Hey Smole 
If you are new to transcription I’d recommend the following criteria for choosing a tune to transcribe from:
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A tune that you can already play and have memorised the chord changes
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Something that contains lot’s of 25s and 251s, any 251 lines you transcribe are immediately transferable to many other tunes
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I think a medium tempo tune is always good too.
Based on that criteria, here’s a record I would suggest to you:
The form is simple, we have covered it in many lesson on PianoGroove. The form is also very repetitive, mainly consisting of 251s in Bb Major, and G Minor.
Here’s a process for you to follow Smole:
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Play along with the record, just play left hand voicings underneath and listen to how Wynton adds to the melody, takes notes away, changes it, rephrases it, and ultimately adds more character and personality.
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A simple exercise could be to work out the melodic decoration he plays over the head of the tune which is from 0:05 to 0:53 second. There is that nice thing he plays at 0:38-0:41, but eveything else is just slight tweaks to the melody. If you know the tune, and know the melody, you should be able to figure that stuff out no problem. It will take work, but it is much easier that transcribing his solo because you know that he is simply adding to the original melody.
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Next notice how he transitions into his solo which starts in the last bar of the head 0:53 - i always pay attention to this transition from head to solo, it’s usually anticipated and starts in the final measured of the head.
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From 0:54 to 1:07 is the first A section of his solo. If you know the tune/changes (which you must do before transcribing!!) the you will know that it follows:
C-7 / F7 / Bb7 / Ebmaj7
A-7b5 / D7 / G-7 / % /
Just start with that 13 seconds of music. That is your exercise. I will do it too when I’m back at the piano on Tuesday. @kim22 … you might be interested in this too as I remember you asked about a transcription exercise.
First I always play the left hand voicings underneath the record so that I can hear exactly where his lines are starting and ending, and where his improvised notes and ideas are falling in relation to the underlying chord changes.
At first, it might have taken me a week, a month, whatever it took, I just worked out every single note so that I could play along with his and imitate his style flawlessly.
I promise you that just those 8 bars will teach you more about swing and rhythm than anyone can communicate verbally. Ultimately it’s a feeling, that’s why they call it ‘swing feel’.
@smole - you definitely have the ability to transcribe from records like this.
I’ve always been hesitant to ‘prescribe’ songs that students should transcribe from, but hopefully my tips above can put you in the right direction.
The whole point is that we choose things that we personally like, we transcribe from them, and that gradually develops into our own sound.
Cheers!
H