AUK’s Chain Gang: The Highwaymen “Desperados Waiting for a Train”

Last week’s chainganger, Guy Clark, was often referred to as the ‘Fifth Highwayman’, in relation to his connections with the famous supergroup, so it is probably no coincidence that the second single release from The Highwaymen’s 1985 debut album ‘Highwayman’ was ‘Desperados Waiting For A Train’, penned by Clark back in 1973. The song is about a man who was like a grandfather to him, and who was in fact his grandmother’s boyfriend, Jack, who rented a room in her hotel in Monahans, Texas.

When Jack died Clark wrote the song, which tells the tale of an unlikely friendship between a boy and an ageing, journeyed Texas oilman. “We was friends, me and this old man/Was like desperados waiting for a train”. Jack had been a wildcatter in the oil fields of West Texas, and had drilled some of the first oil wells in South America and the Middle East in the ‘20s, and Clark looked up to Jack as some kind of a hero. He is on record as saying that all the events in the song happened: “an old school man of the world/He taught me how to drive his car when he was too drunk to/And he’d wink and give me money for the girls….” By the end of the song, the boy is grown and the old man is gone. To quote Clark “He was just a crusty old bachelor who lived life on his own terms.”

The Highwaymen enjoyed great success with this song, peaking at #15 on the Billboard Hot Country Singles & Tracks chart on release, and the song always drew great attention and applause every time they played it live. It is easy to see why; they were a troubadour band, and this is truly a troubadour’s song.


About Russell Murphy 65 Articles
Can't get enough of this Americana stuff. Live or recorded, it's all good to me....
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