The Wild West-Inspired Lyric Bob Dylan Wrote with Multiple Twist Endings

If you’re a pretty good songwriter, you might be able to effectively tell a story with several moving parts over the course of a single composition. Or you might be able to provide an insightful character sketch, getting inside the head and heart of your song’s protagonist.

In “Lily, Rosemary and the Jack of Hearts,” released in 1975 on the masterpiece Blood on the Tracks, Bob Dylan gives us at least three separate character sketches, all while telling a thrilling story of deception and violence set in the Old West. And, just for kicks, he throws in a couple twist endings to boot. Just another day at the office for a songwriter for the ages.

A Deviation from the Theme

When people look to shorthand a description of Blood on the Tracks, they often call it a “breakup album” or a “divorce album.” Bob Dylan has always vehemently denied writing the songs on that record about the marital struggles he was enduring with his first wife Sara. But it’s hard to hear the frustration and pain dripping from the lyrics of most of those songs and not think there was something deeply personal at their heart.

What then to think of “Lily, Rosemary and the Jack of Hearts”? Blood on the Tracks is cohesive, both in the sound of the record (despite Dylan compiling the material from two diverse sets of sessions), and considering the prevailing lyrical theme of tortured love.

You could kind of consider “Lily, Rosemary and the Jack of Hearts” to be a lyrical cousin to the material on the album, although the motivations of the main characters generally don’t have much to do with romance. As for the hoedown-style musical presentation, that’s a definite departure from the rest of the record.

And yet, Blood on the Tracks wouldn’t be quite the same without this epic. It’s an album where Dylan’s songwriting ambition and achievement hit levels they hadn’t reached since the mid-’60s. “Lily, Rosemary and the Jack of Hearts” represents that return to elite form in the best possible way, especially when you dive into the song’s lyrics.

Exploring the Lyrics of “Lily, Rosemary and the Jack of Hearts”

If you’ve never heard the song before, you might need several listens before you actually catch everything that’s happening. The basic story concerns the three titular characters and Big Jim, who is, in a way, the antagonist of all three. Their fates meet in some dusty, 19th-century Old West cabaret, all while a strange drilling sound is hardly noticed by anyone but the songwriter.

Dylan masterfully brings these characters to life with just a few details and facts about their past. Rosemary (Big Jim’s wife): She had done a lot of bad things, even once tried suicide / Was lookin’ to do just one good deed before she died. Lily (Big Jim’s mistress and a performer at the cabaret): She’d come away from a broken home with lots of strange affairs / With men in every walk of life which took her everywhere. And Big Jim: With his bodyguards and silver cane and every hair in place / He took whatever he wanted to and he laid it all to waste.

The Jack of Hearts mostly remains an enigma, but he’s the catalyst that drives the action. It’s action that Dylan foreshadows but never actually shows. Only in the aftermath do we realize (spoiler alert!) that the Jack of Hearts is using both women to fell his enemy, Big Jim, by coaxing Rosemary to stab her husband to death right before Jim is ready to shoot the Jack for dallying with Lily.

That’s why it was telling that, earlier in the song, Rosemary was drinkin’ hard and seein’ her reflection in the knife (the same knife she’d use to kill her husband). Since she’d already tried suicide, it makes sense she’d be willing to face hanging. But why in this circumstance? Many have speculated that Lily could be the illegitimate daughter of Rosemary and the Jack of Hearts, and that this was their way to protect her from Big Jim’s cruelty. (That would explain the broken home of her childhood and Big Jim believing that he’s seen the Jack as a picture upon somebody’s shelf, probably Lily’s.)

In any case, Dylan throws in one more twist: The drilling in the wall was perpetrated by a gang pulling off a bank job, and the Jack of Hearts, as their leader, used the distraction of the murder to help them get away with it. The song ends with Big Jim dead, Rosemary preparing to die, Lily contemplating her next move, and the Jack of Hearts long gone.

A couple of ambitious screenwriters have tried to wrestle the narrative of “Lily, Rosemary and the Jack of Hearts” into a film script, but nothing has ever come to fruition. It’s probably for the best. After all, Bob Dylan filled in all the blanks of the story in thrillingly satisfying fashion in a little under nine minutes, and in the process, he created an awards-worthy movie in our minds.

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