Thelonious Monk composed Ruby, My Dear for his first love, Rubie Richardson. I first heard the song when I about twelve. At that point I was listening to jazz, but nothing like this. Monk’s complex chords and melodies floored me. This song was where I discovered Monk. There are a lot of recordings of Ruby, My Dear but my favorite is this one, with Monk and John Coltrane together. Coltrane’s forceful melody with Monk’s introspective chords are sublime.
If you’d like to hear me play Ruby, My Dear, today’s your lucky day. I recorded this in Garage Band with my Yamaha MIDI keyboard. I didn’t get cute and fix any notes. I just pressed the red button and started playing. It’s not particularly good but was played with a lot of love for this song and Monk.