I love Woody (and Arlo, last Thanksgiving I saw him do the 40th-anniversary Alice's Restaurant concert at Carnegie Hall)!
I do tend to think of Woody's work more as individual songs that in many cases I know a particular cover of better than his own version, so I don't think much in terms of his albums, although I have a few. Probably my favorite collection is something I found last year on itunes after looking for a CD for years -
Hard Travelin', the soundtrack from an 80s PBS documentary (I have an ancient videotape of the show). It's basically all other people (the usual suspects, Arlo, Holly Near, Pete Seeger, Judy Collins Ramblin' Jack Eliot, etc) except for the last song, which is a Woody/Arlo duet of This Land is Your Land. Arlo sings the chorus with Woody, then solos on the verses Woody didn't get to record for the library of congress, the ones that make you really see how the song used to be a leftist parody of God Bless America.