Ritchie Valens, Buddy Holly and J.P. 'The Big Bopper' He was starting to make it big with his hit "La Bamba," but at only 17-years-old Ritchie Valens tragically died in a plane crash alongside music legends, Buddy Holly (r.) and J.P. "The Big Bopper" (l.), a few miles from Mason City Municipal Airport, near Clear Lake, Iowa on Feb. 3, 1959 -- also referred to as the day the music died. Glen Miller But they weren't the first plane-related deaths to hit pop music. Legendary bandleader Glenn Miller was the most popular artist in the 1940s. But he gave up a lucrative civilian lifetstyle to join the military in World War II. In 1944, we was set to fly from England to France to play for the troops who had recently liberated Paris. Miller's plane disappeared over the English Channel in 1944 and was never found. Otis Redding Otis Redding was on the cusp of stardom when he died in a 1967 plane crash. The soul singer's "Sitting on the Dock of the Bay," released posthumously, became a monster hit. Jim Croce Jim Croce died in a plane crash in 1973, just before his album "I Got a Name" was to be released. The small commercial plane crash was blamed on pilot error. Croce, aged 30, still gets significant radio airplay for hits like "Bad Bad Leroy Brown" and "You Don't Mess Around With Jim." Lynyrd Skynyrd By that time, another rock n' roll plane crash had cast its own looming shadow. On October 20, 1977, the plane carrying Lynyrd Skynyrd ran out of fuel and crashed in rural Mississippi, killing lead singer Ronnie Van Zant, guitarist Steve Gaines, and backup singer Cassie Gaines, along with the band's tour manager and the plane's pilot and co-pilot. Stevie Ray Vaughn Stevie Ray Vaughn died in a helicopter, which crashed into a ski slope after the legendary guitarist jammed with Eric Clapton in Wisconsin on August 26, 1990. He was just 35. Aaliyah R&B sensation Aaliyah died younger still. The Brooklyn native was just 22 when, after filming a music video, her plane went down shortly after takeoff on August 25, 2001. John Denver John Denver is one of several celebrities who died piloting his own plane, as an experimental two-seater he was piloting went down after takeoff on the coast of California on October 12, 1997. Patsy Cline Patsy Cline also died at the peak of her career, as severe weather brought her plane down in mountains near Camden, Tenn., on March 5, 1963.