Jazz Recommendations.

Print sources such as Down Beat or JazzTimes provide insight into the genre as well as copious reviews of current jazz releases. Both publications provide retrospectives of acknowledged jazz legends as well as links to other sites and radio stations. If the jazz neophyte's interest is piqued I would point them to books or articles written by Leonard Feather, Ira Gitler, Barry Kernfeld, Nat Hentoff and many others. As for music:

Mingus' "Ah, Um" is great fun, as is Sonny Rollins' "Way Out West"; but for pushing the envelope, try a dose of Perez Prado's "Havana 3 AM"

The more I think about it, turning on someone to jazz is more of a personal choice on the listener's part. It's like forcing someone to quit smoking, or going on a diet. Expanding your mind to something new is hard to do when you don't want to do it.

To turn someone on to jazz by getting them to start listening to jazz stations, reading books on jazz, cruising music stores to find jazz seems more work than most listeners want to do. Especially listeners that aren't into jazz in the first place. I got into jazz by getting into jazz. No one force fed it to me and I didn't find myself searching for musical truths. One day I picked up Kind of Blue because I heard so much about it and that was it. The flood gates were opened.

I am still trying to get into rap. Now, for me, that's a flood gate that's jammed and hard to push.

FYI:

I posted a thread about a Blue Note Records sale at Tower Records (25% off--no affiliation with tower) and included a list of Blue Note recordings that I think would be a welcome addition to any collection. It tends mostly towards Bop and Hard Bop, which is Blue Note's strength. Here's the thread

I would direct them to try some of the CD on this list: www.jazzwithbobparlocha.com/top40/

I agree with you, Matchstikman. Either one gets it (jazz) or not. Most casual listeners - those who have heard various cuts on the radio or in music stores - have no idea how varied the genre is. If there is no predisposition, no immediate emotional identification with the music, most people will not make an attempt to broaden their listening experience. For you, KOB opened the spigot and you began your foray into a unique world of music. For others, it might be Pat Metheny or Ornette Coleman or Von Freeman who opens the floodgates, but they are practitioners whose appeal isn't necessarily universal. I've introduced several people - who didn't care for jazz because they thought jazz was largely freestyle, 'formless' or something dated - by playing recordings by Davis, Getz, or Mingus, and then - if they show an interest - introducing them to the musicians so they might associate the music with pertinents such as socio/political conventions, cultural chronologies and personalities.
The publications and authors listed above go a long way toward providing a foundation to better understand not just the music but the motivations driving the performers. But you're right, if there is no open-minded, sincere interest in the genre no one can be 'converted' to jazz and all the good intentions won't change that.