This greatly depends on the objects that are dropped, the height the experiment is performed from and wether or not it is conducted in a vacuum. In a vacuum a feather and a bowling ball will hit at the same time whereas outside of a vacuum the results are completely different.
As an objects mass increases it has a tendency to overcome air resistance and obtain maximum velocity quicker. At least that’s how I understand it. Please correct me if I’m wrong.
Well its obviously a bit more complicated than that e.g. the shape of the object can have a huge effect on it's falling velocity in air.
Just think of the difference between a closed and an open parachute both of which have exactly the same mass.