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Calling all theory nerds!!

OK.
It means that you are not playing 9 but playing b9.

More about that question playing Locrian #1 or Locrian #2 scale.

From a very serious source, of a very knowledgeable Musician, Don Kasper.
From here:
Anyone have a harmonic analysis of Stella by Starlight?


"For example, in the first measure, Emin7b5, try hearing and incorporating an F#(the natural 9) in that chord, as well as the following A7b9 (now with "13!"). That F natural in the Emin7b5 is not a pleasant note, IMO - the F#, is, to my ear, a note that should be heard and explored melodically, as well as harmonically. Abiding by the key signature and melody, only, may delay this discovery. Try it at a piano and see if you like the F or the F# in that Emin7b5 chord. In the A7b9 chord, the F sounds great, as well as the F#. Any experienced jazz pianist or guitarist (IME) would not play the F in the Emin7b5 chord, but might play either the F or F# (or no "F" at all) in the A7b9 chord."
I am most definitely going to try this out on my keyboard to see what you mean. Thank you for your educating...that's exactly what I was hoping for when I started this thread.
 
Another question.
In Measure 7 with Ebmaj7 chord
(based on Eb major scale as)
Ebmajor.PNG


You play A natural in Measure 7 (per Damien).
Are you playing 11 or #11?
 
If you look at measure 15, you will see that the chord is notated the same way as in measure 7. However, in measure 15, he specifies that you are playing the #11. So I'd say measure 7 is a typo, which left out the #11 in the chord spelling.


In Measure 1, we have the Emin7(b5) chord. In Measure 2, we have the A7(b9) chord.
Someone could "assume" that we have that ii-V - i "structure" resolving in D minor, and...
Someone could "assume" - it's the D harmonic minor scale, but...
Damien has indicated to play C natural.

dhmsc.PNG
 
In Measure 1, we have the Emin7(b5) chord. In Measure 2, we have the A7(b9) chord.
Someone could "assume" that we have that ii-V - i "structure" resolving in D minor, and...
Someone could "assume" - it's the D harmonic minor scale, but...
Damien has indicated to play C natural.

View attachment 4100510
I see your point but usually, an exercise is just an exercise. When you're first learning this stuff it's typically best not to get too tricky right out of the gate. In this case, you don't have to assume it's harmonic minor.

My general rule for approaching something new is, "don't make it harder than it has to be".
 
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I see your point but usually, an exercise is just an exercise. When you're first learning this stuff it's typically best not to get too tricky right out of the gate. In this case, you don't have to assume it's harmonic minor.

My general rule for approaching something new is, "don't make it harder than it has to be".

Don't get me wrong.
If I don't understand it - I STOP.
Next two measures of Cmin7 (or Cmin11) and F7 looks like another ii - V - I (with Bb major as I), but...
It changes in Measures 5, 6, and 7. It's another ii - V - I with Eb major as I, and so on.