The 50th captain never sees the ships in front of him hit the singularity! Indeed the captain never sees the singularity.
What happens is that their ship gets stretched by tidal forces, more and more, tending to inifinity, and then at some moment the captain 'hits the singularity'.
This is a way of saying they hit a region of spacetime where we don't know what happens. According to general relativity, spacetime just ends. But general relativity may become inaccurate under such extreme conditions.
(4/n)