James Butler “Wild Bill” Hickok fired a steadied shot from 75 yards at Davis Tutt with a .36-caliber Colt 1851 Navy Revolver on July 21, 1865, in Springfield, Missouri. According to the history of the event, Davis Tutt fired first, and Wild Bill braced his pistol across his support forearm and hit Tutt right in the heart. While the events leading up to this duel were largely attributed to terrible decision-making, the fact that his shot hit his mark is pretty incredible considering the technology of the time.