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Singer Patsy Cline, who was killed in a crash of a Piper Comanche in 1963 (from the Autumn 2022 issue of Aviation History), was neither the first nor the last popular musician to die in an airplane crash. Here are some notable cases.

Glenn Miller (1944)

Buddy Holly, Ritchie Valens and the Big Bopper (1959)

Immortalized by Don McLean’s song “American Pie” as “The Day the Music Died,” the crash of a Beechcraft Bonanza on February 3, 1959, took the lives of 22-year-old Buddy Holly (“Peggy Sue”), Ritchie Valens (17) and J.P. Richardson (“The Big Bopper,” who was 28). Shortly after taking off from the airport in Clear Lake, Iowa, on a flight to Fargo, North Carolina for a show in nearby Moorhead, Minnesota, the single-engine airplane encountered bad weather and crashed in a cornfield. All aboard, including the 21-year-old pilot, Roger Peterson, died. Valens, whose big hit was “La Bamba,” got a seat on the airplane after winning a coin flip with guitarist Tommy Allsup. Waylon Jennings, then a member of Holly’s band, gave up his seat to Richardson, who was sick. The investigation blamed pilot Peterson, who was not prepared for the weather he encountered on the flight.

Buddy Holly, Ritchie Valens and the Big Bopper never made it to this concert (HistoryNet Archives).

Patsy Cline (1963)

Country singer Patsy Cline, 30, and three others died in a crash of a Piper Comanche on March 5, 1963. Cline was on her way back to her home in Nashville, Tennessee, after performing in Kansas City, Kansas. The pilot was her manager, Ramsey “Randy” Dorris Hughes. Bad weather had been making the trip difficult and forced several stops along the way. After taking off from Dyersburg, Tennessee, into rain, clouds and darkening skies, the airplane crashed to earth in the countryside about 75 miles west of Nashville. Cline, Hughes and musicians Harold Franklin “Hankshaw” Hawkins and Llody Estel “Cowboy” Copas were all killed. The accident investigators blamed pilot error.

Patsy Cline was returning home from this Kansas City show when her airplane crashed (HistoryNet Archives).

Jim Reeves (1964)

Country singer Jim Reeves, 40, died in a crash similar to Cline’s, except in this case Reeves was flying his own airplane. The singer, known for hits like “Four Walls,” took off from Batesville, Arkansas, on July 31, 1964, for a flight to Nashville. Reeves was at the controls of his single-engine Beechcraft 35-B33 Debonair. His only passenger was his manager, Dean Manuel. Reeves flew into a violent rainstorm over Brentwood, Tennessee, and apparently became disoriented. The airplane plunged into the ground at high speed. It took 42 hours to locate the wreckage in a search that included country stars Marty Robbins and Ernest Tubb.

Otis Redding (1967)

Soul singer Otis Redding, 26, died in the crash of his chartered twin-engine Beechcraft 18 on December 10, 1967. Redding and members of his band, the Bar-Kays, had taken off from the airport in Cleveland for a flight to Madison, Wisconsin, with pilot Richard Fraser. The weather was bad, with cold drizzle and fog. While on the approach to Madison the airplane plunged into Lake Monona. The exact cause of the crash remains undetermined, but the Beechcraft may have been experiencing engine problems. Of the seven passengers, the only survivor was 20-year-old Ben Cauley, one of the musicians. (The opening band for Redding in Madison that night was to be a local outfit called the Grim Reapers, featuring future Cheap Trick guitarist Rick Nielsen.) Four months after Redding’s death his single “(Sittin’ on) The Dock of the Bay” reached the top of the charts. It was his first #1 record.

Jim Croce (1973)

Singer/songwriter Jim Croce, 30, was a rising star on September 20, 1973, when he performed his last concert at Northwestern State University in Natchitoches, Louisiana. He had achieved chart success with “Bad, Bad Leroy Brown” and other songs and was working on a third album. Weary of the road, he was eager to get to the next and final stop on the tour in Sherman, Texas. The pilot of his chartered Beechcraft E18 was Robert N. Elliott, who had to make most of the three-mile trip to the airport on foot because he couldn’t get a cab. Immediately after takeoff from Natchitoches Regional Airport, the airplane hit a pecan tree. All six onboard, including guitarist Maury Muehleisen, comedian George Stevens, road manager Dennis Rast and Croce’s agent, Kenneth D. Cortese, died in the crash. The investigation blamed pilot error.

Lynyrd Skynyrd (1977)

Members of the country rock band Lynyrd Skynyrd (“Sweet Home Alabama,” “Free Bird”) were aboard a chartered flight of a twin-engine Convair CV-240 on October 20, 1977. The band’s fifth album, Street Survivors, had been released only three days before. The flight flew out of Greenville, South Carolina, en route to Baton Rouge, Louisiana, when it crashed near Gillsburg, Mississippi. The accident investigation determined that the airplane ran out of fuel because the pilots had neglected to properly check their fuel status. Lead singer Ronnie Van Zant (29), guitarist Steve Gaines (28) and backup singer Cassie Gaines (29) were killed, as was an assistant road manager and the pilot and copilot. Twenty other people aboard the Convair survived. MCA Records later re-released Street Survivors with a different cover—the original had shown the band surrounded by flames.

(Street Survivors was released three days before a plane crash killed three members of Lynyrd Skynyrd. The record label re-released the album with a different cover. )

Randy Rhoads (1982)

On March 19, 1982, Randy Rhoads, guitarist for rocker Ozzy Osbourne, died in the crash of a Beechcraft Bonanza in Leesburg, Florida. Rhoads, 25, was a passenger in the airplane, which was flown by Andrew Aycock, who drove a bus for the band. The airplane belonged to country singer Jerry Calhoun. The accident happened when Aycock, whose pilot’s license had expired, attempted to buzz Osbourne’s tour bus, clipped a wing on the bus, and crashed into Calhoun’s house. All three aboard the airplane, including the band’s seamstress, were killed. According to the report by the National Transportation Safety Board, “The pilot, who was a rock group driver, took an aircraft from the hangar without permission to joy ride members of the group.”

Ricky Nelson (1985)

Singer Ricky Nelson, 45, had become famous as one of the offspring of Ozzie and Harriet Nelson and played himself on his parents’ shows on radio and television. Interested in music, Nelson launched a musical career, with hits that included “Hello Mary Lou” and “Garden Party.” He was killed on December 31, 1985, when his airplane, a 1944 Douglas DC-3 that Nelson had purchased for use as a tour airplane, was attempting an emergency landing due to an interior fire. The DC-3 had taken off from Guntersville, Alabama, for a flight to Dallas and crashed outside De Kalb, Texas. The cause of the fire was believed to be a defective heater. The pilot and copilot survived but were badly burned; the other seven aboard were killed.

Stevie Ray Vaughan (1990)

After serving as David Bowie’s guitarist on the 1983 album Let’s Dance, Stevie Ray Vaughan, 35, enjoyed a successful solo career as a blues singer/guitarist with his band Double Trouble. He died early in the morning of August 27, 1990, in the crash of a Bell 206B JetRanger helicopter outside Elkhorn, Wisconsin. The helicopter had departed from the Alpine Valley Music Theater for a flight to Chicago’s Midway Airport following Vaughan’s concert appearance with Eric Clapton and others. Shortly after taking off, the helicopter crashed into a nearby ski mountain. All aboard, four passengers and pilot Jeff Brown, were killed. The cause was put down as pilot error; Brown might have experienced night blindness after taking off under bright lights and then ascending into fog and darkness.

John Denver (1997)

Singer-songwriter John Denver, whose hits included “Country Roads” and “Rocky Mountain High,” died on October 12, 1997, in the crash of a home-built aircraft he had recently purchased. Denver (born John Henry Deutschendorf Jr.) had been flying a Rutan Long-EZ on the Pacific Coast near Pacific Grove, California, when the airplane plunged into the ocean. Denver, 53, was an experienced pilot (although his license had been suspended following incidents of drunk driving) but investigators determined he had probably crashed after unsuccessfully attempting to switch fuel tanks in flight, a maneuver that may have led him to inadvertently hit the rudder pedal by mistake, leading to a loss of control. 

Aaliyah (2001)

Singer, dancer and actress Aailyah (full name Aaliyah Dana Haughton) was only 22 when she died in the crash of a twin-engine Cessna 402 on August 25, 2001. Aailyah had released three best-selling albums at the time of her death and was married briefly (and illegally) to her mentor, rapper and producer R. Kelly, at the age of 15. After shooting a music video, she and eight other people had boarded the chartered Cessna for a flight from the Bahamas to Florida. The airplane crashed just after takeoff, killing all aboard. Investigators found that pilot Luis Morales III had traces of drugs and alcohol in his system and was not rated to fly the Cessna, and that the airplane had been overloaded.