Since falling in love with The Greatest, I've found it difficult to really enjoy her earlier albums. It seemed to me that they were more avenues for her own catharsis than adequate representations of her talent. The focus-being completely independent the first two albums, and on a rather small label up until her newest release-did not seem to be primarily on the music: her lyricism was good-at times astounding-but her musicianship was only moderately interesting and her voice did not sound like it does today. Although there are a few gems in her back catalogue that truly shine, most of the songs are too raw, hard, or unpolished to create a pleasant listening experience (they seem to work on some level in the background, or if you're really down, but they're difficult to love). The nature of her (past) music makes sense, considering her battles with alcoholism and depression. Here's a relatively recent NY Times article and video in which she explains some personal things.
After taking a couple years off from music after her 1996 album What Would the Community Think, she released a collection of covers she'd played on the road between 1998 and 1999. It's very interesting how much different the sound of this record is from her prior releases, and even You Are Free, which came out three years later. Perhaps the main difference is that there is no evidence of any other musicians: it's only Chan. She mostly plays her guitar, sometimes the piano, which allows her gentle, smokey voice to be heard as it should without detracting from its almost unnverving intimacy. She covers The Rolling Stones (I don't know if I've ever heard a more radically satisfying cover of a song than her version of "(I Can't Get No) Satisfaction"), Lou Reed, her (ex?) boyfriend Bill Callahan of Smog, and even herself, transforming each song into something nobody else ever could. The most similar song on The Greatest would have to be "Where is My Love," but somehow the songs on this album each have a weighty significance, like she inspected each of them with her heart and expects us to (i.e. knows we will) do the same. Chan's "Wild is the Wind" is perhaps the most hauntingly poignant, soul-piercing song I've ever heard. I absolutely love this album. It is a supremely satisfying listen straight through, and is best suited for listening at night, with quiet stillness, disturbed only by Chan's hauntingly beautiful voice.
Look for a song in my upcoming mix.