I think md had a good rec, and the album info here from Mike and Ron is spot-on. My favorite Miles Davis album was Kind of Blue and I still have that cassette loaded in the X5 for long road trips.
If you're getting into the jazz, give Grant Green a listen sometime. Start with "Cantaloupe Island" and then listen to the rest of
His Majesty King Funk and your son will have no problem dancing at the h.s. prom