Experiments were conducted on the interactions of two different-sized deformable drops moving due to gravity in an immiscible viscous fluid at low Reynolds number. As the drops come close to each other, several interactions are possible: (i) separation of the drops, (ii) capture of the smaller drop behind the larger drop, (iii) breakup of the smaller drop into two or more drops, and (iv) pass-through of one drop through the other, with possible cycle interaction or leap-frogging. The interactions depend on several system parameters, including the drop-to-medium viscosity ratio, the radius ratio of the two drops, the initial horizontal offset of the two drops at large vertical separation, and the gravitational Bond number (which represents the ratio of buoyant forces to interfacial tension forces for the larger drop and describes how much the drops will deform). Experimental analysis was conducted by videotaping trajectories of glycerol–water drops of various compositions falling in castor oil. The results show good agreement with available theoretical results, both for interaction maps and individual trajectories. The results also provide data beyond the present limitations of theoretical algorithms and reveal the new pass-through phenomenon.