In one of the finest moments of sequencing on this set, the next song up is “Boots of Spanish Leather,” an outtake from the Freewheelin’ sessions with Tom Wilson (Dylan would eventually re-record it for The Times They Are A-Changin’ in 1964). The contrast between the rousing chorus of “Blowin’ in the Wind” and the stillness of “Boots” is jarring enough to bring out new aspects of each song, with “Boots” sounding even lonelier, even more despairing. Written during a trip to Italy as his relationship with Suze Rotolo appeared to be crumbling, it sounds intimate and unguarded, intensely private rather than public; he needs a quiet moment to himself in order to rouse an audience with his friends.
Though known in folk circles, Dylan was still struggling to find a larger audience and break through to the pop market. He signed with Columbia in late 1961, which is roughly where Act II begins. He recorded his self-titled debut with John Hammond producing, but it was not the breakout anyone expected. Here’s where you might want to place your bookmark and give that album another listen, just to get a feel for how this young man presented himself to the world; unexpectedly, Bob Dylan might work better as an addendum to this bulky novel than as a standalone release. Even Dylan considered it a failure, both commercially and creatively, and he was moving so fast that these traditional tunes and talking blues were old news by the time it was released.
His follow-up, The Freewheelin’ Bob Dylan, did not come easy. He worked through a series of aimless sessions over several months, finally piecemealing an album that wasn’t too dissimilar from his debut. At the last minute Columbia decided that “Talkin’ John Birch Society Paranoid Blues” was potentially libelous and removed it from the album. Dylan was irate, but it worked out in his favor, as it gave him a chance to quickly record several new songs and redo about half the album, including “Girl from the North Country” and “Masters of War”—two of his best compositions from the era. The new tracklist sharpened his Cold War fears while also introducing more intimate struggles, in particular his insecurities about Rotolo. The album toggles gracefully between the public and the private, each lending weight to the other, which contributes to its status as Dylan’s breakthrough as well as just one of the best folk albums ever made.
