An experiment is reported in which an object which can rest in multiple stable configurations is dropped with randomized initial conditions from a height onto a flat surface. The effect of varying the object's shape on the probability of landing in the less stable configuration is measured. A dynamical model of the experiment is introduced and solved by numerical simulations. Results of the experiments and simulations are in good agreement, confirming that the model incorporates the essential features of the dynamics of the tossing experiment. Extrapolations based on the model suggest that the probability of an American nickel landing on edge is approximately 1 in 6000 tosses.