How to start listening to jazz

Intro

I know for many people, starting to listen to jazz is a difficult process. More often than not, people listen to the most advanced stuff possible and realised that they cannot keep up with it. This often results in problems of continuation. It's like starting to run again by sprinting. Everyone is going to feel fatigued and burnt out really quickly. If you try to listen beyond the level of your understanding, you would naturally feel overwhelmed and unable to cope with the magnitude of the amount of things you must juggle.

I personally believe the best way to do anything is to always take small steps. When you take the small steps each day, each week becomes a relatively bigger step; continue down this road and you'll be having leaps and jumps within months or years. Remember that music, or anything worth learning, cannot be learned within a day. If it was there would be no true reward.

Methods to learn to start listening to jazz, or any other music:

1. For most people who are just starting out, the usual problem with jazz music is that it just isn't "entertaining enough". If you keep listening to late John Coltrane, modern hardcore jazz, all the intricate stuff that is oh-so-hard to listen to, it will be likely that you are going to find more and more difficulty listening to jazz. These music do not explicitly indicate their form, structure, thoughts and message in a way which is very easily understood. As with everything (including metal and rock), you need to start with the easy stuff. There are plenty of great vocalists (since most music that everyone appreciates is vocal based) who can start you on understanding jazz as well, so you should start with the ones easier to appreciate.

2. There are several ways of understanding, analysing and feeling music. I personally like to talk about my method of listening to music. There can be many variations to it and many little details and orders can change, but I believe that by breaking down the music to understand it to begin with, you can tell what you like and what you don't like, and how to understand things that you don't like. The method of analysis/listening that I am talking about is on this post:
http://yourmusiceducation.blogspot.com/2010/05/how-do-you-start-analysing.html

3. Exchange music. I see a healthy exchange and tagging of Youtube videos on Facebook which is a good trend to begin with. But more importantly, exchange music in which you've analysed and think is good and you can actually bring it to others are share and see who likes what. Different people like different parts of jazz. But good music is good music. When you share and discuss, it helps a lot in consolidating your knowledge and understanding.

4. Listen to jazz exclusively for at least 1-3 months. What's the reason? Because in order to even begin to learn what jazz is, you need to immerse yourself in it. Many have tried to straddle multiple genres and learn it all at the same time, but mostly fail because when you don't even get the foundations of sound of each genre, you would not be able to truly understand and utilise it. It works for all genre. You must immerse yourself in it before you can truly understand it. There is no single person who hasn't immersed in a type of music and excelled in it before. Before the Indian musicians go professional, they have to spent 3 months to more than a year (depending on willingness) doing nothing but waking up and playing their instrument till night every single day. After that they can stop practising their instrument and still fly on it.

5. One of the biggest problems facing people is that they cannot muster up the will to want to go through the initial process - the inertia. Mostly because they say that they do not have the resources or external inspiration to really push on. Truth is, if you want to learn something, the only person who can help you is you. Finding resources and looking for friends who can help you are critical parts of learning.

I have a list of good crossovers for anyone starting out for jazz:

Vocalists
Stacey Kent (still insist that she's one of the best)
Diana Krall
Etta James (for those who love the blues)
Billie Holiday (a bit harder to touch base)
Ella Fitzgerald (usually great because she is both entertaining and artistic)
Lisa Ono (Bossa)
Esperanza Spalding
Laura Fygi
Pink Martini
Chaka Khan
Diane Shure

Instrumentals
Fourplay (great crossovers)
Casiopea
T Square
Oscar Peterson
Eric Marienthal
Chick Corea (especially for pianists and classical musicians) (early only though)
Duke Ellington Big Band
Count Basie Big Band
Django Reinhart
Wes Montgomery (he's like the beginning and end-all for all guitarist, just like how jimi hendrix is for all rock players)
Dave Weckl Band
Early Miles Davis (very good stuff)
Stan Getz
Grover Washington Jr
Jamiroquai (gets your funk on)
Even Red Hot Chilli Peppers (gets ya funk on too)
Art Tatum (great for classical pianists with exposure to ragtime and need a freaking fast player to inspire)
Hiromi Uehera
Larry Carlton
Alain Caron (great for bassists)
Level 42
Stanley Clarke
Marcus Miller
Wayman Tisdale
Chet Baker
Dave Brubeck
Dave Grusin
Bela Fleck and the Flecktones
Gordon Goodwind Big Band
GRP Big Band
Pat Metheny

The list is actually non-exhaustive though. If you find any musicians like Bill Evans or Dizzy Gillespie great to listen to, I'd encourage you to listen to them. Remember that these are great crossovers and for some are also great musicians all-round, but are more palatable for a whole host of reason.

Next level of listening

There is no such thing as a true next level of listening. There are people like Miles Davis in his times of electric jazz, and many fusion players who take it to the next level like Tribal Tech or Allan Holdsworth, but these are all dependent on one's taste and preference. The truth is that after you are able to analyse music on your own, you'd find the world of music a boundless place. =)

Conclusion

Hope this will help. It does take dedication and a lot of work. But if you just let yourself immerse yourself in jazz for 3-4 months, you can at least come out of it and realise that you have a strong FOUNDATION. And that is truly what you need. Though usually after the 3-4 months we actually go into more intensive listening more by choice than discipline now.

Hope this starts you thinking. =)