The trio of Dylan albums/recording sessions that include Self Portrait, New Morning, and Dylan read to me as Dylan investigating what makes a song and what were the techniques that other songwriters were using. This helps explain the wide range of material that he investigates, material that includes both traditional songs and the work of his contemporaries. These records are a continuation of the exploration of American music found on The Basement Tapes, with Dylan's takes on traditional songs alongside songs by Gordon Lightfoot, Paul Simon, Jerry Jeff Walker, and Joni Mitchell.
'Lily of the West' is based on a traditional broadside ballad that was sung in both Great Britain and Ireland, with some of the lyrics adjusted to fit the locality. It's a ballad about love gone wrong, as they say, with cheating and murder on the bill of fare. It seems to have appeared in the late 1890s, travelling to North America where it was adapted and grew in popularity. The folk magazine Sing Out! says this about the song's history: “This old ballad has been kept alive over the centuries by both print and oral tradition. Originally an English street ballad (or broadside), the song became particularly popular in the United States by parlor singers and ballad-printers." The ballads were handed down from performer to performer, so that inevitably there were numerous variations, even as the song was collected in printed format. For example, there are versions where the narrator is set free at trial, either because of a technicality or due to the testimony of Flora.
Bob Dylan, ‘Lily of the West’, from Dylan (1973)
The song seems to have undergone a revival during the folk period of the late 1950s and early 1960s. New York singer Bob Gibson, who recorded the song, was an important figure in the movement. Gibson's website, created and maintained by his son, gives a good idea of Gibson's role in bringing attention to American folk music:
"Bob Gibson was a devilishly charismatic choirboy in the midst of the fray as folk music was wrestled from the historical purists and redeemed as a popular art form. He was one of the redeemers. His repertoire and his life story reflect the contest between light and dark." https://www.bobgibsonfolk.com/story/
Gibson had met Joan Baez when the two played at Chicago's Gate of Horn club. He told her that she should come to Newport that July where the first Newport Folk Festival was being held. On July 12,1959 Gibson invited the eighteen year old Baez onstage with him, and together they sang "Virgin Mary Had a Son" and "We Are Crossing The River Jordan."
Irish singers Jesse Owens and Anne Byrne performing ‘Lily of the West’
Baez first met Bob Dylan in 1961, and she was already well known in the folk movement and beyond. She helped his early career by introducing him to her audience. He was certainly aware of who Bob Gibson was and the traditional songs that he was recording and making popular. When Dylan was later investigating and recording a lot of traditional songs, he recorded two that Gibson had recorded as well--'Lily of the West' and 'This Evening So Soon', which Gibson recorded as 'Tell Old Bill'.
Dylan's version of 'Lily of the West' was released on Dylan, a compilation of outtakes from New Morning and Self Portrait that Columbia released, without consultation, after Dylan departed for Asylum Records. "Lily of the West" was recorded on June 3, 1970 during the New Morning sessions. Musicians were Bob Dylan (vocal, guitar, harmonica & piano), Charlie E Daniels (bass), David Bromberg (guitar, dobro), Ron Cornelius (guitar), Al Kooper (organ), Russ Kunkel (drums), and unidentified background vocalists.
The background is somewhat generic, unembellished, and over this Dylan intones the song with lyrics fairly matching the versions that Gibson and Baez had previously recorded. The use of the backup chorus is a novel and somewhat strange aberration for Dylan, although he would revisit it for Street Legal and his Christian albums. It's a song that references the American west lyrically and in terms of its musical style and it is part of a western theme that becomes prominent with Dylan around this time. It's worth noting that this was the same period during which Dylan created music for Sam Peckinpah's film Pat Garrett and Billy the Kid as well as being cast in the role of Alias, a mysterious character perfectly in keeping with Dylan's love of games of identity. During filming he moved to Durango with his whole family; by all reports his wife Sara was miserable there.
The woman's name in 'Lily of the West' is Flora (in earlier versions it was Mary or any of another half dozen or so female names) but Dylan's identification of the song with the American west (the lyrics place the song in Kentucky) and the arrangement wherein the background singers echo the title, makes the name of Lily every bit as prominent, perhaps more so. Flora is the Lily of the West, not Lily of the West, but the listener hears the name and not the flower association. One cannot help but wonder if the song was in some way, consciously or not, part of the inspiration for "Lily, Rosemary, and the Jack of Hearts" from Blood on the Tracks.
Bob Dylan, “Lily, Rosemary & the Jack of Hearts” from Blood on the Tracks (1975)
It has been mentioned by more than one writer that 'LRJH' is the black sheep of Blood On the Tracks. Not because it isn't worthy of inclusion on the album but because it is a story song told in straight narrative, unlike other songs on the record ("Tangled Up In Blue," "Shelter From the Storm") that fracture their narratives reflecting the 'outside of time' songwriting methodology Dylan was using at the time. It's also clearly set in the historic American west while the rest of the record seems contemporary.
What Dylan learned from 'Lily of the West' was largely how to sing it in order to best tell the story. He had been writing story songs since the beginning, 'talking blues' like 'Talking World War III Blues' and 'Bob Dylan's 115th Dream', though these songs often utilized surrealistic and psychedelic imagery as well as absurdist humor. But it seems as though there's a point that Dylan becomes interested in just investigating and playing with songs written by other people, learning about narrative and detail. The basement at Big Pink was a laboratory for Dylan, and the various musicians of The Band, talented as they are, provided a different lens with which to look at songwriting. Dylan appears to test drive the idea with several story songs that are meant to be naturalistic portrayals of events on John Wesley Harding, the album that draws a line in the sand between his wordy, surrealistic amplified rock and the more mature songwriter who was to come.
Bob Dylan, “Lily, Rosemary & the Jack of Hearts”(Take 2) from the 1974 ‘Blood on the Tracks’ New York City sessions
The action of both stories involves murder. In 'Lily of the West' it is straightforward, with the narrator stabbing his rival for Flora's affection. In 'LRJH' the relationships are a bit more involved. Like Flora, Dylan's Lily is not innocent. She has had some kind of relationship with the Jack of Hearts, and she is having an affair with Big Jim, the town's richest power broker, who is married. Like Flora, Lily lives by her own set of rules. Big Jim is prepared to carry out the murder of the Jack of Hearts by shooting him, but it is his wife Rosemary, the other woman in this story, who commits the murder by stabbing Jim in the back with a penknife. Her act is more than just the murder of an unfaithful husband, there are altruistic motives as well: she saves the life of the Jack of Hearts and she offers Lily a chance at happiness. "She was looking to do just one good deed before she died."
Of course, things don't end up that way. Rosemary is executed the very next day. As for our Lily, the future looks uncertain. Her career at the cabaret is likely over--'Lily had already taken all of the dye out of her hair.' She's alone, thinking about her life and her father and of Rosemary's final act. And the Jack of Hearts? He is nowhere to be seen, having left behind Lily, the town, and the entire sordid scene. We don't know if he met up with his gang of thieves who have robbed the bank two doors down from the cabaret (a subplot of the song), but he is the 'only person on the scene missing'--in other words, he's not there, but the buzz around him is everywhere. Which is a pretty good description of Bob Dylan in the early seventies.
It seems as though once Dylan emerged from the trauma of his motorcycle accident he became, like Bob Gibson, 'one of the redeemers,' who sought to rescue not just folk music, but popular music in general, from the 'historical purists' and return it in a living form to the people. He became a student of songwriting of the highest order, which continues to this day, highlighted by the upcoming (November 2022) publication of his book The Philosophy of Modern Song, a collection of more than 60 essays on other songwriters' work. In his 1978 review of Dylan's film Renaldo and Clara for the Village Voice, Richard Goldstein writes: "It’s been Dylan’s contention (since Nashville Skyline) that rock is American pop music which ought to be accessible to great numbers and varieties of American people."
That's part of the reason that the 'transitional' period of 1969-1974 may be one of Dylan's most interesting, now that the cultural dust has settled on the sixties and seventies: it set the table for the rest of Dylan's career, and it demonstrated that he was becoming much more than a folk singer or a counter cultural hero. He was becoming a serious student of the art and craft of songwriting.