Experiments are reported in which the drag of single liquid droplets settling in a tall column of another lighter immiscible liquid are measured. The experimental data for the eight pairs of liquids that were tested covered a range of droplet Reynolds numbers from 10−3 to 104. Two regimes of droplet settling were encountered. In the first regime, the droplets remained spherical, and the drag agreed very well with established solid sphere drag models. In the second regime, the droplets became deformed and oscillated; the drag was found to depart suddenly from predictions of spherical models and to increase with increasing Reynolds number. Empirical models for the point of departure from spherical drag and the coefficient of drag in the unstable regime are derived.