The suggestion to get a guidebook on jazz recordings is the way to go. A book like the All Music Guide to Jazz not only lists most of the major artists and their recordings, it has a decent rating of each recording so you can sample the best.
The recommendation of the Ken Burns documentary series is also very good because it places the music in a social and historical context and employs narrators who know and love the subject and convey what the music means to them. The series is long but it is rewarding. The biggest problem for me was that the series stopped well short of covering what would have been at that time current jazz artists and their music; it was mostly ancient history then, and more so ancient history now.
If you want to hear a decent cross section of jazz development at a particular time, and appreciate how advanced jazz performance was quite a whiles back, sample the top recordings from just one year--1959. Three giant recording came out that year: Miles Davis "Kind of Blue," Dave Brubeck "Time Out" and Ornette Coleman "Shape of Jazz to Come." Of these three, my favorite is "Shape of Jazz to Come."