Jazz is a huge genre with styles ranging from big band sounds of the 30's to contemporary stuff. I listen to contemporary stuff say 50's and later and more specifically I stick to the sound of smaller bands (trios, quartets) with bass, one maybe two horns, vocals and drums. I do not listen to big bands. I especially like women vocalists. This is my taste and along those lines here are some stuff to listen too.
- The Bill Evans Trio. The Waltz For Debby album on HDtracks is wonderful and sounds awesome.
- Miles Davis. Kind Of Blue and Milestones in particular. Many consider Kind Of Blue one of the best Jazz albums ever.
- Melody Gardot. I just discovered her and new The Absence album. Very distinctive vocals and sound.
- Diana Krall. Lots of stuff. Some of my favorite songs are Temptation, Cry Me A River, The Look Of Love, So Nice.
- Norah Jones. I have Come Away With Me and Little Broken Hearts albums.
- Branford Marsalis. He is just awesome. Eternal is one of my favorite albums.
- Madeleine Peyroux. Very distinctive vocals. I love her early stuff, albums Dreamland and Careless Love in particular. When I first discovered her I was totaly smitten.
- Holly Cole. She has a lot of good stuff, songs like Too Darn Hot and Hum Drum Blues.
- Stan Getz. Samba sounds of the 60s. Tenor Sax at its best. Albums Getz For Lovers, Getz/Gilberto, Jazz Samba are some examples.
- Finally not jazz but I'll just toss in Regina Spektor and her new What We Saw From The Cheap Seats album. Man this girl has talent. Again, a very distinctive sound.
Finally there is a local Jazz station here in Toronto that you can listen too online at jazz.fm. It's heavily donor supported and has minimal commercials. I have been listening to it for years and donate quite often. This is the station that turned me on to Jazz several years ago.
For every expert, there is an equal and opposite expert.