On October 4, 1975, country music legend Willie Nelson achieved his first No. 1 hit on the Billboard Hot Country Singles chart with “Blue Eyes Crying in the Rain,” a milestone that came at age 42 after years of struggling as a songwriter and performer, marking the dawn of his superstar status and the outlaw country movement. The sparse, haunting rendition from his concept album Red Headed Stranger not only topped the country charts but crossed over to No. 21 on the Billboard Hot 100, earning Nelson his first Grammy for Best Country Vocal Performance, Male, at the 18th Annual Grammy Awards. Written in 1945 by Fred Rose and previously recorded by artists like Roy Acuff, Hank Williams, and Conway Twitty, the song’s simple arrangement—featuring just Nelson’s voice, guitar, and a touch of steel—captured the raw emotion of lost love, proving that persistence and authenticity could triumph over Nashville’s polished sound.

Born April 29, 1933, in Abbott, Texas, Nelson grew up in poverty, raised by his grandparents after his parents separated. Learning guitar from his grandfather, he performed locally by age 10, influenced by honky-tonk, western swing, and polka. A brief Air Force stint and early marriage to Martha Mathews in 1952 led to DJ work in Texas and Washington, where he self-released demos. By the late 1950s, Nelson moved to Nashville, penning hits like “Crazy” for Patsy Cline (1961) and “Hello Walls” for Faron Young, but his own recordings under RCA producer Chet Atkins stalled, frustrating him with the label’s control over material and style.

The 1960s saw modest success—two Top 10 singles in 1962 (“Touch Me” and “Willingly” with Shirley Collie)—but no breakthroughs, leading Nelson to sell songs for survival. A 1969 house fire in Tennessee prompted his return to Texas, where he embraced long hair, beards, and the “outlaw” vibe, rejecting Nashville’s conservatism. Signing with Atlantic in 1973, albums like Shotgun Willie and Phases and Stages hinted at change, but Red Headed Stranger (1975) on Columbia—recorded in three days for $20,000—exploded, despite label doubts over its “tinny” sound. The album’s narrative of a preacher’s guilt and flight resonated, with “Blue Eyes” as its emotional core.