yells at the Two-Tailed Wonder. Fortunately, he apologizes and avoids an argument. Because of this, Tails figures that if Sonic's not willing to talk with him, then he should go confront the source of his problems directly. Unfortunately, this also proves ineffective. In fact, it's only after Tails listens in on a conversation between Sonic & Rouge that he learns about what’s really eating his best friend. As per Rouge's suggestion, the two of them take a nostalgia trip around the world, finishing at Star Light Zone. Refreshed, Sonic goes out on his own, while Tails does maintenance on the Tornado.
Later in the story, Tails is shocked when Mephiles comes to Knothole with Sonic at his side. The two assure the little orange fox that the Dark One is good now. At first, Tails is unsure of whether to believe this, but after giving it some thought, he forgives Mephiles. At bedtime, Tails sees Mephiles in Sonic's bed, which leads him to believe that Sonic replaced him as a best friend. However, Ol' Blue assures Tails that he'll always be his best friend. To this end, Sonic & Tails move Tails' bed over next to Sonic's. Then, the three of them go to sleep, with Tails & Mephiles cuddling Sonic.
Sonic's Weird Birthday
Tails is happy to see Sonic return to Knothole. Then, his attention is grabbed by the 1970 Camaro that Sonic drove into Knothole, until Sally tells everybody to get the cake ready. When it's time to give the Blue Blur his gifts, Tails gives him a big case full of Super Putty adhesive, claiming to remember a time when Sonic asked for something like this. Even though Tails misremembered, he’s just glad that Sonic accepts the gift anyways. He's also happy to get a hug from his friend. After Ol' Blue sees the statue of him & Tails and asks if anyone will ever see it, the Two-Tailed Wonder assures him that people will see it someday. Near the end, when Sonic is in a trance, Tails holds up three fingers and asks his friend how many he’s holding up. However, he has to pull them away when Sonic mistakes them for fish.
In the "Sonic Says" segment for this episode, Tails flies Knuckles back to Angel Island in the Tornado when the latter is unable to take himself home.
A Dark Birthday
Tails informs Sonic that Uncle Chuck has terminal cancer. Later, Tails checks up on the Blue Blur after the funeral. When Alan Schmidt is telling him about Sonic inheriting Uncle Chuck's business, Tails is excited by the prospect of getting a new workshop. However, when Sonic tries to unload the business onto him, he declines. Nevertheless, he agrees to a new plan: he will get his own little workspace at the business. Here, he uses his time on a jetpack. While doing so, Rouge drops in and informs Tails that it's her birthday tomorrow as well as Shadow's, and she gives him a kiss on the cheek before flying away. When Sonic returns and frets over what to get for Shadow & Rouge, Tails assures him that he’ll find something and promises to chip in for the gifts.
When Sonic returns with an AK-47 for Shadow and a diamond for Rouge, Tails inspects the former, only to get a rude surprise: the rifle was made by a manufacturer known for producing poor-quality knockoffs. He then tells Sonic not to give the rifle to Shadow. Later, Tails watches – and unwillingly participates – when Sonic buys random gifts for Shadow & Rouge. At the end of the workday, he goes home, only to discover that one of the Tornadoes is missing. He then hears a whining in the distance, as if a plane is going to crash. Thus, he straps on his jetpack, fires it up and heads for the source of the sound, which turns out to be Sonic attempting suicide by plane crash. Tails struggles to keep the Tornado 1 from crashing, but in the end, he manages to land it safely. He gets mad at Sonic for what he tried to do, but then changes his tune when Sonic nearly breaks down. Tails then reminds him about more difficult situations he’s faced in the past where he came out on top, which placates him.
The next morning, as per Sonic's orders, Tails gets to work on Shadow & Rouge's gifts. They turn out to be a little late, but Shadow lets them live anyways. After Sonic & Tails' gifts – motocross bikes – are opened, Tails joins Sonic, Shadow and Rouge for a motocross race. Since he is only riding a 250cc machine, Sonic & Shadow easily get ahead of him. Later in the race, when Sonic & Shadow are making up, Tails gets a hug from Rouge.
In the "Sonic Says" segment for this story, Tails is hanging out with Cosmo in Hancock City. He is disappointed because the only birthday gift he could afford for her was a beat-up music box that he found in a dumpster. Fortunately, she likes the gift, and he gets a kiss.
Sonic Wave
In contrast to Sonic, Tails is more enthusiastic about the experiment that Mr. Obotir conducts in History class, even trying to reassure Sonic that they don't have to do it outside of class. However, when Obotir teaches the class about "Strength Through Community" on Day Two, christens the experiment "The Wave" and teaches the students the new salute, Tails is genuinely worried. However, he has no idea what to do about the movement until he falls asleep, whereupon he wakes up in the middle of the night and gets the idea to print anti-Wave leaflets.
While working on his leaflet in the school library, Tails is shocked when Silver shows up, though the latter is only looking for Blaze, so the Two-Tailed wonder continues his work unabated. After school, Tails is about to run around with Sonic when Amy and Cream show up. When they demonstrate their allegiance to The Wave, Tails is worried and tries to tell them about the importance of studying history. He is even more worried when a local gang leader who’s not even in school repeats the three mottoes of The Wave and does the salute before driving off. Back home, Tails prints up a few leaflets as part of a test run, but later that night, he is disappointed about the prospect of having to print revised leaflets based on Rouge's suggestions. Nevertheless, he agrees to it when Sonic agrees to get him more ink or toner for his printing press.
The next day, Tails is just as confused as Sonic when Rouge wakes them up early, until she explains that she's extending a special favor to both of them based on how good Sonic was to her last night. He is amazed when he finds out that Rouge cooked a large breakfast and asks how long it took her. After breakfast, Tails flies off to school with Sonic and Rouge, but is forced to take a brief detour when Sonic notices Silver by a tree. He tries to cheer Silver up by telling him about his plan, but is unsuccessful until Sonic gives a little speech. Tails then shows Silver one of the leaflets he printed up, and then assists Sonic, Rouge and Silver in spreading them around the school before class.
In class, Tails is discouraged when he finds about the widespread distribution of groups just like The Wave. When Knuckles and Shadow drag Sonic away for "disruptive" behavior, Tails tries to save him, only for Storm to stop him. At lunch, Tails tells Blaze about how The Wave felt wrong when he tried the initial exercises. When he, Sonic, Rouge and Silver stop at Mr. Obotir's house to try to convince him to stop The Wave, Tails explains that it's robbing students of free will, impacting academic performance and causing students to do things that they wouldn't otherwise do. He even cites the school's mission statement as being counter to the precepts of The Wave.
In spite of Mr. Obotir's willingness to keep going with The Wave, Tails has a backup plan to stop it if it keeps going. Later that night, Tails and Sonic host a pizza party at their house with Rouge and Silver. Fortunately, he survives the drive-by that occurs while he's working on his backup plan, but elects not to follow Sonic. After the police conclude the investigation of the shooting, Tails wonders where Silver will sleep when he chooses to stay for the night. Tails is uncomfortable sharing the bed with Sonic and Silver.
On Day Five, Tails meets up with Rouge and Silver for breakfast and plays hooky until it’s time for the rally at the school gym. Like his three compatriots, he disguises himself as a Wave member in order to get in. When he witnesses the grand spectacle of the rally, he is the first to comment on it. After being knocked out and captured, he finds out that Mr. Obotir is really Dr. Robotnik upon waking up and asks how he could do such a thing. After Robotnik leaves, Tails pretends to have an asthma attack upon Sonic's urging and frees his friends while taking out SWATbots. However, he remembers that he forgot Miles Electric at his house, where he is the first to notice a police car heading for the school.
After the police's initial failure to stop The Wave, Tails wonders how he and his friends will get back in the school. However, he is able to get back in when Sonic throws a soda can to distract the police. Inside, he helps to search for Robotnik, but also comes up with nothing, even questioning whether the Doctor is even still in the school. When Espio tells them that Robotnik is holed up in a secret maintenance room, Tails uses Miles Electric to start breaking the code that locks the secret door after Sonic fails to bust it open. Just as he cracks the code, however, he hears an explosion outside and follows Sonic to check it out.
Upon rendezvousing with Captain Davison, Lieutenant Robert Forrest and Sergeant Martin Hand, Tails assists his friends in explaining The Wave. When following his friends and S.W.A.T. Team 2 inside, he opens the secret door that he unlocked in order to let them in. After Rouge lets out a shriek to disorient Robotnik, Tails assists in destroying the EggRobos in the room. After helping to escort the Doctor to one of the A/V rooms, Tails watches as he – back in his Mr. Obotir disguise – tells the truth about The Wave. Tails then goes forwards with the final part of his plan: playing a graphic documentary about the aftermath of the Tedescan Civil War. After The Wave is finished, Tails explains to Captain Davison the real reason why Sonic characters go to school. After being surprised by the prospect of earning medals for his courage, Tails follows Sonic out of the school.