Failed attempts at living simple lives are what keep me coming back to you

[Wisemon]

using a soundboard that Weird Al used in some of his songs to fill void or something.

I like this idea. The little pauses need some effects right there.

Little hint before singing try and mix a cup of water with 3 tablespoons of honey, a tablespoon of lemon juice and gargle for the first swig.

I actually do drink green tea with honey, and I drink water between takes. I'll consider the lemon juice.

First voice: Do it like an Hip Hop monotone artist that is continually going through the lyrics as if it were spoken word.
Second voice: Same as the other except a wholestep up.
Third voice: Your singing voice, going over the first step
Forth voice: Your doppleganger of the third but adding variable twists.
Fifth voice: Just fillers.

Do you mean like overlapping the different voices all together, or just trying different voices? I think it would sound a bit too busy if I overlapped five voices at once.