What an old thread to bump.. I really shoulda merged it with this one - bluelight.org/vb/threads/297557-Grateful-Dead-Appreciation-Thread back when I was still modding here
did that although that pretty much disperses the whole thread 6 years back into this one but oh well
I also would recommend skipping the studio albums.
Europe 72 I think would be the best introduction. My favorite live show (see above) remains 3/1/69 (very old and quite different from some of their later stuff), the cliché "greatest show" of course is 5/8/77 which also I think serves as a good introduction to that era. listen to and take in those three, I think, and you're off to the races to discover more of what you like in their incredibly vast repertoire.
I used to have an (old school kind with the black and white screen and wheel, but one of the ones with larger capacity, I forget tbh) iPod which was strictly Dead and had just about every good show from '69 to '95, a few hundred of them, but I lost it years ago (I used to bring it with me and some headphones everywhere when I was going to and from shows or partying or taking a bus or whatever, at some drug soaked event it just separated itself from me, I like to think that someone found it and appreciated it though) which was a great loss to me tbh, I can no longer instantly pull up some of my favorite shows, of which there are a bunch
the set of shows around halloween at Radio City Music Hall around halloween 1980 are a bit more obscure than most of this but are fucking amazing, a lot of acoustic stuff,
this is not a great recording (from 10/28/80) but a great tune,
this is set 1 (including weird ass prelude content including chilling a bit with (or more like trolling) jerry phil bobby & everyone else & some other weird shit from the official concert video recording) from halloween and set 2 should show up right next to it on Youtube…