The most iconic images of John Prine were captured toward the end of his life. Photos from 21st century Grammy Awards ceremonies and concerts with friends find the late songwriter wrapped up in his craft, or flashing a charming smile as he soaks in the moment.

In later years, Prine surely understood how precious life could be. He'd warded off cancer twice and grew comfortable with gravely voice that truly suited his mature songwriting. Early album covers and black and white pictures find Prine at ease, with a thoughtful gaze protecting the songs that were surely coming together behind the scenes. Later on, he was much more prone to flash a grin.

Prine, who died on Tuesday (April 7) at the age of 73, transformed physically during his 50-year music-making career. At times in the mid-to-late 1970s, he was covered in hair — but as he pushed toward 40, he trimmed, shortened and styled.

Until his later years, Prine kept a fine mustache, but the 2018 cover of his The Tree of Forgiveness album finds him clean-shaven. There was always a certain wisdom about him that Kris Kristofferson picked up on straight away. Famously, the country music songwriting legend wrote in the liner notes of the John Prine album (1971) that Prine was 24, but wrote songs like he was 220 years old.

See Pictures of John Prine Through the Years:

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