John Prine was an Army veteran walking a U.S. Postal Service beat in Chicago and writing songs on the side when Kris Kristofferson heard him and helped spread the word about Prine’s gifts. Pretty soon, he resigned as a letter carrier; his supervisor snickered, “You’ll be back.” Nearly 50 years later, this January, he was given a lifetime achievement Grammy for his contributions to songwriting. The singing mailman almost always had the last laugh.

Prine, who died on Tuesday from complications of the coronavirus, was legitimately unique. He took familiar blues themes — my baby left me — but filled them with whimsy and kindness. He liked a saucy lyric, and wrote movingly, in character, of the quiet lives and loneliness of humdrum people. He seemed like a Zen sage and offered an uncynical live-and-let-live morality in his songs, writing in a colloquial voice that revealed a love of the way Americans speak. He showed how much humor you could put in a song and still be taken seriously. He had less in common with any other songwriter than he did with Mark Twain.

He grew up in Maywood, a western suburb of Chicago, and was reared by working-class parents from Kentucky, where he often spent summers with relatives and fell in love with country music and bluegrass. By 13, he was performing in rural jamborees. When he debuted in 1971, in his mid-20s, he sounded like an old man already, so years later, when he got old and went through two cancer treatments, he still sounded like himself. From his first to his last, he wrote songs that were tender, hilarious, and wise, without grandstanding any of these traits. Here are 15 of the best.