Review #255: The Freewheelin’ Bob Dylan, Bob Dylan

Karla Clifton
4 min readMar 26, 2022


#255: The Freewheelin’ Bob Dylan, Bob Dylan

We meet again, Bob Dylan.

My BD reviews haven’t been uniformly positive because … I don’t know that I have to explain more than that. I’m a twenty-seven-year-old girl in 2022. Forgive me for being resistant to someone who entered the music business over eighty years ago.

The RS blurb writes that good ol’ Bob was only 22 when Freewheelin’ was released in 1963, but fails to note that he sounds 1,000 years old. It’s his rasp, sure (remember, kids, smoking is BAD) but it’s also the sagely sentiments he’s communicating in his songs. “A Hard Rain’s A-Gonna Fall” makes him sound like a prophet who has been on every square inch of the planet six times over, and “Blowin’ In The Wind” manages to be both eternally young and eternally old. Life is hard, and some things are unknowable, yet you’ll never stop wondering away on the great truths that matter to your life. Also, Jenny sang “Blowin’” naked in Forrest Gump.

And even though I resisted the titles of “Bob Dylan’s Blues” and “Bob Dylan’s Dream,” there was something about both of them that just made him seem so … wise. Was it the suppressed rural/national pride, the stunted hopefulness? Enchanting nonetheless.

The woman with Dylan on the cover is Suze Rotolo, his girlfriend leading up to the release of this record. Sounds like she served as inspiration for a lot of his material, which is pretty clear from her presence on the cover and the two striking love songs. “Girl From the North Country” is so sweet it hurts when he sighs that she once was a true love of mine, and “Don’t Think Twice, It’s Alright” is heartbreaking if you’ve ever loved someone who didn’t return the favor. I gave her my heart but she wanted my soul, but he weakly asserts that she didn’t do anything but waste his precious time. Ouch, Bob. How come you had an affair with Joan Baez, if she meant that much to you?

Rotolo, who worked as an activist, played a big part in making Dylan’s music political and issue-driven as well. If there’s one thing I’ve learned in art school, it’s that people go bananas for issue-driven work. This record is the prototype for political indie. “Masters of War” is as badass as Bob Dylan gets (pre-Electric Dylan, obvi). It’s so dark that it’s kind of shocking. Jeez, he hopes that somebody dies! Surely that’s not true, Bob Dylan! You’re no Johnny Cash!

That’s not the only politically-motivated tune here, of course. “Oxford Town,” a catchy commentary about racism in academia, is more the protesty Dylan I’m familiar with. “Talkin’ World War III Blues” is a satire on war anxiety, and I kind of loved it — I love narratives about psychiatric hospitals where the staff are just as unstable as the patients. There’s something tongue-in-cheek about both of them that make them a little more fun than even his best anti-war tunes. (See “The Times They Are A-Changing” from his fourth album of the same name, which didn’t make RS’s list.)

The reason this album made me so happy was just that: the fun, the cheerful, the downright goofy. “Down the Highway” is a blast with some crazy fun guitar parts — I went running along the train tracks to this song and it felt kind of perfect. “Honey, Just Allow Me One More Chance” is one of the two covers here, and you can hear how much fun he’s having, using every vocal trick in his arsenal and putting on voices to give a brief, hilarious performance. “I Shall Be Free” has a deadpan delivery with some sharp lyrics describing the various idiosyncratic women in his life. Is Suze Rotolo the real humdinger?

I think Freewheelin’ proved to be my way into Dylan’s discography. Whatever Bob was searching to be able to say with this record is something I’ve felt before. I’ve been 22 and dramatic and had huge, massive feelings about war and love and peace and goofiness, but I can’t imagine being 22 and being able to put things like this into such simple words. That’s the reason this BD album is my favorite one yet.

Only Song I Didn’t Care For: “Corrina, Corrina,” the first of two covers. Boring.

Review #254: Head Hunters, Herbie Hancock

Review #256: Tracy Chapman, Tracy Chapman



Karla Clifton