‘Ask Me Now’ is a prime example of the difference between “Theoretical Analysis” and what we are calling “Preparational Analysis” (Link). Looking through any number of lead sheets and transcriptions of this piece will show many different chord names. The first bar, for instance, might show Gm7, C7, F#7, B7 all in one bar! Although there is some logic to this if you think of the B7 as a tritone substitution for F, the information is all but useless if we are trying to prepare ourselves for improvisation.
Unfortunately, we will never know how Monk thought about these chords but I have learnt that the best place to start with a Monk tune is by analyzing the left hand and more precisely the bass movement. Example 1 shows us a stripped down version of the left hand of the A section. The next part is the left with the melody notes that occur on the first and third beats. The last bit is the whole thing with a Db major scale played over the chord shells. Listen and see what you think.
Example 1
For me, this analysis turns the song into a manageable series of changes. It makes sense to think of the song as being in the key of Db (we leave it without a key signature because it is easier to read). The changes are a series of half and whole steps with two ‘five ones’ – Eb-Ab, Bb-Eb, and finally a II-V-I (Eb-Ab-Db) to finish the eight bars.