tl;dr start with either Europe ‘72 (great example of their live skills) if you want to start with a live recording or American Beauty/Workingman’s Dead if you want to start with studio stuff.

that’s a great question! i could spend several pages on this so i’ll keep it short haha. it is biased towards the 60’s/70’s since that’s the era I’m most familiar with and enjoy most.

Studio albums I recommend:

• American Beauty (Aug-Sep ‘70) – ⬅️ Start here for studio albums! this and the one below are maybe their two most popular releases and showcase their quintessential Americana country-rock-folk style. “Sugar Magnolia” would become a mainstay of theirs throughout their career.
• Workingman’s Dead (Feb ‘70)
• Anthem of the Sun (Sep ‘67-Mar ‘68) – actually a “hybrid” album as it’s an amalgamation of recorded live concerts and studio takes, this showcases their psychedelic rock period and demonstrates their improvisational skills. The suite “That’s It for the Other One” (later shortened to just the middle section as “The Other One”) would become a mainstay of their concerts as a launching point for jams
• Terrapin Station (Nov ‘76-May ‘77) – more into progressive rock now, a large chunk of this album would become live staples like “Estimated Prophet”, “Dancin’ in the Streets”, “Samson & Delilah”, and “Terrapin Station Part 1”
• Aoxomoxoa (Sep ‘68-Mar ‘69) – worth listening to for “China Cat Sunflower” which would become a mainstay of their live sets throughout their career
• Wake of the Flood (Aug ‘73) – snapshot of their jazz-rock era, contains more future set-list staples like “Eyes of the World”, “Stella Blue”, “Row Jimmy”, and “Let It Grow”
• From the Mars Hotel (Mar-Apr ‘74) – more jazz-rock, “U.S. Blues” and “Scarlet Begonias” are the two from here that would pop up most in future set lists
• Blues for Allah (Feb-May ‘75) – jazz-rock leaning more progressive, this was recorded in Bob Weir’s home studio. “Help on the Way” > “Slipknot!” > “Franklin’s Tower” would become a feature of many future concerts; “The Music Never Stops” is another standout from the album that would receive a lot of play in ‘76 and ‘77

Live albums I recommend: