How about Miles Davis 4 disc Live at the Blackhawk set?
Miles, Hank Mobley on tenor, Wynton Kelly on piano, Paul Chambers on bass, and Jimmy Cobb on drums live in a 1961 gig in San Francisco. Fabulous playing, with Miles more outgoing than usual, and not as well known as some of this later dates. Mobley is terrific too.
How much do you want to spend?
The cool looking japanese 24bit remasters that come in album-like cardboard sleeves are always cool. There are a lot of Coltrane titles to choose from. Love Supreme is one that all true jazz fans should have.
Get him one of the last Michael Brecker recordings (like "1 block from the edge"); very intelligent, mature compositions, arrangements.
Now that Michael is gone, all the more meaningful (how else to say it?)
I'm assuming that an avid Jazz fan would have many of the usual chestnuts from Miles, Coltrane, Ella, Sarah, Duke, Count, etc. Therefore, something somewhat obscure but great might be in order. I suggest "Thoughts of Dar Es Salaam" by the late LA pianist, Horace Tapscott. Horace was one of those unsung regional Jazz legends that deserved much wider recognition than he received. Horace was truly a musicians musician, one of those guys that everyone that visited the LA area were very eager to play with. "Thoughts..." is my favorite of his readily obtainable recordings and is always in heavy rotation. He was one of the great thinkers in the music, so there is always a lot going on, and many corners to explore. Pretty and challenging in equal measure.
A true avid jazz fan already has plenty Miles and Coltrane I would suspect. How about someting brand new and awesome? Drummer Paul Motian has released a bunch of brilliant things on ECM recently - Garden of Eden from last year with some great mingus tunes - and a new one just out this week with Bill Frisell and Joe Lovano "Time and Time Again" - to name just two. Check out the rave reviews on both - who says jazz has to look backwards? Let's keep it moving forwards - Motian is doing some brilliant stuff at age 75.
If you'd like to impress with your ability to find slightly more obscure stuff... try Chase Sanborn's "Cut to the Chase" or "Perking Up." The first CD is a compilation from his first two CDs, "Good to the Last Bop" and "Sweet and Low."
These also feature Guido Basso on horn and Carol McCartney on vocals.
"Jazz trumpeter and author Chase Sanborn is based in Toronto, Canada. Chase is a veteran session player who has performed with many top artists including Ray Charles, Aretha Franklin, Diana Krall, and for a brief but memorable engagement, a guy that juggles chain saws."
"A dedicated and celebrated educator, Chase Sanborn’s series of instructional books & DVD’s have garnered worldwide praise for their insightful yet light-hearted and humorous look at the world of music. Chase is currently a member of the Jazz Faculty at the University of Toronto, and travels frequently to appear as a Yamaha clinician and guest artist."
Disclaimer: Chase is my cousin. We don't do any kickbacks, though.
If you don't already know what your friend has in his collection, you might want to get a gift certificate. Squidco has pretty informative write ups on most titles, an excellent inventory and doesn't charge for shipping.
If you have a few days and you want to prolong the suspense try going to the mosaic record website and look there. They have 3 CD sets in a nice package,most of them contain the artists entire catalog. If I had to pick a few Andrew Hill is an absolute melodic genuis whose composistions in the 3 CD set dealt with the civil rights movement and the turmoil in the black communnity. the John Patton set chronicles his beginning and leads the listener to what Lou Donaldson and Lonnie Smith ended up recording Funky accesible jazz for FM airwaves. But if I had to pick one set it would be trombonist Granchan Moncur III which includes in my opinion the most over looked classic in the Blue Note catalog Evolution. I do believe they have gift certificates and if your friend has never heard of Mosiac then you have not only given him the gift of music but a website to get JAZZED up about.
a gift certificate.....as a collector, i hate to get albums or cd's(even rare stuff).....i want the moola to shop....thata at least half the thrill.
Try Manu Katche "Neighborhood". Pretty cool music.
Also, often overlooked Dexter Gordon is great on his tenor sax. His cd "One Flight Up" is really good and if he doesn't have it, I think it's a must have.
One Flight Up is a great recording and definitly a must have.
For Bebop,*Ray Brown-Live at Scullers,Don't Get Sassy,Summertime.*Oscar Peterson-Jazz Soul of Oscar Peterson,Jazz Portrait of Frank Sinatra,West Side Story.And perhaps best of all,*Gene Harris-Little Piece of Heaven,Black and Blue.Also *Junior Mance-Blue Mance.*George Cables Trio-Letter to Dexter.These are IMHO some of the best in the 'Bebop' category,of course there are many more.