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.
.
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.
.