Ranking the 5 Best Songs on ‘The Freewheelin’ Bob Dylan,’ the Birth of the Singer/Songwriter Era

Bob Dylan only wrote two of the 13 songs on his self-titled 1962 debut album. Just a year later, he jam-packed The Freewheelin’ Bob Dylan with 14 originals, several of which now stand as among the most momentous songs ever to come out of the canon of popular music.

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How did he do it? We’re still not sure. But we can go back through this incredible album to give to rank the five best songs therein.

5. “Girl From the North Country”

Dylan mostly stuck to topical material and rollicking comic diversions on the Freewheelin’ album. Love songs, or to be more accurate, love-lost songs, were kept to a minimum, perhaps because Dylan was already going against the grain. When he did approach them, he did so with the wisdom of experience that he couldn’t possibly have amassed yet (he was only 22 when the album arrived). “Girl From the North Country” keeps things simple lyrically, and the melody is age-old, but Dylan’s vocal conveys how bad it would hurt to have to give messages to your true love via a conduit.

4. “Masters of War”

A recurring theme here is going to be Dylan writing songs that are way beyond his years in terms of nuance and insight. Most other artists would have led with earnestness in an anti-war song. Dylan instead keeps his focus on locating the true enemy: those who would push war on the public so that they could profit from it. His protest songs were always built from the ground up with solid evidence, as if he were a prosecuting attorney, and he establishes that strategy expertly here. That allows him to make that brazen final statement about standing at the gravesides, because he’s earned that right by that time.

3. “Blowin’ in the Wind”

It’s hard to judge “Blowin’ in the Wind” fairly, if only because its influence was so monumental. Dylan wrote it around the same time as all the other masterpieces on The Freewheelin’ Bob Dylan, but it just so happened to get out into the world first. With everybody from The Beatles to Sam Cooke suddenly forced to react to this game-changer, Dylan went from nobody to phenomenon before anybody knew what happened. What’s interesting is this world-changing song is so gentle and non-committal, simply posing a series of questions to make its everlasting point.

2. “Don’t Think Twice, It’s All Right”

Dylan created something of a choose your own adventure song here. You can see his narrator as completely devastated, putting up a brave point as the girl he’s addressing drifts far from him. Or you can take him at his word when he tells her that her departure isn’t any big deal. There are lines you can pull from the lyrics to bolster your point, no matter what side you back. Based on Dylan’s woebegone vocal, we think he was leaning to the former interpretation. In any case, it’s a marvel of a performance, one where Dylan sounds so much older than the younger man he is now.

1. “A Hard Rain’s A-Gonna Fall”

While Dylan’s writing was leaving all his peers behind on this album, he was mostly relying on song forms that many others had used. But something like “A Hard Rain’s A-Gonna Fall” feels like a construct that hadn’t been done much within the bounds of pop music: the epic. Of course, there were multiple-versed folk songs throughout history, but none laden with such rich, striking language. Even within the song, he’s innovating, such as when he keeps building up the final verse well past its breaking point, which makes the moment when he heads back to the refrain hit with a walloping impact.

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