Jazz Recommendations.

If you wanted to turn someone on to Jazz,what would you say
are must have's?
What type of Jazz? It's a pretty diverse art form that spans almost a century. Big Band? Ragtime? Bebop? Hardbop? Free Jazz? Fusion? Etc.?

That aside, I'd add for anyone listening to jazz: Coletrane "Giant Steps".

More later.
The two CD set from Columbia/Legacy: "The Essential Dave Burbeck"
Personally, I wouldn't start off with the standeard recommendations like Miles Davis, Coltrane, etc. I would recommend some of the more assessible jazz from the 50's & 60s, by such artists as Bill Evans (piano) Oscar Peterson (piano), Stan Getz (sax), Ray Brown (bass v) Art Pepper (sax), Monty Alexander (piano), Ben Webster (sax), Jerry Mulligan (b. sax), Dave Brubeck (piano), and for some what latter (date wise, not style wise) Andrew Previn (piano), Houston Person (sax) and for jazz with a little flavor of swing, Scott Hamilton. Mostly they have their own trios or quartets, doing standards.
Assuming that you are meaning jazz in the more traditional vein--as opposed to 'smooth' jazz--this is a fun place to start, although some of the albums will require a more lenient ear if you're not so accustomed to jazz.

A couple others that get my vote:
Tomasz Stanko - Suspended Night
Wayne Horvitz - Sweeter than the Day
Achim Kaufmann - Double Exposure

I would recommend the following albums because they have enough melody and a blues feeling that a non-jazz person can relate to, but are still first rate classics: The Sidewinder by Lee Morgan. Midnight Blue by Kenny Burrell. Ballads by John Coltrane. Coop by Bob Cooper. They are all still in print and easy to obtain.
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.
if they like rock or pop go with les mccann and eddie harris-live in montreux.....dave brubeck-time out......bill evans trio-'65.....charles earland-black talk.
Newbee's list is right up my alley and would be a very good start to the classic Jazz set.Brubeck/Grusin imparticular. There's no telling what someone "gets" until they hear it for themselves of course. Ive been listening to the smooth jazz/ contemporary myself as well as the classic stuff. Right now I think Artie Traum's music is fantastic. Combining a mix of sounds from his upbringing in NYC..with undertones of Methany and Spyro Gyra.

Grusin's "Digital Duke" is very good also.
Charles Mingus-Black Saint and Sinner Lady, Thelonius Monk- Monk's Music, Duke Ellington-Far East Suite, Keith Jarrett, Koln Concert, Wayne Shorter- Speak No Evil, Andrew Hill- Point of Departure, Bill Evans-Waltz for Debbie, World Saxophone Quartet-Review, Heny Threadgill, Just the Facts and Pass the Bucket, Joe Lovano- From the Soul, Ben Allison-Ride the Nuclear Tiger.
Well, first of all send that someone to a good Jazz concert. Preferably in NY to
some nice Jazz club. Last time I visited a some friends in NJ, we all went out
to Village to a Jazz club. Both are usually not into Jazz, but they really enjoyed
the concert.

Otherwise, here are the records that go me started more than ten years ago:
John Coltrane "Love Supreme", Charlie Mingus "Mingus,
Mingus, Mingus", Duke Ellington "Money Jungle", and Count
Basie "April in Paris". Also, there were some basic Blue Note and
Verve samplers that I picked up at some store.

Also, I do not necessarily agree to get someone started with the softer side of
Jazz. Depending on his current taste in music, you could possibly bore
someone to tears ;-) The website recommended by Howard (Boa2) certainly
would be a good start.

Good luck,

You might try THIS THREAD for suggestions. I found it very helpful when I first started exploring jazz, particularly Sdcampbell's posts.

My suggestions for entry selections would be Miles Davis - Kind of Blue, Bill Evans - Waltz for Debby and Sonny Rollins - Tenor Madness.
I find that most of the suggestions given have a good degree of merit to them but fail to take into account some quite important facts that any potential new jazz listener and fan should be made aware of from the get go. To wit:

1) You will have a very hard time finding a halfway decent FULL TIME jazz radio station anywhere in the US - even in NYC (where I live). Hearing new music will therefore be a major challenge, so be prepared to buy quite a bit of music without hearing it first.

2) You will have a very hard time finding a halfway decent jazz section in any local record/CD store. Sure, there are plenty of online merchants with vast selections but if you're new to jazz and need help and advice, forget about getting any on the retail level.

3) You will often find youself quite alone with regards to your musical tastes. Kind of like an opera fan at a death metal concert. Friends who claim to be into jazz will really be listening to their old Steely Dan and Stones records. People will pay lip service to Duke and Basie and Satchmo and Lady Day and Prez but will know little about them or their music apart from "Take the A Train", "Hello Dolly" and "God Bless The Child". Basically the world of popular culture will slowly pass you by.

4) And finally, if you also happen to be an audiophile, you will have the additional hardship of suffering through endless discussions on the best "sounding" jazz recordings, regardless of the caliber of the musicans involved in the recording. Hence the worship of nonsense like "Jazz at the Pawnshop" and the latest female singer de jour who records with the microphone halfway down her throat.

I know I'm being a little harsh but I did leave out many of the good things about being a jazz fan. How about getting to buy countless reissues and box sets with previously unreleased material and alternate and incomplete takes, sometimes entire CDs worth of 30 second breakdown takes. Or listening to those crazed jazz DJs (that is, when you're lucky enough to find them) who can spend a good half hour talking about why take 5 of "Parker's Mood" is far superior to takes 4 and 2 and, of course, the incomplete takes 1, 3 and 6.
I echo most of the responses here already, including Ralphp's. His (presumably he) post raises a few points I would add.

Look around for jazz stations on line. I know that there is WBGO in Newark, NJ, and WMOT out of Tennessee; there's another full time one in the bay area. There's also WKCR in New York which features Phil Schaap. Though these stations tend to play a lot of more recent and local stuff (something jazz lovers can be really condescending toward), they do mix it up some. And it's free sampling when you're starting out. Also, you can catch sessions of the NPR jazz programming ("JazzSet", "Piano Jazz", "Live from Lincoln Center") on line as well. Great ways to get to know the music.

Because the radio outlets are fewer and farther between for us, you do need to be prepared to buy. Used shops, it goes without saying, are great. They also tend to be cheaper on brand new stuff, and tend only to carry the more mainline artists, good for getting one's feet wet.

As Goheelz suggested, notice the other artists backing the title artist. The greatest period of this music involved cats listenting while playing back up, and then turning it into their own thing.

As for particular titles, lately I cannot get enough of Ahamad Jamal's "Cross Country Tour." It's a two-disc set that features some of his greatest stuff, which, incidentally, proved a big inspriation for one Miles Dewey Davis. Also gotta push the following:

Rachelle Ferell, "First Instrument" - range AND control
Coltrane, "Blue Train" and of course, "Love Supreme"
Wes Montgomery, "Smokin at the Half Note"
Ellington, "Live at Newport 1956" - wanna hear a saxaphone start a riot?
Branford Marsalis, "Renaissance"

In any and all cases, good listening.
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.

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.
bill bruford "one of a kind"
Something Else: Cannonball Adderly
Blues Walkin or Lush Life : Lou Donaldson
Take Five: Dave Brubeck
Breezin: George Benson
Prayer Meeting: Jimmy Smith
Pangea or Arghartha,Kind of Blue: Miles Davis
Headhunter: Herbie Hancock