An oft overlooked Miles record, and one of my personal favorites, is My Funny Valentine. It’s a live recording of the ballads and mid-tempo numbers from a '64 concert at the Philharmonic Hall. It was shortly before the second great quintet was completed with the addition of Wayne Shorter so the band features the core of Hancock/Carter/Williams and George Coleman on Sax.
Apart from All Blues (for Kind of Blue obvs) the pieces are all standards that Miles would return to repeatedly throughout his career so its a really interesting way of charting his development by comparing to earlier performances.
The quality of the recording is astounding (some say its one of the greatest concert recordings of all time) and the depth and the lyricism of playing is enchanting. I could listen to Miles’ solos of Stella by Starlight for hours.