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Sonic R is about the capabilities of human achievement.
Compare the lyrics of Living in the City, "where everything is free" and Work It Out, where "nothing in this world comes for free". Clearly, we've got to put forth the effort to make life more liveable for everyone. Technology and innovation can help, but we've got to do our part and contribute to our world. We can't be Robotniks and have machines for everything, we've got to work ourselves like Sonic and company.
  • "Work it out. Think about it. You've got to make 'it' real."
  • "Where everything is free. Can't you see?"
  • Livin' In The City is more like "everything is free IF you can do the work." the song also includes the lines "You know you have to survive, you've got to keep the dream alive." That implies that things can only be free if you know how to help yourself to them, which means that, indeed, "Nothing in this world comes for free." "You have to make it what you want."

The Tails Doll is Mephiles
Before the Duke got him.

It was, in fact, Sega who written the Tails Doll creepypasta.
They had it in mind the whole time.

Alternatively to the above, Eggman is real, and he wrote the pasta.
He wrote it with the intents of scaring Sonic and co. into not wanting to foil his plan, then sent the Doll to vaporize them, which then accidentally created Modern Sonic's universe. This means Generations, Forces, and any other game featuring the Classic gang released after 1997 is non-canon.

In-universe, it's supposed to be Amy singing the songs.
Singing Voice Dissonance aside, at least three of the songsnote  sound almost like love songs (if they aren't outright, as some people say). Now, of all of the characters in the franchise, who is constantly chasing after a certain high-speed blue hedgehog, thinking they're in love (and in some cases, thinks they're "destined" to get married)?...

The soundtrack is about overcoming depression
Sounds very silly at first glance, but once you view it at angle, the pieces fall into place. The lyrics have a consistent theme of survival and persistence, and with the exception of Super Sonic Racing, the songs can tell such story this entry is stating:
  • Can You Feel the Sunshine: Someone is dealing with severe depression, and is trying to feel the sunshine, the light in the dark of their mental state ("Can you feel the sunshine? / Does it brighten up your day? / Don't you feel that sometimes / You just need to run away? / Reach out for the sunshine / Forget about the rain / Just think about the good times / And they will come back again…" and "When the sun goes down / I feel like I am waiting / For another day / When the clouds go away…").
  • Living in the City: Failing to have found the sunshine in their life, the person has contemplated suicide, with the singer talking them out of it, telling them there is so much to live for ("So many different things to see / There's no time / So many different things to do / But there's no time / So many people all around / So many feelings to be found / Living in a city where no one lets you down." and "In the sky at night / The stars are shinin' bright / You can see the city lights / cause I'm here to make it right.").
  • Back in Time: Having been talked out of suicide, the person reminisces on childhood, a time where nothing had gone wrong for them ("So take me back in time / To another world / When you can be mine / We don't have to worry / When you're by my side / There's nothin' I don't know / There's nothin' to decide / Apart from where we want to go").
  • Work it Out: The person has decided to go out and get help to overcome their issues with depression and suicidal thoughts ("Work it out, work it out / Think about it / Work it out, work it out / Talk about it / Work it out, work it out / Make it happen / Let's work it out, work it out / We've got to make it real." and "We all know / That life gets harder, / It's getting harder day by day / We can show / That we are trying / We're makin' sure that everyone can say: / You're the one / I can depend on / No one else can put it right / I'm someone / You can rely on / Cause we're not givin' up without a fight!").
  • Diamond in the Sky: The person has found a lover, it could be the person that talked them down from suicide or someone else, and has gotten help as they had wanted to do in Work it Out ("You're the one that makes me feel so high / Just like the diamonds in the sky / I never want to hear you say goodbye / Cause you're my diamond in the sky / You're the one that makes me feel so high / Just like the diamonds in the sky / I never want to hear you say goodbye / Cause you're my diamond in the sky.").
  • You're My Number One: A happy end, as the person has overcome their severe depression and suicidal thoughts, thanking their lover for giving them a true reason to keep on living life ("All I need is you / For always and forever / All you need is me / Remember when I say / All we need is love / For us to be together / 'Cause you're my number one!").

The songs, in order, tell a story
To explain:
  • "Can You Feel the Sunshine": The lyrics foretell of someone running away from something ("don't you feel that sometimes you just need to run away"), hoping to fight a brighter future.
  • "Living in the City": She's run away, and now lives in a new place, where she believes things will be better.
  • "Back in Time": She's starting to miss her old home and part of her wants to "go back in time" to be back where she started.
  • "Work it Out": Things aren't working out in her new home, and she's trying her best to come up with a solution.
  • "Diamond in the Sky": She realizes that what she had to begin with was best for her, so she longs to return.
  • "Super Sonic Racing": Going back home at the speed of sound.
  • "Number One": Her journey's over, and now she's happy.

The Tails Doll wasn't made by Eggman
It was made by Metal Sonic. Metal Sonic came to believe that Sonic kept winning because of help from his friends. So, in a moment of autonomy, it decided to make a "friend" for itself to even the odds. This would explain why it looks so shoddy, and why Eggman doesn't remember creating it.

The Tails Doll infiltrated the ranks of Eggman's army
Robotnik doesn't remember creating it for the simple reason that he didn't. It's a being with a different origin that infiltrated his forces' ranks. Perhaps it's some sort of cyber ghost sealed in its gem. Most likely, Robotnik came across it one day and assumed he made it after a particularly rough battle during an adrenaline rush and was too emotional at the time for it to register in his memory. He might think he intended it as a decoy or a spy, but only the doll knows why it exists or why it's in Eggman's army.

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