"Angel Flying Too Close to the Ground" (1981)
Nelson played a version of himself in 1980's Honeysuckle Rose, a musical drama about a struggling country singer that was elevated above guilty pleasure status by its live-concert inspired soundtrack. Co-stars Amy Irving and Dyan Cannon, along with Emmylou Harris, Hank Cochran, Jeannie Seely and fiddler Johnny Gimble, joined Nelson and his Family band on the LP, which included songs like "Pick Up the Tempo" and "Heaven and Hell." The road anthem "On the Road Again" became the ubiquitous classic, but it's the artery-slicing "Angel Flying Too Close to the Ground" that deserves to be deemed an American standard. Later covered by both Bob Dylan and Alison Krauss, it's a bittersweet rumination on deep love and even deeper loss, with uncluttered production and one of Nelson's most vulnerable, compelling vocal performances of all time.