On January 26, 2020, a Sikorsky S-76B helicopter crashed into a hillside in the city of Calabasas, California, around 30 mi (48 km) northwest of downtown Los Angeles, while en route from John Wayne Airport to Camarillo Airport. All nine people on board were killed: retired professional basketball player Kobe Bryant and his 13-year-old daughter Gianna; baseball coach John Altobelli, his wife Keri, and their 14-year-old daughter Alyssa; Sarah Chester and her 13-year-old daughter Payton; basketball coach Christina Mauser; and the pilot, Ara Zobayan.

The accident was then investigated by the National Transportation Safety Board (NTSB) which concluded that it was caused by continued VFR into IMC: the helicopter entered low cloud cover, which caused the pilot to lose his sense of orientation, and thus lose control of the helicopter.

On Sunday, January 26, 2020, at approximately 9:06 a.m PST (17:06 UTC), eight passengers and one pilot departed from John Wayne Airport (SNA) in Orange County, California, in a 1991 Sikorsky S-76B helicopter, registration N72EX. They were heading to a basketball game at Bryant's Mamba Sports Academy in Newbury Park, where he was scheduled to coach his daughter's team. Flight history records showed that the helicopter had flown the same journey the day before without incident to Camarillo Airport (CMA), a major general aviation airport about 20 minutes by car from Mamba Sports Academy. The previous day's flight had taken only 30 minutes; in contrast, driving from Bryant's home in Newport Beach to the academy would have taken at least 2 hours.

A number of video recordings of the crash area were available, and although none showed the crash itself, the sound of the helicopter and the crash was recorded. In particular, surveillance cameras installed at the Agoura Pony Baseball Fields provided overlapping coverage of the final parts of the flight path. The FAA conducted a visibility study which used frequency analysis to determine when the aircraft made the closest approach to each camera, ground-speed, engine RPM, and likely inflight visibility by comparing video recorded during the accident period to clear-sky imagery. The report concluded that, at the moment of the accident, the estimated visibility ranges were between 1–1.5 miles (1.6–2.4 km).

The Los Angeles Police Air Support Division had grounded its police helicopters on the morning of January 26 due to poor visibility and low ceiling; Air Support Division rules require at least 2 miles (3.2 km) of visibility and an 800-foot (240 m) cloud ceiling. At the time that N72EX took off from SNA, visibility was 5 miles (8.0 km) with a ceiling of 1,300 feet (400 m). It was operated by Island Express Helicopters Inc. as a 14 CFR 135 (Part 135) on-demand passenger flight under visual flight rules (VFR). Flying through clouds is possible if a pilot elects to operate under instrument flight rules (IFR), but the company's Part 135 operating certificate, issued in 1998, limited operations to on-demand VFR-only flights. Even if the company's operating certificate and its own internal policies had allowed for flying under IFR, that option could still have led to lengthy delays and detours (thereby using up any anticipated time savings) because of severe congestion in Los Angeles controlled airspace. Bryant's celebrity status would not have given the helicopter priority in that airspace.

According to an automated weather station, the ceiling (distance from ground to bottom of the cloud layer) at the Van Nuys Airport was 1,100 feet (340 m) above ground level. Closer to the site of the crash, the cloud top extended up to 2,400 feet (730 m) above mean sea level.

Because visual flight rules prohibit a pilot from flying into or near clouds, the helicopter remained at an altitude of 700 or 800 feet (210 or 240 m) above mean sea level (AMSL) while flying northwest from SNA. On most of its previous flights to Camarillo, the helicopter had turned west at downtown Los Angeles and flown over the Santa Monica Mountains until it picked up the Ventura Freeway (US 101). On January 26, that was not an option for VFR flights because of a deep marine layer which had pushed fog from the Pacific Ocean into the Santa Monica Mountains. Instead, the helicopter continued northwest, passed over Boyle Heights near Dodger Stadium, and began following the route of the Golden State Freeway (I-5); as the flight approached Glendale, pilot Zobayan requested permission from the Hollywood Burbank Airport air traffic controllers to transition to following the Ventura Freeway (US 101). Burbank controllers advised him that weather conditions around the airport dictated IFR and held the helicopter circling in a holding pattern for 11 minutes starting at 9:21 a.m. PST (UTC−08:00) before granting it permission to proceed into the controlled airspace around Burbank Airport. The hold allowed two inbound flights to land; while holding, Burbank informed Zobayan the cloud top extended to an altitude of 2,400 ft (730 m). Burbank called Van Nuys, which was also operating under IFR, and Van Nuys advised Burbank to take Zobayan north of Van Nuys.

Permission to proceed was granted at 9:32 a.m. (17:32 UTC) under special VFR, requiring the pilot to stay under 2,500 feet (760 m) altitude. The helicopter climbed to an altitude of 1,400 feet (430 m) AMSL, which Zobayan confirmed with Van Nuys at 9:35 a.m. (17:35 UTC). After proceeding through the Burbank controlled airspace, the flight turned west, following the Ronald Reagan Freeway (SR 118) as it passed into the Van Nuys Airport controlled airspace; the Van Nuys controllers shortly afterward approved a turn southwest towards the Ventura Freeway (US 101) at 9:39 a.m. (17:39 UTC). Zobayan then confirmed he was still in VFR flight conditions at 1,500 feet (460 m) and acknowledged the handoff to Southern California air traffic control (SCT).