Earlier quoted context omitted.
I would have said no on Rap before Hamilton. I would like to know your goto for Jazz.
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.
My point is: I find that all the suggestions here are great! They may work differently for different people!