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.