Jazz Recs for Classical Music Fan - Challenging

Having acquired 1000s of classical CDs (probably more than I could ever listen to), I think that it is time to start with some Jazz. I know there are a lot of forums, websites, and books that give much great advice on how to approach the subject. However, I am looking for more particular recommendations. Perhaps some fellow posters with classical tastes in the Romantic and Modern eras could give some recs that would nicely bridge the gap. I've tried to make my way into Jazz a couple of times, but haven't been successful to date. Perhaps someone here can help me make the breakthrough.

Here are some of the things I am looking for:
1) Decent recordings. This probably means something from the 60s, forward. A little tape hiss is OK, but excessively remastered or noisy recordings are not what I'm looking for. I know that many of the great recordings are from the 30s through the 50s, and I have ordered a couple of those.
2) Naturally recorded. No amplification, no over-miking, good engineering. Vocals should be minimally or not amplified. Soundstage needs to be realistic. The venue should be apparent. No 50 ft clarinets and vocals eminating from the entire soundstage.
3) Acoustic instruments. I do not like electronic music.
4) No divas-come-lately. I don't care to hear the latest 22 year old with a big voice, amplified and electronically filtered to 'perfection', a pretty album cover, and a marketing campaign to tell me how great she is.
5) Emotional content. Not just for tapping your foot or for background music.
6) Great performances. Not just something that came out last month with high recommendations in the press.
7) Probably smaller ensemble pieces. Vocals, piano, quartets, etc.
8) There may be some labels that have classical and jazz recordings that overlap (?ECM).

Miles Davis - "Kind of Blue"
Bill Evans Trio - "Waltz For Debbie", "Sunday at the Village Vanguard", "Moonbeams", "New Jazz Conceptions"
Coleman Hawkins -"Nighthawk"
Sonny Rollins - "Saxophone Colossus", "Way Out West"
Dave Brubeck - "Time Out"
Gary Burton/Chick Corea - "Crystal Silence"
Art Pepper - "Meets The Rhythm Section"
Ella Fitzgerald - "Clap Hands Here Comes Charlie"

There are so many great ones out there, but the ones I've listed above meet your criteria as well as being very accessible musically.
I second the Bill Evans. No pretty album covers with him on them.

Lee Konitz & the Axis String Quartet "Play French Impressionist Music from the 20th Century" Palmetto PM-2064, a gap bridger for you. A veteran saxophonist with help from some classical guys.

Carla Bley "Fancy Chamber Music"

Charles Lloyd's stuff on ECM. Some of it is a bit strange but some of it is mesmerizing. Try "All my Relations" or "Canto" on ECM or "Acoustic Masters I" on Atlantic.
Dave Grusin - Homage to the Duke (very well recorded, one of my favorite albums)

Dave Brubeck - The Essential (this is a 2003 two disc set put out by Columbia with 31 of his better recordings.)
If you are looking for some of the more adventurous and challenging jazz look at the Hat and Leo labels, they also overlap into the chamber modern classical vein from time to time. They both usually have excellent natural recordings without much gimmickry done to them. They are a little hard to find but worth seeking out.

From the look of your system you've got some good times ahead of you.
Rob, I've been making this same journey of exploration over the past year, moving from an almost exclusive base in classical music (as in more than 3000 LPs) to trying to understand and appreciate jazz. What worked for me was to focus on the "straight ahead" jazz ("hard bob"?) with a few artists I at least had some affinity for, and then branching out from there.

I started with the following recordings which meet all of your criteria and overlap with some other recommendations already given. (FWIW, I concur with Slipknot's list as a good set of recordings; they meet the requirements you laid out.) The following list simple reflects my path to learning to enjoy jazz comming from a purely classical music frame of reference...

Louis Armstrong and Ella Fitzgerald: "Ella and Louis" Verve 4003

Louis Armstrong: "Satchmo Plays King Oliver" Audio Fidelity ST-91058

Ella Fitzgerald: "Clap Hands, Here Comes Charlie!" Verve V6-4053

Billie Holliday: "Songs for Distingue Lovers" Verve 2015

Count Basie: "88 Basie Street" Pablo 2310-901 (this is a larger ensemble, but give it a try as an introduction to that genre. It's excellent.)

Miles Davis: "Kind of Blue" Columbia CS 8163

John Coltrane and Johnny Hartman: "John Coltrane and Johnny Hartman" Impulse GR-157

Sonny Rollins: "Saxophone Colossus" Prestige P-7079

Cannonball Adderley: "Know What I Mean?" Riverside 9433

Coleman Hawkins: "Coleman Hawkins and his Confreres" Verve MG VS-6110

Bill Evans: "Know What I Mean?" or "Waltz for Debbie"

Bill Berry: "Shortcake"

My collection of jazz has now grown beyond these, but I would again start my personal journey here if I were doing it again.
BeBo & Cigala - "Llagrimas Negras"
One of my dear friends who lives in Israel plays professionally classical piano and had been granted a very large gift from God.
She's very skeptic listening to jazz except when it comes to Chick Corea no matter whether it's acoustic or electric band.

ECM label is mainly oriented on neo-jazz and neo-classical directions so it might be very interesting to research for classsical music listener:
Terje Ripdal(Vitous DeJonette), David Darling, Pat Metheny, Charlie Mariano, Jasper Van't Hoff etc...
European jazz masters such as Jan Akkerman with Focus also had previousely studied spanish classical guitar had an influence of the middle-age serenades in his compositions.
Check out also Pekka Pohjola.
So far, so good. Keep the recs flowing. I have some on order, and I'll strike at BMG has another $2.99 sale.

I am definitely not opposed to modern jazz, and remain open to pieces that are not immediately accessible. I've been willing to experiment with modern classical music, and it can sometimes be rewarding. I just don't want something that is totally abstract or 'off the wall'.

Rob It's me who's totally abstract or even 'off the wall' sunk onto the underground staff but the list I gave you isn't abstact and has lots in common with classical music.
Unfortunally you less likely will get these at BMG for $2.99 sale...
I know BMG won't have much of this stuff, but I continue to be surprised at what they do carry. I've already found about 10 of the recommendations on their website so far. They even have contracts with smaller classical labels such as ECM, Hyperion, BIS, etc.
Miles Davis - In A Silent Way
Keith Jarrett - Koln Concert
Weather Report - various
Harold Budd - The Room (not really classified as Jazz)
A few more:
Charles Lloyd, "The Water is Wide" (small group)
Marcus Roberts, "Alone with Three Giants" (piano)
Joe Henderson, "Lush Life: The Music of Billy Strayhorn (small group) and "So Near, So Far: Musings for Miles" (small group)


Jim Crane
I'm a big fan of romatic era classical music ... Brahms, Schumann, some Beethoven etc etc.
My favourite jazz disc is "Our man in Paris" by Dexter Gordon (tenor sax) on the Blue Note label.
The recording is very natural, dating from the 60s.
There is some magical tenor sax playing.
I can't believe that nobody's mentioned Jacques Loussier yet. Try "Plays Bach" and "Baroque Favourites". These are jazz trio interpretations.
Try some esbjorn svensson. great piano trio ...do a google check for bio as well as some excerpts.also try bbc3..jazz
.there are many soundclips from all different types of jazz.
keep an open mind.
Maasada 8: Live in Sevilla. Great music, astounding musicianship, excellent recording.
A good place to start is with the classic records from the '60s. Small jazz combos playing bop, and hard-bop. Tons to recommend here.

Rather than providing another immense list, I would like to urge you to take very seriously the lists provided by both slipknot1 and rushton. These are very good suggestions and, in my opinion, are much, much better places to start than what many of the others have suggested. You will have plenty to work with there.

For what it is worth, you can get a great collection of '60s classic jazz from bmg. Look for the remastered versions of the classic blue note 60's stuff. All Music Guide (available on-line) can help you identify which they are. (Miles Davis, Grant Green, Freddie Hubbard, Eric Dolphy, Kenny Dorham, Art Blakey, Herbie Hancock!!, Johnny Griffin, Hank Mobley, Joe Henderson, etc., etc.)

Hope this is of some help.
There's a huge rich vein of great stuff out there that punches holes in the old category boundries. You're right to suspect that ECM is a good place to start, (Eberhard Weber "The Following Morning" or "Endless Days" are a couple of my favorites). You might try Louis Sclavis "Les Violences de Rameau" and Kenny Wheeler "Deer Wan"... there are dozens of other ECM releases that are equally good. The "Group Therapy" disc by the Jim McNeely Tentet (Omnitone) really seems fresh and alive, (you get a very nice interpretation of a Coltrane and a Bud Powell composition on this one). One recording that came to mind right away while reading your post was Beirach/Hubner/Mraz "Round About Monteverdi", the title (i know cor-ny) probably doesn't grab you, but the recording quality and the playing here will. Here are a few other possibilities:

Kamikaze Ground Crew/Senic Route

Franz Koglmann/L'Heure Bleue (this one is on Hat, Ejlif is right as usual)

Univers Zero/The Hard Quest (More ominous chamber music than what most people think of as jazz)

Tom Varner/Long Night Big Day

Wayne Horvitz/Sweeter Than The Day

Nils Wogram/Speed Life

Volapuk/Volapuk (Twisted Hungarian folk dance energy...maybe like if Bartok had an instrumental rock band w/ only cello drums and clarinet).

Giorgio Gaslini/Masks

Jerry Granelli/Another Place
I read you criteria. Because jazz started roughly at the time of commercial sound reproduction,some of the recordings sound like,well,remasters of recordings up to a century old.

Early Jazz--any of the compilation anthologies of Louis Armstrong,Hot Five/Hot Seven recordings. The music justifies the recordings' qualities.

Swing--Art Tatum. Since you said small ensembles,I'll pass on Basie and Ellington.

Bop--Charles Parker,Ornathology

Cool--Miles Davis/Gill Evans,The Birth of the Cool....Kind of Blue

Hard Bop.--Mingus,Ah Um. Coltrane,Giant Steps. Blakey,Night in Tunisia

Modern--Bill Evans,Sunday Afternoon at the Vanguard

As a classics listener,The Modern Jazz Quartet may interest you. They were together as an ensemble for decades and got so good that some thought they were playing written out compositions.

Enjoy the collecting
The Smithsonian put out a 5 CD, 6 hour set called "The Smithsonian Collection of Jazz" that covers 50 years or so of jazz, pretty much everything from Jelly Roll Morton through Ornette Coleman. Try that and see if there is anything you like. If not, you might try the 2 main forms of music, Country and Western.
Well, BMG now has their $2.99 sale. I just placed an order for 9 CDs that are recommended in this thread. I also bought 4 CDs from recommendations on a previous thread. After S&H, it came out to less than $7 per CD and earned me 2 free CDs. Pretty good deal.

Anything by Bill Evans, especially, Sunday at the Village Vanguard and Waltz for Debby.
As someone who listened to classical before discovering jazz, I've brought with me a preference for jazz that emphasizes composition. I like improv, but for my taste too much jazz glorifies the improv solo at the expense of the overall composition and structure of the song, and the results are often a bore of tag-team soloing. (I'm not a bop fan.) I prefer it when the solos are woven into the structure of the piece. I also want my jazz to swing and be fun. The mind working with the head bobbing. With that in mind, I would recommend the following:

Louis Armstong, who to me epitomizes the heart and soul of jazz

Benny Goodman, I particularly like his small trio and sextets. There's a lot more big band that is underestimated as good jazz.

Gerry Mulligan Quartet

Dave Brubeck

Count Basie

Duke Ellington

Miles Davis

Horace Silver

Oscar Peterson

Bill Evan also would fit here, but he's not my cup of tea for other reasons.

And a very different kettle of fish, but Pat Matheny. I can't stomach all of his work, but at his best he can craft a terrific composition

Vocals also tend to ground jazz into some overall stucture, though some jazz vocals can be too light on the jazz.

If anyone else has suggestions along these lines that I haven't mentioned please pass them on.
Look thru the Concord Jazz catalog. They have a lot of small groups playing jazz mostly from the 70's forward. Excellent artists, if not some of the best know. The recordings are usually outstanding.