36. Bob Dylan – The Freewheelin’ Bob Dylan

It’s interesting that, just like the last album I reviewed, this is not the debut of a legendary artist that made the list but its follow-up. In this case though, it makes sense. While I’ve always had a fondness for Bob’s eponymous first album, it’s charming not for Bob’s own stuff but for his takes on traditional classics like “In my time of Dying”. This one though, this was the start of something.

It’s impossible to define the early sixties music scene without Bob. In fact, scrub that, it’s impossible to define the early sixties without Bob Dylan. The sixties was a time when the barriers started coming down, where a new generation started getting angry at the world they were preparing to inherit, and this album was a soundtrack to it all.

It kicks off with the ever-familiar “Blowin’ in the Wind”, a song that is now such a part of our culture (we used to sing it in school assembly) that it’s hard to imagine it new and fresh. On this album though it fits nicely as a part of a trilogy of stunning folk, blending into “Girl from the North Country” and the no-holds-barred “Masters of War”. By the time they’re through the album has its hold on you, and lets you sink into “A Hard Rain’s Gonna Fall” and “Don’t think twice it’s Alright” (a song that gets me into that weird happy melancholy that’s eerily seductive).

As the album progresses into ‘Side 2’ as it were, the tone gets harder – “Oxford Town” is a lesson in tough political songwriting, but he manages to mix it with folk delights like “Corrina Corrina” and the tongue-in-cheek sign-off “I Shall be Free”.

Dylan had half a century of music ahead of him, and a career that almost defies compare, but this was a perfect little album that encapsulated all of his strengths – biting social commentary, love of Woody Guthrie era folk, heartfelt and brilliant love poetry and the ability to wink at himself.

Oh, and the cover? I always remember that bit in “Vanilla Sky” where Tom Cruise dreams himself into it as the epitome of intellectual cool. Who could blame him?