What songs do I put on a mix CD that will move my intellectual appreciation for jazz to the start of a true love and understanding?

It depends on how large your mix will be, how deeply you'd want to know about any one subtopic, but having just done a compilation of sax greats for a nephew, I'll include the jazz highlights here: Bongo Beep—Charlie "Bird" Parker Lush Life—Peter King Ghost—Joshua Redman Afro Blue—John Coltrane Now's The Time—Charlie "Bird" Parker Tangerine—Eddie "Lockjaw" Davis My Favorite Things—John Coltrane Blue Rondo A La Turk—Dave Brubeck Quartet (Paul Desmond on sax) Indian Song—Joshua Redman Feat. Joe Lovano Straight No Chaser—Peter King Stardust—John Coltrane Take Five—Dave Brubeck Quartet Chasin' The Bird—Charlie "Bird" Parker One Down, One Up—John Coltrane Jazz covers so much—I could easily write one answer just for singers, one just for each of a half-dozen instruments. The neat thing about digging into jazz from the perspective of just one instrument is that you can start to see similarities and differences, and I think that might be key for moving jazz (in your mind) from a strange jumble of notes to a genre you can really understand.

Start with "Kind of Blue" - Miles Davis (All Stars). From this album, you'll hear Bill Evans, Paul Chambers and John Coltrane. If you develop an ear for Bill Evans, Miles Davis and John Coltrane you are heading the right direction.. Otherwise get Louis Armstrong you cannot go wrong with that.

The start of a true love-  Ahmad Jamal Live at the Pershing is one not to miss.  Poinciana evokes the same sunny feelings as sitting around on a breezy day at the beach.  Bill Evans Sunday at the Vanguard is akin.  Very accessible to the ear. If that love is a fiery, go with the power of Freddie Hubbard and Coltrane, or Cannonball Adderley.  They did great cover albums, if you wanted to start with something familiar (Cannonball- Fiddler on the Roof Coltrane- My Favorite Things).  The Miles Quintet is a seminal group in jazz history. Regarding accessibility- Jimmy Guiffre and Bill Frisell. Both are great with a down home tinge. For understanding- study some music theory, transcribe a simple solo, try to figure out what is happening.  Listen to individual parts, listen to how they interact as a whole.  Try to play an instrument, take some lessons, practice.