Ride around the hills and mountains of CO, and you will see examples every day;
On the climbs, it is the little people who leave the big people (like myself) behind.
Then on the descents, the little people get left behind.

As for dropping two objects of different weights;
Ask any skydiver if a heavy person and a light person fall at the same rate.
As someone else pointed out, that is true only in a vacuum.
Small skydivers on freefall teams routinely wear lead weights to bring their fall rates up to the same as their bigger teammates.