I generally consider myself fairly open minded about music. I listen to stuff that hasn’t been popular in almost fifty years. I occasionally listen to an indie rocker or two. Hell, bring on a rapper and I’ll give ‘im a try.
But the one type of music I’ve never been able to get into is jazz. It’s not for lack of trying. Or maybe it is for lack of trying. I’ve never tried too hard. I look at the sheer depth and breadth of jazz and become overwhelmed. I back away and I run away, heading for the comfort of a Bob Seger song.
There’s so many shifting contours of winding music that it seems remarkably easy to get lost. Where do I start? How do I even pick the first damn thing to listen to? Trying to grab ahold of smoke seems like an easier endeavor. John Coltrane? Miles Davis? Billie Holiday? Charlie Parker? Which person do I choose? And then which songs? Or which albums for that matter. It seems like certain albums need to be listened to in their entirety. No picking or choosing with “Kind of Blue”. Whole thing, man.
I need a Virgil is what I need. I need a guide to help step my way through this strange new landscape. This is my way of asking for recommendations.
Dylan Charles
dylancharles.net 
sounds like you’re looking for jazz: the cliffs notes version.
i think you should just pick one or two dudes at random and get into their music. that way, you establish a baseline from which to judge other jazz. and if you like other types of jazz later, you can recalibrate your baseline and fine tune.
Pick something you like, just one song, and use it to seed Pandora.
If that’s too broad, take this suggestion from a random commenter enter “Quintette of the Hot Club of Paris” as the Pandora seed. Resist the urge to wear a hat. Feel free to write while listening.
Ooo, that’s a great idea! I can’t believe I never thought to use Pandora. I’ll give it a listen. Thanks!