The death of “Miss You” singer Oliver Tree in a helicopter crash in Rio de Janeiro, Brazil, on Sunday (June 14) became the latest in a tragically long list of aviation accidents involving helicopters and small planes that have claimed the lives of beloved artists, their bandmates and prominent concert promoters.
On February 3, 1959, early rock icons Buddy Holly, Ritchie Valens, and JP “Big Bopper” Richardson were killed in a weather-induced small plane crash near Clear Lake, Iowa. The incident (commonly referred to as “The Day Music Died” after Don McLean’s 1971 song “American Pie”) has left six people dead, including 32-year-old Tree (real name Oliver Tree Nickell). By the end of the week, it can feel like a deadly air crash is casting a dark cloud over the music industry.
The list of tragic aviation fatalities over the past half-century or so seems like a grim, flashing signpost about the potential dangers of taking off in small aircraft in favor of commercial flights and land travel. A small list of lives lost in such accidents include:
Patsy Cline — A Piper PA-24 Comanche small plane crashed in bad weather on March 5, 1963, killing 30-year-old Cline and fellow country artists Cowboy Copas and Hawkshaw Hawkins. Jim Croce — A Beechcraft E18S twin-engine light airplane crashed shortly after takeoff due to fog on September 20, 1973, killing 30-year-old Croce and five others. Randy Rhoads, the 25-year-old guitarist for the beloved Ozzy Osbourne, died on March 19, 1982, when a single-engine four-seater plane being flown (without permission) by bus driver and private pilot Andrew Aycock attempted to whirl past Osbourne’s tour bus, but the wing became wedged in the top of the vehicle, sending the plane into a fatal tailspin. Stevie Ray Vaughan – A 35-year-old blues guitarist and singer and four others were killed on August 27, 1990, after a performance at the Alpine Valley Music Theater in Alpine Valley, Wisconsin, when the twin-engine Bell helicopter they were riding in took off due to poor visibility and crashed into a nearby ski slope. John Denver — Denver, 53, an experienced pilot, died on October 12, 1997, when his lightweight, homemade Rutan Long EZ two-seater crashed into Monterey Bay after the fuel selector handle was difficult to reach. Aaliyah – On August 25, 2001, a twin-engine Cessna 402 light plane crashed and burst into flames after taking off from the Abaco Islands in the Bahamas, killing the 22-year-old singer and eight others. Investigators found the plane was overloaded with baggage and the pilot was not certified to fly that type of aircraft. Jenni Rivera — Mexican singer and actress, 36, died on December 9, 2012, when the 10-passenger Learjet she and six others were aboard crashed near Iturbide, Mexico, in what investigators believe was an unspecified loss of control.
This tally includes soul icon Otis Redding, early rocker Ricky Nelson, Lynyrd Skynyrd guitarist Ronnie Van Zant (and guitarist Steve Gaines), and country singer Troy Gentry (Montgomery Gentry). Also included are concert promoter Bill Graham, Colombian singer Eison Jimenez, and eight members of country icon Reba McEntire’s band, whose twin-engine executive jet she was flying in 1991 hit a rock with its wings. Side view of Mount Otay near San Diego.
So why do artists take the seemingly risk of flying in small planes or helicopters? In many cases, if you have the money, you can avoid the hassles of flight delays and crowds. If you do, you risk arriving late to the show, losing, having your equipment stolen or damaged, getting sick from being crowded with hundreds of other passengers, and being attacked by adoring fans and paparazzi. Such flights also take some of the pressure off of travel time between gigs, allowing you to take off on your own schedule and safely depart in a short turnaround time.
But these jet setups don’t come cheap, with private jet travel costing anywhere from $15,000 to more than $250,000 per flight, and depending on the flight, $50,000 per hour. The risks are also significantly higher: According to a report by aviation accident and injury law firm rESQ, data from the National Transportation Safety Board shows that private jets (the business type, especially the type often used by musicians) have about 0.1 to 0.3 fatal accidents per 100,000 flight hours, compared to about 0.006 on scheduled commercial flights and 0.9 to 1.1 for general aviation overall. (The report also noted that crashes involving “true business jets” such as Gulfstreams and Citations are “rare events” and that most general aviation fatalities involve small, single-engine piston aircraft rather than turbine-powered private jets.)
So why do stars still do it?
“Obviously there’s a very high element of invincibility here, like, ‘Why would an artist turn to drugs?'” says Rob Delivovi, founder and CEO of RDB Hospitality. RDB Hospitality coordinates travel and accommodations for musicians and other clients who can afford the high costs of avoiding commercial travel. “They have come up through the ranks so they don’t expect anything to happen to them.”
But he added that his clients have definitely shown an increased awareness and emphasis on safety since the tragic 2020 helicopter crash involving Los Angeles Lakers star Kobe Bryant, which killed the basketball legend, his 13-year-old daughter, and seven other people. “People are now asking, ‘Is this a good device? [plane’s] Tail number? Are there two pilots? Does this plane have an impeccable safety record? ” he mentions as one of the questions he receives frequently these days, sometimes even directly from artists.
Michael Henderson, owner of Legal Eagles Aviation, which specializes in accident reconstruction and aviation safety (and who often acts as an expert witness in aviation courts), says another reason customers choose private aviation is the lack of reliable routes between destinations or, most importantly, the need for speed. But he also points out that that desire does not outweigh the need for peace of mind in a small aircraft.
Henderson rejected the idea that commercial air travel is much more dangerous than civil aviation, pointing out that the typical military or former civilian pilots who fly “135” aircraft (an FAA designation that refers to commercial, non-scheduled, on-demand airlines such as private jet charters and air taxis) are often as qualified or better qualified than some commercial pilots when it comes to long flights and safety training. “They’re not new. They’re very experienced.”
Additionally, the physicist and part-time musician said the 135 planes they fly often have very focused maintenance groups because they cannot afford significant downtime given their on-demand nature. They also have the services of artists who can afford to pay for bespoke services and, frankly, generally fly far more than the average airline.
“It’s a mathematical thing. The more you roll the dice, the more you roll, the more likely you are to fail. It’s no different for musicians than it is for anyone else,” Henderson says. He also points out that musicians are just as likely to be injured or killed on a private plane as they are on a private plane, but because of their notoriety, they’re more likely to hear about it.
Additionally, in some regions, such as Latin America, commercial airlines do not provide regular and timely service to the city or region where the event will be held, so traveling the artist may require a dedicated flight. In Mexico, artists like the late singer Rivera have to travel by private plane to book small town fairs and private parties in places without commercial flights. Like Jimenez and Marilia Mendonça, the 26-year-old Brazilian star who died in a plane crash in 2021, they’re also true working artists who commute to work, so that’s not unusual, especially when they perform multiple gigs a night.
As another example, DelliBovi cited the Lollapalooza festivals in Chile, Argentina and Brazil. These festivals are often held on the same weekend or within a week in March. “If you’re playing São Paulo on Friday and Buenos Aires on Saturday, that’s your only option, because you might have a layover or layover and not be able to get to the second show,” he says, adding that the crowded European summer festival circuit can significantly reduce travel time on commercial airlines, and some bands play multiple gigs over several weeks.
He also mentioned a customer favorite, the ultra-luxury Aman resort in the Dominican Republic, which is nearly three hours from the airport. “You don’t want to spend six hours on a plane when you can go to your local airstrip privately,” he says.
The cause of the crash that killed singer Tree was not yet clear at press time, but Henderson said the pilot and his crew had the final say on takeoff. Even though celebrities (and their tight schedules) sometimes try to force celebrities (and their tight schedules) to fly routes that commercial airlines cannot fly because they have less flexibility to fly in storms or divert to smaller airports that are unavailable to major airlines.
“It’s up to the pilot to say, ‘Things are bad, I’m not going to fly.'” For conditions like the one before the Vaughn crash, the NTSB determined that the pilot’s lack of qualifications to fly in foggy conditions and low visibility were the culprits, he said, referring to the aviation designation “PIC” (short for “pilot in command”) for the legal officer responsible for safe flight.
Delivovy said that since Bryant’s accident, artists have become more aware and sometimes cautious about flying in helicopters. But given the option of taking an 11-minute helicopter ride from New York’s JFK Airport to Manhattan versus the option of fighting traffic for two hours, “people are willing to do that…and we’re making sure to send in additional sentences.” [in the contract] Regarding screening and qualifications. The greatest and brightest celebrities all fly, and there are only a few people who are afraid to fly. It’s worth it to them — 90% of artists would. [fly private] If you can afford it, that’s fine, and you understand the risks. ”
In a 2025 Billboard article about the world of luxury private jets, Elevation Aviation Group CEO Greg Reiff said that while helicopters offer the most flexibility, “75, maybe 80 percent of our customers are refusing to fly in helicopters these days” in the wake of Bryant’s crash.
That same year, the New York Times reported that according to Arnold Barrett, a professor of statistics at MIT’s Sloan School of Management, the risk of dying in an accident is high. [commercial] Flight status has been “close to zero” and the past five years have been “the safest in the history of civil aviation.” By comparison, the chance of dying in a car accident is about 1 in 95. The paper also noted that the average fatal accident rate for all U.S. helicopters from 2019 to 2023 was 0.690 people per 100,000 flight hours, which was significantly higher than for commercial and charter aircraft. Additionally, the accident rate for helicopters was 3.92 per 100,000 hours, compared to 1.04 for charter flights and 0.15 for commercial airlines.
While the prices of these flights are often eye-popping, Delivovi advises clients that “cheaper doesn’t necessarily mean better,” just as you wouldn’t want to choose a more affordable doctor for a major surgery. If a plane owner offers you a $10,000 discount over other eligible airlines, say, “I would tell them not to book that plane. We fly the biggest names in the world, and we can’t afford to mess with ‘Johnny’s Airplane Company.'”
After all, Henderson says commercial pilots are under “huge” pressure to get high-profile clients to their destinations as quickly and efficiently as possible. And while tragic airplane-related deaths of celebrities make headlines and make it seem like they happen all the time, “if you do the math, it’s actually not that dangerous,” he says, adding that musicians are more likely to be killed or seriously injured in a civil aviation accident than civilians or CEOs alike.
“How many musicians fly on planes every day, and how many accidents do they cause? It’s usually no different than anyone else flying a 135, from bricklayers to rodeo stars.”
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