I like "Teatro" ...It's darn fine music!
I like "Willie and Family Live" and "Stardust" a lot. Interestingly, they were both originally recorded in 1978. I'm an admitted Willie fan, but I don't actually own much of his stuff (I should remedy that...). I do own the 3 disk "Revolutions of Time" collection and think it is fantastic!
Some of my favorite Willie songs are "Whiskey River, Stay a Little Longer, It's not Supposed to be That Way and Angel Flying too Close to the Ground". IMHO, all are best Live....
For old stuff, my favorite is Red Headed Stranger (1978) -- elegant in its own, very spare way; lyrical and moving. A great and pure Western album. For "newer" stuff, I think Across The Borderline (1993) has many terrific tunes on it, with covers of Hiatt, Lovett, Dylan, P Simon, Cooder included. The few or handful of duets on it are very nicely done. Don Was, producer, gets a really nice sound out of the sessions.
So much depends on which Willie you want to explore, because he is definitely a chameleon music wise.
I own a lot of his stuff and these are the ones that stand out for me:
1. Across the Borderline (1993). Willie doing covers. He is a gifted interpreter. His heartfelt best.
2. It Will Always Be (2004). Best singing and playing performance on an album in easily a dozen years. A songwriting workshop.
3. First Highwayman album (1985). Willie as the Outlaw with Johnny Cash, Waylon Jennings, and Kris Kristofferson.
If you like this genre of music, pick up a copy of Townes Van Zandt's
Texas Rain (2001). Great duet with Willie on "Maria."
See for yourself:
Townes Van Zandt
Oh man, I could go on and on. I am a huge Willie fan, and have quite a good chunk of his albums.
Two great early albums:
Phases and Stages; Shotgun Willie
These albums have many of his classics on them, along with many great songs many have never heard.
Stardust: This may have to be his prettiest album. The perfect album to turn the lights off too and sip your adult beverage of choice.
Willie and Family Live: This is probably the best party album from Willie. Many of the songs are done a little faster than the studio versions. It also gives you a peak of how great his live shows are.
Two recent albums: Songbird; It Always Will Be
I really enjoy both of these albums. Both are fairly raw with many tracks that have a nice bluesy feel.
Again, I love just about all of his work, but these albums will give a great look into what Willie has to offer.