It almost has the certainty of scientific law: Any hell-raising musician will reach his commercial peak with a song that’s slow and sentimental. It certainly proved to be the case for Ronald Clyde Crosby, better known as Jerry Jeff Walker. Like Townes Van Zandt, another Texas outlaw-country legend, he managed to become famous despite never having a hit record of his own. He came closest with this song, recorded in Memphis in June 1968. It reached No. 77.
He recorded it again a month later for the LP of the same name, this time in New York with different musicians, including David Bromberg, who backed Walker on tour for a couple of years.
The song didn’t become a standard until the Nitty Gritty Dirt Band recorded it for their album “Uncle Charlie and His Dog Teddy” in 1970. It was released as a single and caught fire, reaching No. 9 on the Hot 100 in early 1971, highly unusual for a release by an old-timey folk/country band. The song was preceded, both on the LP and the original, by an interview with the eponymous Uncle Charlie and contributions from his dog Teddy, which might be why the line “after 20 years he still grieves” hits like a harpoon. This pooch has drawn more tears than any dog since Ol’ Yeller.
That version opened the floodgates. It been recorded by well over 100 artists, including Nina Simone and Bob Dylan. Sammy Davis Jr. made it a signature song, performing it as a concert tearjerker for more than 20 years.
The song has been translated into German and Finnish. You’ll notice that you don’t need to understand the lyrics for the it to sound sad and sentimental, which also explains the dozens of instrumental covers.
Everyone knows Walker wrote the tune after meeting a street dancer in a jail in New Orleans, and that the person wasn’t the real Bill “Bojangles” Robinson. But most people don’t realize that the guy in the drunk tank with Jerry Jeff was actually white — the New Orleans jails were still segregated in 1965, when Walker was briefly incarcerated. Wilmington’s own David Bromberg has been explicating it for audiences for nearly 50 years, varying the stories in his spoken interlude over the years. This version was included on his “Demon in Disguise” album from 1972. In more recent live performances, he notes that Walker used “minstrel shows” because it fit the meter better than “medicine shows,” and that he left out the fact that the title character was a three-time widower — but became an alcoholic only after the dog died.
Walker’s fame wasn’t based only on this song — once he made Austin his home in the early ’70s he became one of the founding fathers of the outlaw country movement and Austin’s now world-renowned music scene. But odds are his addition to the American songbook will be his longest-lasting legacy.