11 Legendary Artists Who Died Tragically in a Plane Crash Glenn Miller (1944) Born in 1904, Miller died in 1944 after his military plane fell from the sky. ... – 3. Buddy Holly and Ritchie Valens (1959) ... Patsy Cline (1963) ... Jim Reeves (1964) ... Otis Redding (1967) ... Jim Croce (1973) ... Lynyrd Skynyrd (1977) Jan 9, 2023