Thanks a lot just looked up the real book and wow.... it has about 450 pages and thats just volume one haha .The first album I suggest for my students who know nothing about jazz is "Moanin' " by Art Blakey and the Jazz Messengers. Also, Clifford Brown's "Study in Brown" makes jazz accessible as well as understandable.
As far as songs go, there are as many different opinions on what songs to learn as there are jazz drummers. You can pick yourself up a copy of "The Real Book" and start checking them off when you know the tunes. That's a good reference, and it will take you a while to put a dent in that tome.
Other than that, just listen to as much jazz as you can...immerse yourself in the genre. That's how you pick it up and it starts making sense. Good luck!
+1Get Kinda Blue - Miles Davis.
More than many other categories of music, for jazz, it is Imperative that you do a ton
Read your local entertainment papers/ads/sites, find local live jazz - and go watch and listen.
Kind Of Blue is a great entry point into jazz. Lots of people find the modal style less difficult to gain an appreciation for. It's jazz of the highest order with fine musicianship all around and great compositions.
Jimmy Cobb is a real artist on the kit. He plays a minimalist style on KOB but he gives a great example of how a jazz drummer can play time and swing the band without filling up space unnecessarily. He changes sound colors behind the soloists and uses dynamics to great effect to bring some drama and excitement. You won't find any drum solos here, just a master of swing and understatement at work.
I've always described Jimmy Cobb's approach on KOB as "pocket" jazz drumming. It's a wonderful starting place especially for drummers familier with the concept of supporting or playing for the song.