Jazz Recommendations.

I think Boa2's list would scare most neophyte jazz listeners away. Although I love the albums listed I don't agree it's a good start. Too out there for the most part.

If your friend is coming from pop/rock , e.s.t. would bridge the gap rather well.

The best answer to the question is... Mr. Miles Dewey Davis III on trumpet, pre-1968. The other good answers join Mr. Davis on various of these recordings.

Dave Grusin - Tribute to Duke & Two for the Road.

Great production values, excellent musicianship, and timeless tunes.

I would choose something from Miles Davis to start them off. If they come from an easy listening type of background, I might have them start with Kind of Blue. You can't miss there. If they come from a rock and roll kind of background, I might start them off with Miles Davis live at the Fillmore, March 7, 1970. This rocks, for sure. Another choice might be Bill Evans, Portrait in Jazz, or perhaps something from John Coltrane, Blue Train.