I would have said no on Rap before Hamilton. I would like to know your goto for Jazz.

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.

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.

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.

Everyone is different of course, but if I had to try like this: do you know "Postmodern Jukebox"? :-)

Brad Mehldau for a great piano centric trio