Before giving this song a listen, think about where Rock music was in 1968, the year this song appeared on the debut album of The Band. In ’68 everyone I knew was listening to Cream, The Jimi Hendrix Experience, etc. Sure, there was also Buffalo Springfield, The Byrds, and a few other Rock Groups incorporating Country elements into their music, but nothing like the Hard Country of a Lefty Frizzell song.
Hard fans of The Grateful Dead always claim that band wasn’t playing "catch-up" when they recorded and released their Workingman’s Dead and American Beauty albums in 1970, but in ’68 and ’69 they were still deep in Psychedelic territory, with their Anthem Of The Sun and Aoxomoxoa albums. After The Band’s 1969 second s/t album---routinely cited as the first "Americana" album---sent shock waves through the Rock music world, suddenly The Dead---and a lot of other bands---followed suit, but none with the depth The Band possessed and exhibited.
"Long Black Veil" had been a Country & Western hit by Lefty---cited by Merle Haggard as a major influence---in 1959, but it was new to me when in 1968 I heard Music From Big Pink. What an odd choice for a cover song, ay? Brave, daring, and evidence of a deep-rooted sense of identity.
The Band---then still known as The Hawks---spent all of 1967 in the basement of the Big Pink house with Bob Dylan, recording all manner of songs. I’ll bet this was one the fellas worked on. Absent was drummer/singer Levon Helm, who had quit The Hawks part way through the Dylan world tour of 1965-6 (two guys I was later in a band with saw Dylan & The Hawks in the San Jose Civic Auditorium, the rat bastards 😉), no longer wanting to be in anyone’s back-up band, nor playing for booing audiences. He went down to the Gulf Of Mexico and worked on an oil rig, that job ending when bassist Rick Danko called Levon to tell him Capitol Records had offered them a million bucks to record an album. Levon was on the next plane to Upstate New York. 😊