I'd have to vote for American Beauty and Workingman's. I really agree that nobody pulled off the 'americana' quite like the dead did, and I think they really inspired a 'movement' as it were in that era. I think bands with that country/folk/rock sound that sprung up around that time like, Poco or Nitty Gritty Dirt Band, really owed something to the boys.
Also it was a very transitional time personally for several of the members as well, and that really comes through in the songs. ie, Phil's dad was dying (BOR) and Jerry's mom died as well around that time. Beyond that the boys were becoming adults and all that that entails in your worldview (Brokedown, Attics). I believe that influences your music. At least it has for me. The last few years of my twenties and now into my early thirties has had a profound effect on my own compositions as well as the songs I want to cover. That's my opinion at any rate.
That said...let's talk about Tom Waits. He's one of the BEST songwriters of the 20th century hands down. If not the best. Heart Attack and Vine was the album that got me into him, the lead guitarist in a old band was a huge fan and turned us all onto him so we could cover the title track. We also used to cover Diamonds on my Windshield, from Heart of Saturday Night.
I think he's one of those where it's hard (impossible?) to pick a best or fave. Everything has been phenomenal. Granted, some more accesible than others. I'd list the following in my 'top' list:
Closing Time
Heart of Saturday Night
Blue Valentine
Heartattack and Vine
Frank's Wild Years
Nighthawks at the Diner
Raindogs (can any favorite album list not include this?!)
Bone Machine
Mule Variations
What are your opinions on these? I'd could chat for DAYS about any of them, esp. Closing Time. The trumpet melody line on the title track is soooo beautiful, I get goose bumps just thinking about it. And can you get anymore poignant than 'Martha' or 'I hope that I don't fall in love with you'? Who can't realate to those lyrics?
Also fave or top Dylan albums?
Peace.