This might be a dumb question, but should my voice strain and/or stop working when i tilt my head back? it gets faint and raspy when i tilt up around 75% and if i tilt back fully, no voice at all just an airy sound.

Mechanical block: Tilting your head back can result in a mechanical blockage of your windpipe and stretching of your vocal cords causing them to not allow air to pass through. This is not a life threatening problem as a simple head position correction can reopen your windpipe. Try not tilting your head so far back if you need to sing while looking up.