Regarding the Herbie thing, yeah sometimes we just get bored with what’s obvious, and want to push ourselves and the listener.
Related, here’s a short pdf I made for my students with some (imo) important considerations for getting started with comping for jazz standards and some of the common variables: https://drive.google.com/open?id=1-944yuSdDVBTeWrM1uhziscE0nnOZtDz
An excerpt:
Some considerations about being ‘obvious’
- Clearly playing the root notes helps establish exactly what the chord is. Maybe you want to do this because you want the sound, and the harmony, to be very clear. Maybe you want the people you are playing with to be very aware of which chord you are playing, so they know where you are in the form. Maybe you don’t want to sound as ‘obvious’ and want to trust that either the other players, or the audience, or both, don’t need such strong indications of the harmony, and can enjoy a looser interpretation of the chords
- Similar things can be said of other issues. For example, if there is no bass player, you can fulfill that role and play low notes. Or you can leave the low register ‘blank’ and not feel the need to create a clear bass line. This is acceptable, it may simply be asking more of your audience, or of the people you are playing with.
- There’s nothing wrong with ‘comping’ with ‘single note’ chords
- Similar to #3, depending on context, you may need to include less and less information about the original chord. If the people you are playing with know the tune very well, and everybody involved has a strong sense of the form of the tune and is keeping the same sense of time, we do not necessarily need to spell the harmony out in obvious ways. For example, depending on context, simply playing the 9th and 6th together of a minor seventh chord can be enough to support that chord even though your voicing has none of the original notes of the m7. This is the kind of thing that makes more sense the more you play with people, and will be more or less applicable depending on the style of comping you prefer, or that you feel supports the soloist best in that context