Rise to Fame
Nashville didn't know what to do with him. He spent the early 1960s writing songs that other people got famous for ("Crazy" for Patsy Cline, "Hello Walls" for Faron Young) while barely cracking the charts as a performer. He quit Nashville, moved back to Texas in the early 1970s, grew his hair long, and started playing for crowds that mixed country fans with hippies. Red Headed Stranger (1975), a concept album Columbia Records thought was too sparse to release, went to number one anyway. "Blue Eyes Crying in the Rain" became his first chart-topper, and the outlaw country label finally gave the industry a box to put him in.
In the Spotlight
The IRS seized his assets in six states in November 1990, a $32 million bill eventually settled for $9 million. His response was to cut The IRS Tapes (1992) in a revenue-sharing deal with the government that generated $3.6 million toward the debt. He reached a settlement with the IRS in February 1993. At 92, he's releasing Dream Chaser (May 2026), his 79th solo studio album, with a new co-write with Bob Dylan on the tracklist. The Rock and Roll Hall of Fame finally inducted him in 2023, forty-eight years after Red Headed Stranger went to number one.
Side Notes
The guitar named Trigger (a 1969 Martin N-20) has a hole worn clear through the body from decades of playing. When his house burned down, he ran back inside to save it and a couple pounds of weed. He wrote "On the Road Again" on an airplane barf bag, mid-flight, at a director's request. He holds a second-degree black belt in GongKwon Yusul. Before Nashville, he worked as a tree trimmer, door-to-door salesman, and bar bouncer. His breakthrough songs got him very little: "Family Bible" sold for $50. The songs made other people famous first.