I think that 3 albums from Duke Ellington will give a nice introduction to jazz.
The Great Summit - Duke Ellington and Louis Armstrong. There's a quote in Ken Burn's Jazz series by Wynton Marsalis to the effect that if you want to play jazz you have to go through Louis Armstrong and this album will show you why. The style here is that of an earlier jazz with overlays of New Orleans and Chicago.
Duke Ellington Meets Coleman Hawkins - this is the swing era of tight bands, brilliant arrangements, and blistering soloists. One of the most enjoyable albums I listen to.
Duke Ellington and John Coltrane - the music here is changing, shifting to a less traditional more abstract style. These are mostly Ellington tunes interpreted by Coltrane and his band of that era. Compare his solos here with what you hear on Kind of Blue.
Bill Evans had a strong, arguably dominant influence on Kind of Blue so I think you would enjoy his work on Explorations, Waltz for Debbie, or Portraits in Jazz.
Greg
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