The death of “Miss You” singer Oliver Tree on Sunday (June 14) in a helicopter crash in Rio de Janeiro, Brazil was the latest in a distressingly long list of aviation accidents involving helicopters and small aircraft that have taken the lives of beloved artists, their band mates and prominent concert promoters.

From the Feb. 3, 1959 weather-related crash of a small plane near Clear Lake, Iowa that killed early rock icons Buddy Holly, Ritchie Valens and J.P. “The Big Bopper” Richardson — commonly referred to as “the day the music died,” in honor of Don McLean’s 1971 song “American Pie” — to the deaths of six people, including 32-year-old Tree (born Oliver Tree Nickell) over the past weekend, deadly aviation accidents can sometimes feel like a dark cloud looming over the music industry.

The list of tragic airborne deaths over the past half-century or so reads like a grim, flashing signpost about the potential dangers of eschewing commercial flights or road travel in favor of taking off in smaller craft. A list of just some of the lives lost in such accidents includes:

The tally also includes soul icon Otis Redding, early rocker Ricky Nelson, Lynyrd Skynyrd guitarist Ronnie Van Zant (and guitarist Steve Gaines), country singer Troy Gentry of Montgomery Gentry, concert promoter Bill Graham, Colombian singer Yeison Jiménez and, in 1991, eight members of country icon Reba McEntire’s band when the wing of the twin-engine executive jet they were traveling in hit a rock on the side of Otay Mountain near San Diego.

So why do artists take the seeming risk of flying on smaller planes and helicopters? Often times, if they can afford it, it allows them to avoid hassles of delayed, crowded commercial flights where they risk arriving late to gigs, having their equipment lost, stolen or damaged, getting sick when crowded in with hundreds of other passengers or being descended upon by adoring fans or paparazzi. Such flights can also take some of the time pressure off flying between gigs, allowing them to take off on their own schedule and pull off tight turnaround times.

Such jet-setting is not cheap, though, with trips on private jets ranging between $15,000 to $250,000 per flight or more, and some planes clocking in at $50,000 an hour. The risks are also significantly higher, with the aviation/accident injury law firm rESQ reporting that private jets (specifically the business type often used by musicians) experience roughly 0.1-0.3 fatal accidents per 100,000 flight hours, versus approximately 0.006 for scheduled commercial flights and 0.9-1.1 for general aviation overall, according to National Transportation Safety Board data. (The report also noted that crashes involving “true business jets” such as Gulfstreams or Citations, are “rare events,” with most fatal general aviation accidents involving small, single-engine piston aircraft, not turbine-powered private jets.)

So, why do the stars still do it?

“There’s obviously a high invincibility factor here, kind of like, ‘Why do artists do drugs?’,” says Rob DelliBovi, founder and CEO of RDB Hospitality, which coordinates travel and accommodations for musicians and other clients who can afford the high cost of bypassing commercial travel. “They have made it through the ranks and they don’t think anything can happen to them.”

But, he adds, since the tragic 2020 helicopter crash involving Los Angeles Lakers star Kobe Bryant that killed the basketball legend, his 13-year-old daughter and seven others, his clients have definitely shown a heightened awareness and focus on safety. “People are more concerned now with, ‘Is this good equipment? What is the [plane’s] tail number? Are there two pilots? Does the plane have an unblemished safety record?,'” he cited as among the questions he frequently gets now, sometimes directly from the artist.

Michael Henderson, owner of Legal Eagles Aviation, which specializes in accident reconstruction and aviation safety — with founder Henderson often acting as expert witnesses in aviation-related court cases — says another reason clients might opt for private is a lack of reliable routes between destinations, or, most crucially, the need for speed. He too notes, however, that that desire does not trump a need to feel secure in a smaller aircraft.

Henderson rejects the notion that private air travel is much more dangerous than commercial, noting that the typically ex-military or ex-commercial pilots who fly “135” aircraft — the FAA designation for commercial, non-scheduled, on-demand air carriers such as private jet charters or air taxis — are often just as, or more qualified than some commercial pilots when it comes to hours in the air and safety training. “These are not rookies. They’re highly experienced.”

In addition, the physicist and part-time musician says the kind of 135 planes they fly often have a highly concentrated maintenance group because they cannot afford significant downtime, given their on-demand nature. They are also at the service of artists who can afford to pay for bespoke service and, who are, frankly, typically in the air way more than the average flier.

“It’s a math thing — the more your roll the dice the more likely you’ll get snake eyes and the higher the probability of failure, which is not different for musicians than anyone else,” says Henderson. He also points out that even though the chances of being injured or dying on a private flight versus commercial flights is the same for musicians, we are more likely to hear about it because of their notoriety.

Plus, in some regions, such as Latin America, artists’ routing might require private flight because commercial carriers do not have regular, timely service to the cities and regions where events take place. In Mexico, artists, such as late singer Rivera, must travel by private plane because they book small town fairs and private parties in places where there is no commercial air service. That’s especially true if they have multiple gigs in one night, which is not uncommon, making her death especially poignant, because, like Jiménez and Brazilian star Marília Mendonça, 26 — who died in a plane crash in 2021 — they are genuinely working artists commuting to work.

As another example, DelliBovi cited the Lollapalooza festivals in Chile, Argentina and Brazil that often take place either on the same weekend, or within a week of each other in March. “It is the only option if you’re playing Sao Paolo on Friday and Buenos Aires on Saturday — there is no other way that doesn’t involve a connection or a layover that might make it so you can’t get to the second show,” he says, adding that the busy European summer festival circuit also has some bands playing multiple gigs over several weeks with potentially set-busting travel times on commercial carriers.

He also pointed to the super high-end Aman resort in the Dominican Republic, a favorite of his clients, which he says is nearly three hours from an airport. “You don’t want to spend six hours flying when you can go private into a local airstrip,” he says.

While it was still unclear at press time what caused the crash that killed singer Tree, Henderson says when it comes to taking off, pilots and their crews have the final say. That’s even if celebrities (and their packed schedules) sometimes try to push them to fly routes that commercial planes can’t, because they have less flexibility to fly around storms or divert to smaller airports that are not available to major carriers.

“It’s up to the pilot to say, ‘Conditions suck, I’m not flying,'” he says of situations such as those preceding the Vaughn crash — which the NTSB determined was caused by foggy conditions and the pilot’s lack of certification to fly in poor visibility — referring to the aviation designation of the person legally responsible for safe flight, “PIC,” which stands for “pilot in command.”

DelliBovi says since the Bryant accident, artists are more aware — and sometimes, wary — of flying on helicopters. But, given the option of getting from JFK airport in New York to Manhattan in 11 minutes on a chopper versus fighting traffic for two hours, “people are willing to do it… and making sure they send that extra sentence [in the contract] about vetting and qualifications. The biggest, smartest names are all flying on them, and the amount of people scared to fly is low. It’s worth it to them — 90% of artists would [fly private] it if they could afford it — and they understand the risk.”

In a 2025 Billboard story on the world of high-end private jets, Elevation Aviation Group CEO Greg Raiff said that while helicopters offer the most flexibility, “75 or maybe 80% of our customers refuse to get on one these days,” in the wake of the Bryant crash.

The New York Times reported that same year that, according M.I.T. Sloan School of Management statistics professor Arnold Barrett, the risk of dying on a [commercial] flight is “close to zero,” with the last five years among the “safest in the history of commercial aviation.” By comparison, the odds of dying in a car crash are about 1 in 95. The paper also noted that the average fatal accident rate for all U.S. helicopters from 2019-2023 was 0.690 per 100,000 flight hours, which was significantly higher than that for commercial and charter planes. In addition, helicopters had an accident rate of 3.92 per 100,000 hours, versus 1.04 for charter services and 0.15 for commercial airlines.

The price tag is often eye-popping for these flights, but DelliBovi suggests that just like you would not want to opt for a more affordable doctor when getting major surgery, he counsels his clients that “cheaper is not better.” If a plane’s owner offers a $10,000 discount over another qualified carrier, “I would tell them not to book that plane. We’re flying around the biggest names in the world and we can’t afford to mess around with ‘Johnny’s Plane Company.'”

When it comes down to it, Henderson says there is “enormous” pressure on private pilots to get their famous clients where they are going as fast and efficiently as possible. And while tragic celebrity flying-related deaths make headlines and make it seem like they are frequent occurrences, “It’s actually less dangerous if you do the math,” he says about the probability of a musician dying or being severely injured in a private aviation accident over that of a civilian or CEO perishing in that same manner.

“How many musicians are flying every day and how many crashes are there? It’s generally no different than anyone else flying in a 135, from a bricklayer to a rodeo star.”