26. Tom T. Hall
Hall's songwriting has been compared to Chekhov's short stories and with good reason. "I couldn't write the 'Darling, you left alone and blue' or 'I'm drunk in this bar and crying' [songs] – I just didn't get it," he once said. "And so I started writing these story songs." Hall brought humor, warmth and some of the most vividly descriptive lyrics in the history of American music to songs like "Old Dogs, Children and Watermelon Wine," written after a brief encounter with a janitor at a bar at the 1972 Democratic Convention. "Don't Forget the Coffee Billie Joe" is about a seven-mile walk into town in the winter of '49 with a shopping list from dad that’s like a catalog of rural struggle and community ("mama needs her medicine / She's got that real bad cough / We'll get our check on Monday / Tell ol' Sam we’ll pay him off'). Hall's biggest hit was "Harper Valley PTA," a hilarious study in small-minded, small-town hypocrisy that was a Number One pop and country hit for Jeannie C. Reilly in 1968. An English major and committed liberal, Hall infused his songs with a learned tenderness, like in "The Hitchhiker," where he picks up a country boy in search of a job outside of Prestonsburg, Kentucky, buys him a diner hot dog ("with a lot of table ketchup") and arrives at the bottomless life lesson "boy, you’ll never make it without help." J.D.
Key Tracks: "That's How I Got to Memphis," "Old Dogs, Children and Watermelon Wine"