On January 26, 2020, a Sikorsky S-76B helicopter, N72EX, being operated by Island Express Helicopters Inc. as a Title 14 Code of Federal Regulations (CFR) Part 135 on-demand flight, crashed into terrain in Calabasas, California. The pilot and the eight passengers died. One of the passengers was retired basketball player Kobe Bryant. Safety issues include the pilot's preflight weather and flight risk planning, the flight's entry into instrument meteorological conditions and the pilot's inadequate adverse weather avoidance, the pilot's spatial disorientation, influences on the pilot's decision to continue the flight into adverse weather, Island Express' incomplete implementation of its safety management system (SMS), the benefits of a mandatory SMS, the benefits of flight simulation devices for pilot training in adverse weather avoidance, the benefits of a flight data monitoring program, and the value of crash-resistant flight recorder systems in preventing future accidents. As a result of the investigation, the National Transportation Safety Board makes two new safety recommendations each to the Federal Aviation Administration and Island Express.