When he told me the news about Mr Prine's death from Coronavirus complications, he reminded me that he and his mates had booked to see the John Prine show at the Palais after Easter - but it was cancelled when the 73 year-old singer caught the bug a while back and couldn't travel.
He likes his singer-songwriters, The Boss does: he reckons Prine was up there with Bob Dylan and Leonard Cohen, Joni Mitchell and Jackson Browne, Van Morrison and Bruce Springsteen.
I didn't care for his raspy voice, myself - reminded me of a Wood Duck gabbling to its pals - but The Boss says a Wood Duck can't put it's finger on the essence of things.
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"His song Sam Stone, about a Vietnam war veteran, was the saddest song of my generation, General," he says. "It has some lines you can never forget, like
There's a hole in Daddy's arm, where all the money goes...
"And his song Paradise was one of the first to rail against tearing up the planet, when his beloved Green River in Kentucky was mined and "Mr Peabody's coal train has hauled it away."
Then the coal company came with the world's largest shovelAnd they tortured the timber and stripped all the landWell, they dug for their coal till the land was forsakenThen they wrote it all down as the progress of man
"And a Wood Duck doesn't have a sense of humour either, General. Prine wrote some very funny songs over the years. Most of his songs tell a story - and we all like stories.
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He told me Prine left school to become a mailman, joined the army for two years and returned to his old job, composing tunes as he did his rounds. He was playing minor clubs around Chicago when Kris Kristofferson heard his original compositions and helped him land a recording contract.
Although none of his albums ever topped the charts, many of his songs were covered by well-known artists, with the Everly Brothers covering Paradise and Joan Baez and Bette Midler covering Hello In There. Bonnie Rait made Angel From Montgomery famous and Prine went on to record many duets of country tunes with the likes of Bruce Springsteen, Kacey Musgraves, Emmylou Harris, Alison Krauss, Mac Wiseman and Lucinda Williams.
You mightn't think I know anything about these people but I can tell you, The Boss has forced me to listen to them when he's been carting me around in the car. At least, most of them sound better than John Prine - I like Bonnie Raitt and Emmylou Harris myself. And Dolly Parton too.
I guess he's trying to make up for missing out on his concert. That means he can stay home and do things with me instead, which has to be a good thing, although I've noticed when he has to stay home at times like this his mood doesn't necessarily improve.
At least Prine sings those funny ones and it perks The Boss up right away. He said John Prine had a few serious health issues over the years and seemed to regard every extra day on earth as something of a bonus.
On his last album he sang a song called When I get to Heaven which The Boss is playing quite a lot, so I thought I would inflict it on you too. Woof!
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