CK Retro Review: The Freewheelin’ Bob Dylan by Bob Dylan

After an accomplished but relatively nondescript (and non-selling) debut that relied primarily on borrowed material, no one could have expected how stunning Bob Dylan’s second album would be. With assured and ambitious songwriting and rapidly improving performance skills all over the place, The Freewheelin’ Bob Dylan still stands as one of the landmarks of Bob’s career. Here is a song-by-song review.


13. “Bob Dylan’s Blues”- After the smirking introduction that insinuates that Tin Pan Alley is no longer located in America, the punch lines fall a little flat. Add in the fact that the verses come off more listlessly disjointed than winningly haphazard, and you can see why this is the runt of the litter.

12. “Down The Highway”- If there’s a problem with Freewheelin’, it’s that there’s a wide disparity between the album’s haves and have-nots. “Down The Highway” has a cool stop-and-start guitar pattern to distinguish it, but not much else, making it one of the mediocre numbers that aren’t in the same league as the classics.


11. “I Shall Be Free”- After some pretty heavy material elsewhere on the album, Dylan decided to go out on a lark with this carefree, joke-filled number. Some of the jokes are of the “I guess you had to be there” variety, but enough land to garner a few chuckles and to highlight Bob’s off-kilter sense of humor.

10. “Honey, Just Allow Me One More Chance”- Although he shares the writing credit with long-forgotten Texas blues singer Henry Thomas, Dylan pretty much conjures a unique creation full of whoops and hollers and reckless energy. What’s impressive about the song is how much of a racket Bob can raise with just his guitar, harmonica, and vocal.

9. “Bob Dylan’s Dream”- When Dylan talked about being “so much older then” in “My Back Pages,” he might as well have been referencing his character in this track. Although he was just 22 when this song came out on Freewheelin’, the wistful vocal and nostalgic look back through “half-damp” eyes at old friends now departed suggests a man four times that age. “Bob Dylan’s Dream” may be a tad too earnest, but it’s well-constructed.

8. “Talking World War Blues”- The talking blues would soon go the way of the dodo bird in the Dylan catalog, but this one is one of his finest in that genre. The satire of nuclear paranoia still holds up well even today when the issue isn’t as much on the front burner. That’s because Dylan plays it light, as his hapless title character comes to the realization that those people who worry about what it will be like after World War III are worrying about the wrong thing, since they probably won’t be around to see the aftermath anyway.

7. “Corrina, Corrina”- It’s notable for being the first full-band performance behind Bob Dylan on record, with Bruce Langhorne, who would go on to provide some memorable backing on future Dylan songs, providing the electric lead. It’s also a good example of Dylan’s imaginative renderings of folk material, as he gives this oft-sung lament a jaunty vibe that brings it into contemporary times. He also sings it with just the right amount of delicacy and restraint.


6. “Oxford Town”- An attempt to integrate the University of Mississippi which ended in an armed confrontation is the impetus of this understated protest song. Dylan simply lays the facts out here and lets the tragedy speak for itself. His simple, plainspoken rhymes also makes him seem like one of those affected by the violence rather than an outsider putting in his two cents. There may be more impressive lyrical feats on the album, but there isn’t anything that’s as direct a hit on its protest target as “Oxford Town.”


5. “Masters Of War”- Many people mishear the song as being anti-war, but it’s really war profiteers whom Dylan wishes would perish. This is as blunt as Dylan has ever been in a song, as he refuses to equivocate in any way and piles up the list of offenses that his enemies have accrued. If some of the techniques Bob uses here are manipulative, it’s the price he’s willing to pay for making his point. There is no doubting the raw power of his performance, one of the most mesmerizing he has ever given in the studio.

4. “Girl From The North Country”- One of the real revelations of The Freewheelin’ Bob Dylan is the tenderness that Dylan displays on the ballads. Taking the bare bones of the traditional “Scaraborough Fair” and expanding upon it, he movingly plays the role of a man wondering about the present exploits of his former love. The duet of the song Bob did with Johnny Cash on Nashville Skyline is charming, but it can’t match the intensity of the longing on the original. Another standout performance on an album full of them.

3. “Blowin’ In The Wind”- It’s a song so vast in its wisdom that it seems like it could have been bestowed on the world by a higher power, and yet it also seems that the truths held within it are so self-evident that any one of us could have written the song. Yet all of that mystical mumbo-jumbo denies credit to Bob Dylan, who stared all of this down at the tender age of 20 (which is how old he was when he first performed it in 1962, not when it finally arrived in his own version on Freewheelin’) and delivered the goods. It’s simply the quintessential folk song.

2. “A Hard Rain’s A-Gonna Fall”- Dylan’s famous comment in the liner notes to The Freewheelin’ Bob Dylan that each of the song’s lines could have been the beginning of a whole other song only sounds boastful until you hear them. By framing the song as a series of questions asked by a worried mother of her son, Bob raises the stakes, making all of the calamities the blue-eyed boy witnesses even more threatening. His protagonist’s promise to “know my song well before I start singing” is Dylan’s way of saying it takes vigilance and care to properly identify the obstacles in life one must overcome. One of the first Dylan epics, and still one of the best.

1. “Don’t Think Twice, It’s All Right”- Up until Dylan came along, there was little in the way of psychological reality to be found in the common pop love song. “Don’t Think Twice, It’s All Right” starts to change all that, as it meditates on the futility of love, the false starts and misconnections that eventually lead to the demise of a relationship. Dylan’s narrator seems alternately resigned to the end and frustrated at both the girl’s unreasonable expectations and his own inability to fulfill them. The emotion peaks when he bids her “fare thee well,” making it clear that, despite all of his protestations to the contrary, it’s not all right at all.

(E-mail me at or follow me on Twitter @JimBeviglia. For more on Dylan, my book Counting Down Bob Dylan: His 100 Finest Songs comes out in July, and the link is below for pre-orders.)


2 Comments on “CK Retro Review: The Freewheelin’ Bob Dylan by Bob Dylan”

  1. Baggy says:

    Good stuff CK, you’ve nailed the masterpieces and also the couple of weaker tracks.

    But you’ve been miserly with the three star awards. Talkin’ World War 3 Blues at least must get an extra star. The structure is masterly. And the appropriation of the Abraham Lincoln quote at the end is pure genius…i can’t imagine anyone else who’d have referenced it, changed it, made it funny, and used it as the get out line as Bob does here. It takes wit, balls, genius…that boy is a humorist with a list of references so vast… dammit, worth 2 extra stars for the ending alone.

    • countdownkid says:

      The talking blues are hard to rate as a whole for me. Without any melody or hook to build on, the lyrics have to carry all of the weight really, which means that have to be extra good. I do love the Abraham Lincoln quite and the “I said that” kicker at the end. Like I said, tough call.

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