There is so much ground to cover! Indeed, the Grateful Dead were different bands at different times across their long history. Different both in terms of competency, health and style. If you have access to Amazon Prime, check out Martin Scorsese’s documentary “Long Strange Trip” to get an idea of just how screwed up the Dead were and how’s it’s a miracle they played so many great live shows.
Here’s my primer:
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For audio quality, as well as a time when the band was relatively clean and really on top of their game, nothing comes close to the Spring 1990 series. There were two sets of these shows released, all are fantastic. The 3/29/90 Nassau show, also release as “Wake Up To Find Out”, which features Branford Marsalis, is extra excellent. I only listen to so much Grateful Dead these days, and when I do, because of the superior sound quality, I turn to this run of shows.
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Acoustic Grateful Dead is excellent. In 2019 they released “The Warfield”, which features the opening sets from 2 nights in 1980, both acoustic. Playing and SQ are excellent. “Reckoning” is also very good.
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The late 70’s is another great period. The May 1977 “Get Shown The Light” features several shows from an iconic month. Including the famed 5/8/77 Barton Hall show, reputed by many to be the best show they ever did.
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I’m not that crazy about early Grateful Dead. Europe ‘72 is ok. And the official releases like American Beauty and Workingman’s Dead are excellent. But for me, it’s the late 70’s, 1980 - 81, and 1989-90. Brent Mydland came on in 1980, and he was, imho, their best keyboard player.
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For a showcase of Jerry Garcia at the height of his powers, check out “After Midnight”, the 1980 Keene College Jerry Garcia Band show.
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“Go To Nassau” is a fun show, an excellent Peggy-O and Althea. “Truckin’ Up To Buffalo” is also fun.
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Yes, it’s possible to find legal audience recordings of shows online. With extremely rare exception, the audio quality of these user taped shows is poor by audiophile standards. It’s best to stick with the official releases for SQ.