I have only recently - in the past year - become a Chet Baker junkie (hmm, maybe a poor choice of words...oh well) but I have purchased at least 10 CDs and have a few recommendations. Of course a lot depends upon your musical perference as well because Baker recorded a lot of stuff in his career and it wasn't all one style.
My favorite stuff is from the infamous West Coast "phenom" period of
about 1950-56. This era began with the Gerry Mulligan quartet sessions
of 1952/53. The best compilation of these was probably the Mosaic boxed
set but that's no
longer available. So the best alternative in my opinion is:
* Gerry Mulligan - The Original Quartet with Chet Baker
Pacific Jazz (CDP 7243 4 94407 2 2)
This is a 2 CD set with liner notes by Ted Gioia and great vintage photos of the group
There is also a single CD compilation of these sessions called:
* The Best of the Gerry Mulligan Quartet with Chet Baker
Pacific Jazz (CDP 7 95481 2)
Its more of a "greatest hits" approach
Next I would recommend a nice CD of the stuff recorded by Chet's quartet with Russ Freeman after Baker and Gerry split up. This stuff was recorded in mid to late 1953:
* The Chet Baker Quartet with Russ Freeman
Pacific Jazz (CDP 7243 4 93164 2 3)
Following that I suggest a disc with several recordings of Baker when he was in Europe in 1955 (the trip when Dick Twardzik was found dead of an overdose just prior the the recording dates):
* Chet Baker in Paris - Volume 2
Emarcy 837475 - 2
And finally, in 1957 there was a reunion with Mulligan in New York. This work can be found on:
* Gerry Mulligan with Chet Baker - Reunion
EMI - Manhattan (CDP 7 46857 2)
This stuff isn't as good as the original Baker/Mulligan collaborations but is still solid.
Now, most of these feature a small group "cool" jazz setting, which is my musical preference. There are other, more hard-bop oriented recordings of Baker with Art Pepper, Stan Getz and and others, including an all-star session at the Lighthouse back in 1953. But I don't find Baker to be as creative in these endeavours. There are also recordings with strings, vocal recordings and work done in the '60's, '70's and '80's. While I have been told that some (but not much) of this later work is noteworthy, I feel that Baker's best work was done in the early and mid '50's and that his addictions consumed much of his talents later in life.
Just my opinion.