So I've been thinking about bringing some music into the prison with my character. Jensen Ackles, the actor who plays Dean, has a great singing voice in my opinion and can play the guitar to boot (an example of which can be found
here and
here). While he's said in the past that Supernatural doesn't pay him to sing as Dean I believe he has proven that Dean can carry a tune when he wants to. Some evidence of which can be found below (except for one bit, but hell who doesn't love the eye of the tiger?).
So ultimately I picture Dean's singing voice being a bit between the two versions, and am taking some artistic license to say that back when he was a teen he was taught the basics of how to play a guitar (maybe from Bobby or another hunter).
I don't know if there are any guitars in the prison but I'm wondering if Dean happened to find one are there any other characters who are musically inclined and would want to jam out together?
Yes, I'm looking at you Jo. Don't think I didn't see that clip of you in Leverage here