Start with the simple and easy stuff: big band and orchestral, that's the 'pop music' of jazz.
Then go for the birth of cool: Miles Davis, John Coltrane, etc.
The trios and quartets serve a different purpose to big band. The bigger orchestras play off the sheets, but the smaller line-ups have infinitely more freedom to improvise and solo. They get to throw the rule book out the window and go their own way, which offers a rich selection of artists to choose from. As you begin to find your feet musically, you'll find that you're already discerning between what appeals to you and what doesn't.
The form of jazz music makes its own rules.
Here's probably the single most important record ever made.
Without it, the music of today wouldn't exist in the manner/form it does.
Miles Davis: 'Kind Of Blue' (1959)
Trumpet: Miles Davis
Saxophone: John Coltrane
Saxophone: Julian 'Cannonball' Adderley
Piano: Bill Evans
Bass: Paul Chambers
Drums: Jimmy Cobb
Additional piano: Wynton Kelly
What makes this record so important is that Miles was searching for a new sound. Something a bit more raw and to the bone than the up-tempo dance music of the big bands and orchestras. Davis stripped it all back to the very basics and started to rebuild musical form by taking its clothes off and presenting it as is. No sheets to read from, but a whole universe inside one's gut to propel the music forward while keeping it as minimal as possible.
Understatement rather than brash.
Introverted as opposed to extroverted.
Naked rather than a clown suit.
It was a very daring thing to do for the times it was made in and it forged a whole new direction in modern music that still reverberates today. Every newcomer to the jazz universe eventually reaches the point where it all comes down to this album. As a black man in America, Davis (and Coltrane) had to use the staff entrance even for sold-out shows in Radio City Music Hall and Carnegie Hall. It galled him. So this album was one way of stating his mind on modern America.
As ethereal and gentle as it sounds, the forces within it are atomic/nuclear - they ripped the art world a new arse.
One time, Miles attended a dinner at the White House. He was seated next to Nancy Reagan who asked who he was and what he does; and he replied:
'
I'm Miles Davis. I've changed the course of music five or six times in my lifetime. What have you done except fuck the president?
In many ways, I envy those who are coming to this album for the first time.
It may be subliminal, but it changed my life - umpteen times over.
It still does.