It took me a long time to be able to appreciate jazz but nowadays it is by far my favorite genre, and I listen to anything from drone to trance, black metal to modern classical – just don't throw an average pop album my way, thank you. For several years I only had a couple of jazz albums in my collection and I can't remember if I ever got anything out of them back then. Then some years ago I devoted a lot of time and effort into acquiring more jazz records and trying to listen to them, trying to figure out what they were all about. I can't remember what inspired me to do this, but I'm truly glad for doing it. It probably took me close to a year of active listening to learn how to listen to jazz, what things to pay attention to and how to interpret what I'm hearing. Based on my own experiences, getting into jazz can take its time and it certainly takes active effort on one's part, but once you one day realize something has just clicked for you, it is a genre that will give back so much more than you had to give it, and then some.
Before I get to recommending you some stuff you can get started with, a quick word to dispel a misconception that some people getting into the genre, myself included, can have when they are first getting familiar with jazz. Some people have the impression that jazz along with classical is a genre you can only be able to appreciate if you have in-depth knowledge of music theory. Instead of trying to say in my own words how that simply is not true, I'm going to quote Art Blakey, one of my favorite jazz musicians and jazz drummers:
"You don’t have to be a musician to understand jazz. All you have to do is be able to feel. If you pass through life without hearing this music, you’ve missed a great deal."
Well said. All you really have to do when you listen to music, any music, is feel it. For me jazz – and just art in general – is first and foremost about expressing yourself, expressing your feelings and thoughts. That is why the improvisational aspect is integral to jazz for me. Since each solo is unique, you are expressing what you are thinking and feeling right at that moment, and because each performance is different, you have to always be constantly listening to what the other people in the group are playing and adapt your own playing to support what they are doing. This means there is always interplay going on between the members and therefore it is like everyone is having a conversation via music. There is of course music that is played on instruments typically associated with jazz, but with minimal or even no improvisation involved. This kind of music can certainly sound jazzy, but I have always found it difficult to decide whether I consider it to actually be jazz. Whether it is or isn't of course has no bearing on how good or bad the music is, but to me such music seems to lack the spirit of jazz.
But now to some music you can listen to. Below are some personal selections organized into a groups. Things that should be relatively easy to approach, slightly less straightforward stuff, and a couple of wild cards which with good fortune might resonate with you right away but might also likely require a bit more experience under your belt before coming back to them. I've also mentioned a couple of modern less traditional jazz albums which might strike a chord, you never know. Feel free to tell about your impressions and I'll be only happy to share more things based on your feedback. Also apologies in advance, I have no idea what is and isn't available on MOG, so if any of these albums mentioned are not on there that is simply unfortunate.
Also, why not check Rate Your Music's jazz chart on your own? Simply taking a look at the top 100 should keep you busy for a while. → Link ←
Simply essential basic albums
Art Blakey - Moanin'
Bill Evans - Waltz for Debby
Dave Brubeck - Time Out
Dexter Gordon - Go
Hank Mobley - Soul Station
John Coltrane - Blue Train
Miles Davis - Kind of Blue [The best-selling jazz record of all time. Need I say more?]
Oliver Nelson - The Blues and the Abstract Truth
Sonny Rollins - Saxophone Colossus
Thelonious Monk - Monk's Music
Once you've gotten your feet a little wet
Alice Coltrane - Ptah, the El Daoud [It is far too seldom that you get to hear harp in jazz like on this album's latter half. I also wouldn't mind there being more female jazz musicians in general.]
Art Blakey - Free for All [The title cut is simply a torrent of youthful energy.]
Charles Mingus - Blues & Roots
Charles Mingus - Mingus Ah Um [Pure brilliance from start to finish. Mingus was a genius.]
Dave Brubeck - At Carnegie Hall
Herbie Hancock - Maiden Voyage
Horace Silver - The Cape Verdean Blues
Jackie McLean - Destination Out!
John Coltrane - My Favorite Things [I think that the rendition of the title track on this album is one of the most important recordings in the still quite brief history of recorded music on our planet. It is simply an essential part of our musical heritage.]
John Coltrane - Crescent [One of my favorite John Coltrane records. This one often gets overlooked in his quite vast discography.]
Keith Jarrett - The Köln Concert [One of my personal top 10 albums of all time. I'm not religious, but this album simply sounds like god descended from heaven and played an hour for us.]
Mahavishnu Orchestra - The Inner Mounting Flame [One of THE classic fusion albums and something a fan of progressive rock might find it easy to get into.]
Miles Davis - A Tribute to Jack Johnson [Another fusion record a rock fan shouldn't necessarily have too much trouble getting into. I enjoyed this record long before the world of jazz opened to me.]
Pete La Roca - Basra
Wayne Shorter - Juju
More demanding must-hear albums
Eric Dolphy - Out to Lunch! [One of the greatest pieces of music ever recorded.]
John Coltrane - A Love Supreme
Miles Davis - Bitches Brew
Diana Krall - Live in Paris [You mentioned Diana Krall, but in case you haven't heard this one.]
Patricia Barber - Café Blue
Patricia Barber - Modern Cool
More modern jazz records
E.S.T. (Esbjörn Svensson Trio) - Viaticum
Hilary Hahn & Hauschka - Silfra [I'm not sure if this can be called strictly a jazz album, but it is completely improvised and blurs the line between classical and jazz. Also one of the best sounding albums I've heard in my life.]
Hiromi - Another Mind [Also search YouTube for videos of her performing live. It is seldom that you will find a person as joyous and full of life as this girl.]
Iiro Rantala - Lost Heroes [Only some sections contain improvisation, but an album well worth hearing. "Tears for Esbjörn" is dedicated to fellow jazz pianist Esbjörn Svensson who passed away and was Iiro's good friend. Iiro has said that he was depressed for a long time after his friend's passing and it had a large impact on his music.]
Iiro Rantala New Trio - Elmo [Just watch the video and you'll understand why this is not your typical jazz trio.]
Pekka Kuusisto & Iiro Rantala - Subterráneo
Portico Quartet - Isla
And there you have it. If that seems like a lot, trust me, it isn't really in the grand scheme of things.