When I was a kid, some of the very first things I transcribed were Ace Cannon tunes (50s-60s R&B) - the heads and the simple solos. I didn't know how to write the rhythms back then, so I just did stemless note heads and memorized the rhythms.
Try to work in small chunks, like 4 notes at a time for example, where you can hear scale fragments, arpeggios, enclosures, etc. Soon you'll start to recognize the harmonic context, like, that phrase starts on a major 3rd, or that high note is a ninth. To recognize where things fit, listen to the bass line to get the roots of the chords. Try to learn a few fragments (licks) and understand them without even writing anything down at first.
Transcribe by time, not by musical goals in the beginning.
Make 10 minutes your goal each day for a week. You will get the idea, not get frustrated, and get better at it! Try to play tunes you know at first in different keys. Twinkle twinkle, happy birthday, etc.
Transcribe Hank Mobley or Miles......great place to start with jazz
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