Used to describe a situation that is getting progressively worse, not just a one-time event. His grades went from bad to worse last semester.
Pro Tip 2/3
Not Literal
Sometimes used figuratively to emphasize a decline in quality, not necessarily from bad to the worst possible. After the lead actor left, the show went from bad to worse.
Pro Tip 3/3
Emphasizing Trouble
Can be used to stress how troubling or difficult a situation is becoming. When they lost their map, their trip went from bad to worse.