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Sorry but that's an impossible question to answer. I have my favorite studio recordings and favorite live shows but even those are impossible to put in any kind of order. I love the early, bass-heavy bootlegs from 69-71 like some of the Hollywood Palladium and Fillmore West shows. '77 was the greatest touring year IMO and shows like Englishtown, Cornell, Rochester, etc. are all amazing. '74 Roosevelt Stadium - Help-Slipknot-Franklins is hard to beat from a recording standpoint, even on my old maxell. Whoever recorded that show did an amazing job capturing Phil at his best. JGB, Warner Theater, Washington, D.C. '78, late show - w/Maria Muldaur and others is one that's pretty special to me for a couple of reasons. I was there for one although I went to about 200+ shows so it can't be that alone. Maybe my favorite live Jerry solo of all time was during The Harder They Come from that night's late show. My good friend Bob was a DJ for the radio station (WHFS) that broadcasted the show and interviewed Garcia and he took the original soundboard tape from that set back to the studio and remixed it. I borrowed that tape from him about 10 years ago and it's still in my car. It's one of the most amazing recordings of Jerry I've ever heard. I think it was about 2am when he played that song.
As far as studio recordings, I don't think you can beat the early green label Warner pressings. I love the original W7 pressings of Anthem Of The Sun and Aoxomoxoa. If you haven't heard the originals, you should make a point to find a copy. They're pretty rare. Particularly Aoxomoxoa as they were pulled from the shelves early on and replaced with what eventually became the "final mix." I have 4 or 5 original copies of Aoxomoxoa and 2 or 3 of Anthem. In '80 or '81, Phil took Anthem Of The Sun back to the studio, remixed it and re-released it with a white cover. I have a nice copy of that one too and it's really, really good. Their first LP in mono is pretty cool too. It has the gold Warner label.
I could name 100 more but it's almost my bedtime.
How about you? What are some of your favorites?
'76 Klipschorns (Mahogany), '80 Cornwalls (Zebrawood), 1979 Cornwalls (Raw Birch) - Components Listed In System Profile