By the time he stood on the Lincoln Memorial steps on that pivotal day in American history, his songs had been covered by dozens of artists and his fame was global.
Then it really picked up speed as he plugged in his guitar for electric and electrifying rock (which alienated many folk fans) and his fame and influence just grew and grew. It was emotionally punishing, so - using a motorcycle accident in 1966 as a way out - he tried to retire to live a quieter life with his family.
His albums John Wesley Harding (67) and Nashville Skyline (69) offered downbeat folk-flavoured and country-style songs at the time the world was going techno-glow after the Beatles' Sgt Pepper's.
But people still scoured his lyrics for clues, Baez and others called him to rejoin the political movement and give it direction, and freaks kept turning up at his home in Woodstock.
So he released the myth-demolishing Self Portrait (70), which contained some excellent songs (Copper Kettle, Belle Isle) as well as ridiculous stuff such as his multi-track treatment of Paul Simon's The Boxer and MOR ballads.
As he said in the essay in the Biograph box set (85): "I wasn't going to be anybody's puppet and I figured this record would put an end to that."
Self Portrait, was not well received.
In his Rolling Stone review, Greil Marcus opened with "What is this shit?"
Received opinion would have you believe people hated this double album. But they didn't.
It went to No4 in the US and sold three million copies. In this country it was carried to parties and barbecues.
It was easy listening Dylan for people who wanted to zone out.
In my experience, there were a lot of them, and the album was far from the unmitigated disaster some might have you believe.
That Dylan's ongoing Bootleg Series now turns attention to that often derided period 1969-71 makes sense.
If any years - which included his understated New Morning album released four months after Self Portrait, and sessions with the Band which subsequently appeared as The Basement Tapes - deserve reconsideration it is these.
The double CD, Another Self Portrait, offers stripped-back versions of familiar Self Portrait/New Morning songs (most vast improvements by being more intimate), a dozen unreleased songs (gentle treatments of the traditional Pretty Saro and a piano-supported Spanish is a Loving Tongue among them), two excellent demos (Went to See the Gypsy, When I Paint My Masterpiece), the unreleased Working on a Guru with George Harrison, and a slow If Not For You with violin (which Harrison covered on his All Things Must Pass album).
Many of these songs, as with those on The Basement Tapes - be they original or traditional - appear to come from a time well before this, or even their own period.
In their elemental simplicity they reach into the tap roots of American music before they became commodified into Americana.
This is a revisionist collection for sure, but it's the better for that - there's an expanded edition which includes Dylan and the Band live at the Isle of Wight - and one of numerous quiet delights which possess an easy familiarity.
Oh, and Greil Marcus writes one of the liner essays. He likes this one.
Stars: 4.5/5
Bob Dylan, Another Self Portrait
Verdict: Sleight of hand and history repeats, but anew
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- TimeOut