Jack Straw

The best Grateful Dead cowboy song

After spending their first few years writing abstract psychedelic tunes, the Grateful Dead took a hard turn into Americana. They wrote a bunch of songs inspired by blues, country and folk, and in doing so, they massively expanded their listener base. Several of these songs involve outlaws and drifters in the Wild West. I think the best of the Dead's cowboy songs, both lyrically and musically, is "Jack Straw".

When I was a kid, my older stepbrother had a bunch of Dead albums stored in our apartment. I avoided listening to them at first because their covers suggested that they would be too heavy and frightening for my tastes. Imagine my surprise when I finally did try them and they turned out to be affable psychedelic country. I first heard "Jack Straw" on What A Long Strange Trip It's Been, the hugely better of the two Grateful Dead greatest hits compilations. (The other is Skeletons from the Closet, which has some baffling choices - "Mexicali Blues", why?)

Bob Weir co-wrote "Jack Straw" with Robert Hunter, one of only a few songs they wrote together before they had a falling out over Bobby's tendency to change Hunter's precious lyrics. Bobby tells the story of the song in David Dodd's post about the song on Dead.net.

I had just read Of Mice and Men for about the tenth time. I was completely smitten by that story. I took a step back in time into the Depression, and that era, and this story emerged between me and Hunter about these two guys on the lam... ne'er-do-wells... victims of the Depression.

Dodd explains the song's narrative structure.

The two “ne’er-do-wells” are named in the song as Shannon (Garcia) and Jack Straw (Weir). Here’s how the dialogue shakes out. Note that besides the two characters, who each sings his own lines as appropriate, there is a third person, the narrator, who is sung by Weir, Garcia, and Lesh.

Narrator: "We can share ..."

Shannon: "I just jumped the watchman ..."

Jack Straw: "Hurts my ears to listen, Shannon ..."

The main character's name was probably inspired by the jackstraws in pick-up sticks. Here's Jerry using the term in the Woodstock documentary.

So that's the backstory and the lyrics. How about the musical side of the song? The structure is really odd, and the harmony is mildly unusual too. Before we get into any of that, though... what the heck is the tempo? Deadheads talk about the song's tempo changes, and it has them in the sense that the band speeds up and slows down, but there are also changes in the underlying pulse level. Is the song basically slow (around 70 BPM) with a lot of doubletime, or basically fast (around 140 BPM) with a lot of halftime, or both? Bobby counts it in at around 70 in live performances, but I can easily hear it either way. "Jack Straw" is not the only Dead song to have this ambiguous cut time; "China>Rider" has it too.

Here's my chart. The song begins with a four-bar intro on E and Esus4. Jerry enters with a melody that accents an awkward A-sharp but recovers gracefully, with that nice vocalistic bend from D-sharp up to E. The line "We can share the women, we can share the wine" is on a series of diatonic chords from E major: E, F#m, C#m, A. The A chord lands half a beat earlier than you were expecting it. The line "We can share what we've got of yours" makes a quick detour into E Mixolydian via Bm and D. The line "cause we done shared all of" is a bar of 2/4. The word "mine" moves through E, G#m, D and A. The move from G#m to D is especially ear-grabbing. It isn't just that G#m is from E major and D is from E Mixolydian; it's also a root move by a tritone, and a weird bit of neo-Riemannian transformation.   

The "I just jumped the watchman" section is where you would normally expect the prechorus, so that's what I called it. It's a groove on E7sus4 to E7 while Jerry is singing, then F#7sus4 to F#7 for Bobby's part. This part taught me what a 7sus4 chord is back when I was learning guitar. The last F#7sus4 to F#7 pair gets cut off early, forming another bar of 2/4, and moves into a loop of D, Bm, A and E7, putting us back in E Mixolydian. A normal song would go into the chorus here, but instead, the Mixolydian loop carries us through a six-bar guitar solo and on into the next section.

What should we call this next part? We're still waiting for a chorus, but "Jack Straw" doesn't have one. I still called it the "chorus" in my chart for lack of a better name. The loop goes until the line "not with alllllll", where there is yet another key change, to D major. This part alternates D and G before walking chromatically back down to E at the transition back to the intro groove. The tempo also slows down significantly here. The band has been gradually accelerating from a low of 64 BPM in the verse to a high of 74 BPM in the "chorus", and in the interlude before verse two it drops all the way back down to 65. The Dead can suffer from shaky timekeeping, but in this song, the variable tempo has a nicely expressive effect. Here's a tempo map I made of the song using Ableton.

"Jack Straw" perfectly illustrates the Dead's overall musical strengths and weaknesses. The writing is imaginative, and unconventional. The music is syncopated and groove-based yet contrapuntal. There's a dynamic fluidity to it that is greater than the sum of its parts. So those are the strengths. The main weaknesses are a cluttered and disorganized arrangement and the fact that none of these three guys can sing. Jerry at least has a charismatic slyness to his vocal style that balances his shaky pitch; Bobby and Phil don't bring much to the table but enthusiasm. Many Deadheads claim to find the weak singing to be an attraction; you feel more empowered to sing along if you know that the band can't sing any better than you can. Those songs are a lot of fun to sing, and while they are more complicated than most rock songs, they are still pretty attainable for hobbyist guitarists. So maybe we should be evaluating Dead recordings as templates for amateur participation rather than polished works.