I want Booker to sing, only problem
Is it a good idea?

3025405 Why not, most great ideas don't seem like good ones when you think about it. I would suggest finding a song that would fit both him and the period.

It depends. We need a lot more information about it. Is he singing to someone? Is anyone else around? Can he sing well in your story? (We know from the game he can play guitar, but we don't hear him sing.) Describe the scene more for us, basically.

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Booker sits alone after a battle pony bodies littered around him hisself hatered boling to a point where he cant take it anymore, a dead pony still cluched a gitar in his hooves burnt to death by a Firey cluster. he turns it sits down and starts playing.

3028168 Not sure which song would go with that. If you ask in the Music Lover's group somebody might be able to help you.

3028168 I agree with Darkphantom, I have no idea what song he would play/sing that would be appropriate to the year 1912. Sorry I can't offer further help.