
After a cursory, thoroughly unscientific survey, I have concluded that one of the longest, weirdest chord progression in rock music is found in “His Kingly Cave” from Frank Black and the Catholics’ “Devil’s Workshop” (2002).
While certainly there are upward and downward deviations, the preponderance of rock and pop verses follow a three- or four-chord pattern spread over four, eight or 12 bars. (See, for example, virtually every Pixies song.)
In contrast, the verses of “His Kingly Cave” cram 14 chords (10 of them unique) into a 13-bar format. Exotic chords with weird fingerings, no less. Perfectly mystifying for a song about dropping acid at Graceland.
If “Cave” represents an extreme but successful aberration, what’s an example of an unsuccessful one? How many chords is too many? This is partly a question of what separates a rocker from a jazz douche. But really it’s a question of musical effectiveness. How far can you extend a progression before it becomes self-indulgent, unfollowable, unpleasant?
Here’s how the “Cave” verse is constructed and why I think it works:
The first eight bars conform to the G minor scale. Bar 9 (Fsus2 to F Major) is the gateway to another harmonic world. The final four bars revolve around the peculiar F Byzantine scale.
G minor and F Byzantine have three notes in common — F, A and C (Bb too, but that’s not important here). In other words, both can be used to build a plain vanilla F Major triad, which is what brings the progression to its conclusion and links it back to the more familiar ground of the first eight bars. So while the Byzantine scale’s sudden appearance seems to intensify the acid trip, it talks you back down just as quickly.

Exhibit A: Components of the verse of “His Kingly Cave.” Listen here.
Some other long chord progressions:
Coffee and TV – Blur
8 bars; 8 chords
B Am E(add9) E
G G/F Bb Db (2nd time: A)
Hallelujah – Leonard Cohen
16 bars; 16 chords, 5 unique
C Am C Am F G C G
C F G Am F G E Am
Jabberwocky – Daniel hales, and the frost heaves.
11.5 bars; 17 chords, 6 unique
Fm Cm Dm Ab
Fm Cm Dm Bb
Dm Bb Fm Cm
Dm Bb Dm Ab G
Blackbird – The Beatles
8 bars, 18 chords, 11 unique
G Am7 Bm(b6) G
C Em D F#m Em Eb
D Em C Cm Bm A7 D7sus G