No rap before Hamilton is under exposure to NYC boom bap.
Lin-Manuel Miranda is quite good but I am sure he wouldn't put himself on the level of Big Pun or Nas.
Miles Davis - Kind of Blue is the best selling jazz album of all time but it is still a specific sub genre of cool jazz that might put you to sleep.
Herbie Hancock - Head Hunters I think is the second best seller. I really don't know if I have ever read someone say Head Hunters sucks. It probably isn't what you expect in the same the way Hamilton sounded different to you.
I would go with those two and if you don't like either I wouldn't bother looking for more.
Not OP and not a jazz expert, just throwing out a personal favorite. I think it is very approachable without sacrificing anything, and it has a recognizable melody (which might help or hinder the jazz appreciation cause):
My Favorite Things by Coltrane.
But I do know people who dislike jazz because of the unfamiliar rhythms and (wildly flexible) musical conventions, and that can be hard to overcome.
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.
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!
