As far as the mainstream is concerned, this is Bob Dylan's debut album. His actual debut, the previous year's self-titled record, is a mostly forgettable traditional folk record with only 2 original compositions (including the admittedly lovely "Song for Woody"). The Freewheelin' Bob Dylan signals that it is absolutely not fucking around by opening with arguably Dylan's most iconic song ever, "Blowin' In the Wind," which went on to be an anthem for the 1960s anti-war movement. When I was a kid, "Blowin' In the Wind" was one of those songs that everybody just knew, & if you didn't think about it too hard you wouldn't realize that it was actually written, like somebody sat down & wrote it on a piece of paper. It had become "Trad." I'm sure Dylan is elated by this outcome. Now it's transitioned into yet another stage. I don't think kids nowadays know "Blowin' In the Wind" or any other Bob Dylan song. They only know Dylan by the tendrils of his influence that still shape popular music today.
Dylan gets a lot of flak for his voice, but a close listen to Freewheelin' makes it clear that he landed on the best option available to him. He tries out a softer croon on the electrified, full-band "Corrina Corrina," & you can even hear a version of it in his gentle "Blowin' In the Wind" delivery. He does some cartoonish whooping on "Bob Dylan's Blues" & "Honey Just Allow Me One More Chance." The rest of the songs are delivered in the gritty nasal bluesman tone he'd use for most of the next decade.
People generally think of this album (& Dylan's acoustic period generally) as protest song-heavy, but he actually experiments with lots of different modes here. There are only 4 honest-to-goodness topical protest songs on the album. (There's also "A Hard Rain's a-Gonna Fall," which plants the seeds for the oblique poetic songs on sociopolitical topics that dominated Bringing It All Back Home & Highway 61 Revisited, though a lot of the symbolism is a bit too on-the-nose: "I saw a white man who walked a black dog.") There are a few traditional blues numbers, including humorous talking blues. The most out-of-place number, I think, is "Bob Dylan's Dream," where he yearns for the simplicity of his younger days with the maudlin sentimentality that only a prematurely fulsome 22-year-old can muster.
"I Shall Be Free" is a bizarre way to close the album. It's sometimes easy to forget that his album is the work of a 22-year-old after all, but this song--which seemingly exists only for Bob to talk about how much he likes to drink & the boners he has for various movie stars--reminds us. In fact, on this Dylan album more than any other, women are objects--either of desire, admiration, or humor. Consider that when the bomb goes off in "Talking World War III Blues," Dylan is saved from the blast thanks to being "down in the sewer with some little lover." The lover immediately disappears from the narrative & Dylan wanders around alone, although he later meets another woman whom he immediately invites to "go play Adam & Eve." The only exceptions to the marginal treatment of women here are the exquisite, pragmatic breakup song "Don't Think Twice, It's Alright," "Corrina Corrina" & the good-natured traditional adaptation "Honey Just Allow Me One More Chance." Dylan would spend the next few decades working through his troubles writing about women, but you can trace a lot of it back to this very album.
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