[taffronaut]

Most posts here seem to be offering easy on-ramp listening for jazz, but they seem at odds with the spirit of the original post. For jazz that is off-putting at first listening but rewards deeper study, consider Thelonious Monk (Blue Note sessions 1 & 2) or if you are really up for it, Coltrane's Interstellar Space.

[palata]

I think sometimes it's just a matter of finding an incentive. Isn't it typical for a teenager to start listening to the music of their boyfriend/girlfriend? Or of their group of friends.

My point is: I find that all the suggestions here are great! They may work differently for different people!