Trying to introduce someone to jazz?

I am an avid jazz enthusiast and admittedly younger than most people who are jazz fans. However, I think that it is really important to try to get more young people into jazz because I am honestly scared that it is pretty much going to die in America. I have a friend my age who is a big fan of music in general and who is a musician who has said "I like jazz i guess but I just haven't really gotten into it." And I understand. I think jazz is the type of thing you have to listen to for a little while before it finally clicks and you realize how amazing it is. Anyways, so I told said friend I'd make him some CDs. I don't want to give him too much all at once, so I've narrowed it down to the albums John Coltrane's "My Favorite Things" and "A Love Supreme"; "Kind of Blue," "Cookin'," "Steamin'," "Workin'," and "Relaxin'" By Miles Davis and his quintets; and "Jazz at Massey Hall 1953" with Diz, Bird, Bud, Roach, and Mingus, which is the recording that got me interested in jazz. But still haha I don't want to smother him, so I want to narrow it down even more. Any suggestions of one album I should give him? I'm thinking "Kind of Blue" or "Cookin'/Steamin'/Workin'/Relaxin' with the Miles Davis Quintet" (since those four pretty much go together anyways). What do you guys think?