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WEBMISTRESS speculates:
This song wasn't written by Lindsey [Apparently it was some kind of "old slave spiritual" or something], so I can't read too much into it. But I can speculate as to why he picked it. I think it was because it highlights the contrast between being rich and being happy - the same reason he covered Satisfied Mind. As he says, "Only one thing money can't buy - true love that will never die." And now he's left alone with all his money, but "all [his] sorrows" too. Now, I don't suppose Lindsey is too sorrowful nowadays, but it wasn't his money that cheered him up, so the theme of the song still holds.
CHAR speculates:
This is the actual interview! [from Lindsey's Out of the Cradle video]...Lindsey is explaining how he chose that song to the press: "All My Sorrows"...is a Kingston Trio song...I am fairly sure it was...well probably...an authentic slave song. I changed the melody and chords to make something a little bit jazzier!"
"Also, one of the members of The Kingston Trio had died of cancer the year I chose to do that [song]...Dave Guard, who was the leader of The Kingston Trio...and a friend of mine...and I just thought that would be nice for him!"
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Bless his heart...I admire Lindsey so much! He is such a nice guy! The song breaks your heart as he strums a ukelele and his tour band plays along with him and sings the tune so well, in perfect harmony with Lindsey!!! A sad little OOTC moment !!!