Originally published July 19, 2025
The Grateful Dead classic "Friend of the Devil" is a fun song to improvise over, and this lesson walks you step by step through how I prepared to perform an improvised solo on it at a recent gig.
The 7-page PDF written version of the lesson is available above, along with the backing track in Boss and Ditto+ formats. Silver members can read the lesson on this page too, ending with a backing track player that takes a new pentatonic scale for every chord, so you can watch the gear shifts while you play over them.
What follows is the written lesson — the full contents of the PDF handout, so you can read it here or download it above.
I’m a relative newcomer to the Grateful Dead, but as you might imagine, many of their songs are fantastic training grounds for improvisation. My Monday night jam group1 has been playing “Friend of the Devil” for a while, and it’s relatively easy to solo over. In our weekly jams, I would often just wing it with a couple of pentatonic scales and trust my ear to create melodies and hit chord tones here and there. This is easy to do with the Form 1 G major pentatonic at the 12th fret—finding chord tones by imagining that the 12th fret is the nut and visualizing corresponding cowboy chords in that area.
When our group was invited to perform at a charity fundraiser recently, I decided to dig a little bit deeper. Improvisation doesn’t have to be an all-or-nothing affair. Many great improvisers stay close to a song’s melody or anchor their solos with composed segments. This is especially true in rock music, where audiences often want to hear a solo that sticks pretty close to the original recording, but not necessarily reproducing it note-for-note. In any public performance, it’s a good idea to do your homework and have a game plan.
In this lesson, I’m going to walk you through how I prepared for a mostly-improvised solo on “Friend of the Devil.” These techniques will work well on many songs, so don’t think of this as a lesson about that song, but rather as a “how to ‘plan’ an improvised solo” lesson.
The solo section is played over the chords of one verse (4 bars) and one chorus (6 bars). There are just four chords: G, C, D, and Am:
If we mark these chords on a cycle-of-fifths chart, we can see that all four chords fit into three adjacent wedges:
“Friend of the Devil” cycle-of-fifths chart
Any time that happens (and it happens a lot), we can immediately pull out the Nashville numbers for the chords using this decoder ring:
So for this chord progression, we would treat G as the I (1), C as the IV (4), D as the V (5), and Am as the ii (2-). It’s not always the case that the I (1) chord sounds like the tonal center, but in this song, it does. That means that the G major scale (or G Ionian mode) contains all of the notes of all four chords, and we could use it to solo over the entire chord progression.2
When all of the chords from a chord progression fit a single major scale mode, I usually find it easiest to use the Pentatonic Gear Shifts approach. For full details, check out the Improv 101 course or the Gear Shifts YouTube video and corresponding Patreon lessons.
The basic idea is that the three major chords and three minor chords in the key form three pairs of pentatonic scales, with the scales in each pair sharing the same notes. I refer to the pentatonic scale corresponding to the I (1) and vi (6-) chords as the neutral position. In this case, it’s the G major pentatonic scale (equivalently, E minor pentatonic).
If you take any rectangle or stack shape from the neutral position and move it up one set of strings (taking the warp into account, of course!), you get a different pentatonic scale that contains the IV (4) and ii (2-) triads. I call this the “shifted up” position. Similarly, if you start with the neutral position scale and shift down one string set, you get the pentatonic scale that contains the V (5) and iii (3-) triads in the “shifted down” position.
Although each major/minor pair of pentatonic scales shares the same notes, the notes of the corresponding triads fall in slightly different locations, as shown here:
So, for example, when playing over the V chord, you would play the shifted-down pentatonic scale and emphasize the major triad target notes. Over the ii chord, you would play the shifted up pentatonic scale and aim for the minor triad target notes.
For me, there are two incredibly cool things about shifting pentatonic scales like this:
So for “Friend of the Devil,” we have this sequence of shifts:
| Measure | Chord | Function | Position | Shift |
|---|---|---|---|---|
| 1 | G | I | neutral | - |
| 2 | C | IV | up | +1 |
| 3 | G | I | neutral | -1 |
| 4 | C | IV | up | +1 |
| 5 | D | V | down | -2 |
| 6 | Am | ii | up | +2 |
| 7 | D | V | down | -2 |
| 8 | Am | ii | up | +2 |
| 8 | C | IV | up | 0 |
| 9-10 | D | V | down | -2 |
One handy trick to know is that if you need to shift up two strings, you can instead shift down two frets. And similarly, if you need to shift down two strings, you can instead shift up two frets. In this song, that trick will make the shifts much easier.
To warm myself up to play over this progression, I made a backing track and practiced improvising a different solo for each of the five starting positions of the G major pentatonic scale (i.e., Forms 1-5).
Each time, I would remain in that one position and shift up and down string sets (as discussed above) to change scales to match the chords. This helped me get used to the sounds of the three families of pentatonic scales in the context of this chord progression, and it ensured that I could play something sensible anywhere on the neck.
Building a flight plan
There are several things I usually try to keep in mind when outlining a solo:
For this solo, I decided to start low with a specific lick, gradually work my way up the fretboard, and stick the landing with a parallel-sixths phrase.
Opening move
In my group’s arrangement, the acoustic guitar solo follows an epic penny whistle solo. I decided I wanted to start my solo with a busy open-string lick that would instantly create energy and interest, and then the rest of the solo would be improvised, but within some guardrails. This is the G Ionian lick I opened with:
This is a variation of a lick that I remember first learning when playing “Crazy Train,” but I think of it as something you can play inside this 3NPS fragment3:
In the key of G major, G is the first scale degree, and placing this shape with the root at the open G string makes this sequence of pull-offs very easy to play.
At the end of the first measure, I planned to slide into the C note at the 5th fret of the G string, which is, of course, the root of the C chord. The C note makes an especially juicy target because it’s the only note in the C triad that hasn’t been played yet.
Bars 2-4
As mentioned earlier, when going back and forth between the I chord and the IV chord like this, only one note changes between the two major pentatonic scales. Specifically, the 3rd of the G major triad (B) moves up a half step to become the root of the C major triad (C). In these situations, it can sometimes be easier to change your mindset and stick to the G major pentatonic scale on both chords, making sure that you don’t emphasize the 3rd when playing over the C chord.
We could also use triad overlays on the G major pentatonic scale. It turns out that this is precisely the same shift that is used to play over the Am to F transition in the “Stairway to Heaven” outro, and we can use the same rectangle and stack shapes to visualize it. In “Stairway,” Am is the vi chord, and F is the IV.
Here are the targets for the IV chord (C) overlaid on the G major pentatonic rectangle and stack:
So, after my opening lick, I planned to stick to G major pentatonic for the next three bars and work my way up from the nut to somewhere higher on the fretboard. When the second C chord arrives, I planned to hit a good target using the IV chord overlays. In my live performance, I found my fingers on top of the G major stack rooted at the 8th fret of the B string, and I ended up landing on the C note at the 10th fret of the D string.
Bars 4-8
The second half of the solo alternates between D and Am (with one passing C triad that shares a bar— and a scale—with the Am triad). I decided to use gear shifts for those chord changes.
When I was practicing, I started out playing D major pentatonic (by shifting G major down one string). Then, I would shift the scale shape down two frets to play A minor pentatonic. This worked, but it felt slightly awkward repeatedly shifting down and then back up two frets each time.
Eventually, I decided to shift the scale patterns up and down two strings instead. When I first started using this technique, I found it challenging to visualize two-string shifts, so I created a set of Soundslice backing tracks specifically for practicing these shifts.
During the live performance, this section of my solo was entirely improvised, with no prior consideration given to target notes, but toward the end of the solo, I wanted to end up near the D note at the 10th fret of the high E string, so that I could close the solo with a parallel-sixths lick.
Sticking the landing
Parallel-sixths licks fit well with the country/folk style of “Friend of the Devil.” By ending the central part of my solo near the root of the D chord on the high E string, I set myself up to do some sliding sixths. This is one of the on-the-fly harmonization techniques I teach in my Instant Harmony YouTube video.
With any I or V chord, you can visualize an inverted major third starting on the root, followed by two inverted minor thirds. This is what I visualized:
And this is what I ended up playing:
This specific sequence of nine notes isn’t improvised per se, but you can certainly improvise when and where you use this technique.
Altogether, in my performance, I started somewhere specific, had a rough plan of how to get to my destination, and ended with something specific. I didn’t end up improvising the world’s greatest guitar solo, but it fit well with the chord changes, and I think it fit the style we were going for.
I encourage you to try out my flight plan for “Friend of the Devil” using the provided backing track and then try making up your own!
But also, as I said at the beginning, this lesson isn’t limited to improvising over “Friend of the Devil.” A wide variety of chord progressions can be handled with this exact type of analysis, and the Pentatonic Gear Change methodology can be extended to handle more complex chord progressions.
Friend of the Devil
G · 99 BPM · 10 chords · 24.2s loop
The backing track for the flight plan.
To learn why you should form an informal jam group, check out this lesson.
↩In a rock song with the same chords, a band like AC/DC might treat D as home, which would place this in D Mixolydian. Even in that case, the Nashville numbers would stay the same, because the Nashville numbers are always based on the parent major scale. Similarly, if Santana made it sound like Am was the tonal center, we could use the A Dorian mode, but Am would still be ii (2-) in Nashville notation.
↩It’s worth knowing that this lick also works on the 3NPS fragment where the 1st scale degree is the lowest note of the lower string, which has the exact same fingering.
↩
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