Another interesting result (which I bring up just because this thread needs more discussion ) is that if they were to reach the bottom at the same speed (say the heavy guy had been breaking) and then coast on a level surface, the lighter guy will slow down faster.

In fact, I believe that even if they were to reach the bottom at the same speed and then coast up a hill, the heavy guy would go further because they would both suffer the same deceleration from gravity, but since the force of air resistance would be the same on both, the heavier guy would receive less deceleration from air resistance (a = F/m).

So if it's a short hill, the heavy guy might not get dropped after all.