"Another Self-Portrait (1969-1971)" is the 10th Bob Dylan Bootleg Series release. I've been a big fan of the series since it started way back in 1991, and this new Bootleg is one of the very best.
The original "Self Portrait" wasn't a high point in the Dylan oeuvre, but over the years I've come to take it on its own terms. Arriving just a few years after Dylan was at his creative zenith as a songwriter, "Self Portrait" was mostly a collection of old and obscure cover tunes, with a smattering of Dylan originals. They are decent tunes, but far from the standards he set with "Like A Rolling Stone," or "Blowin' In the Wind." Dylan fans weren't happy, but that was then; listening now to the stripped-down versions of these songs, you hear an artist searching for and discovering another side of his music. I should stop here and say "Another Self-Portrait" covers more ground than just that one album; it includes outtakes and never before released tunes from Dylan's "New Morning" and "Nashville Skyline" albums. I especially enjoyed the tracks with just Dylan, guitarist David Bromberg, and keyboard player Al Kooper working together, without any added production or instrumentation. The CDs have a very analog, very unprocessed sound, which will probably sound even better on the LP version. All of the tracks were sourced from the original analog tapes.
Many songs feature completely different arrangements than the ones we know. The loping, easy-rolling "If Dogs Run Free" transforms the original jazzy version, and the tune "New Morning" is radically different thanks to the big, brassy horn accompaniment. "Went To See The Gypsy" with just Dylan alone on electric piano takes on a confessional tone. I never heard "Belle Isle" before, but it's a traditional tune, arranged by Dylan, and sounds very much like a Dylan song.
The original "Self-Portrait" album had a few live tracks recorded with The Band at the 1969 Isle of Wight festival in England, and on the Deluxe "Another Self-Portrait" four CD box, you get the complete, 17 live song set. I wish "Wight" was being released separately, it's right up there with the best live Dylan albums. He actually sounds like he's enjoying himself, and he plays a mix of new tunes and "oldies" from just a few years earlier. Granted, the 1969 live recording's quality is uneven, but it's generally quite good.
Bootleg Series, Vol.5, "Bob Dylan: Live 1975" is another high point. Dylan assembled a huge band for the Rolling Thunder Revue tour, which I saw in NYC, and it was far and away the best Dylan concert I attended. The album captures the free-flowing feeling of the shows.
Don't miss Bootleg Series, Vol. 4, "Bob Dylan: Live 1966." Recorded in Manchester, England, you hear Dylan "going electric," and the audience was not happy. At that point he was primarily known as an acoustic folk singer, but Dylan wasn't the sort of artist who was that interested in giving the audience what it wanted. The two-disc collection has an acoustic set, but the electric set is, even now, shocking in its intensity. The character of Dylan's phrasing is incredible; he sounds like he's finally found his "voice."
Try a few Bootlegs; they all have greatness in them, and all 10 volumes are worthwhile. Dylan produced so much timeless music in his career, but if you're just now starting to discover his work, I'd hold off on the Bootlegs and go for either "Highway 61 Revisited," or "Blonde on Blonde." Dylan thinks "Blonde" is his best-sounding album, but I disagree; for me it's "Blood on the Tracks."