Dusting ‘Em Off: Bob Dylan – The Freewheelin’ Bob Dylan


When an artist is able to deliver something that offers up solace, catharsis, and deep insight, it’s a remarkable achievement. But when a creative offering can maintain all of its emotional potency after half a century, then that’s a stroke of genius.

Today, The Freewheelin’ Bob Dylan celebrates its 50th anniversary. Even though The Crusty Curmudgeon Bob Dylan turned 50 back in ‘91 (making him 72 years young this past Friday), five decades of Freewheelin’ relevance provides the perfect occasion to revisit this folk-protest classic. The album touts some indisputable glimmers of brilliance, particularly when it comes to Dylan’s psychological phantasmagorias, budding sense of humor, and jabs at American militarism.

One fascinating facet to the LP is the subtle contrast between the album’s iconic cover photo and its title. For an LP called The Freewheelin’ Bob Dylan, our protagonist doesn’t come off as particularly carefree or nonchalant. In fact, if you look closely at the image it’s quite the contrary – he’s rigid, stiff, and encumbered by hefty emotional baggage.

A scrawny, baby-faced Bob Dylan treks down West 4th Street toward Jones astride his gorgeous girlfriend, Suze Rotolo.  Sandwiched between a low, grey winter sky and chalky, blackening slush, Dylan’s hands are thrust into the pockets of his blue jeans for warmth. Foolishly venturing out into the cold, gusty streets without hood or scarf, Dylan is compelled to shrug his shoulders and retract his neck into a thin tan jacket like some petrified tortoise with a mangy, unkempt Jew-fro. Rotolo, dressed more fashionably in a tailored forest green trench coat, black trousers, and shiny black boots, hangs on Dylan’s left arm, a step behind the folk troubadour, smiling electrically as she presses her cheek into Bob’s bony left shoulder.

Rotolo sure looks like she’s having a blast, but Dylan is another story altogether. His head is bent down toward the charcoal-stained snow, brow furrowed by concerns ranging from his precarious relationship with Rotolo to civil rights marches and the threat of nuclear holocaust. Squinting against a harsh wind, he’s practically dragging Rotolo down the street as she hangs on him like an excited little girl suffocating her giant stuffed turtle. So if Dylan’s not feeling loose and carefree, why’d he name the LP The Freewheelin’ Bob Dylan?

The album title’s indicative of Dylan’s promise to pull no punches. He’s beyond restraint, free of reproach, and prepared to slug it out with haymakers and uppercuts to the jaws of anyone and everyone. Quack psychoanalysts (“Bob Dylan’s Dream”), war hawks (“Masters of War”), and segregationists (“Oxford Town”) alike are all exposed to Dylan’s wrath. Even his girlfriend Rotolo, who ditched Bob at her mother’s behest to study in Italy for six months, gets subtly chewed out on seminal cut “Don’t Think Twice It’s Alright”. On 12-bar blues throwback “Down the Highway”, his animosity is far more blatant: “My baby took my heart from me / She packed it all up in a suitcase / Lord, she took it away to Italy, Italy!” Hell, Dylan even turns his critical eye inwards with self-depreciating humor on “I Shall Be Free”, adapted from Lead Belly’s “We Shall Be Free”, as he croaks: “Well, sometimes I might get drunk / Walk like a duck and smell like a skunk.” Might as well add “sing like a toad” while you’re at it, Bobby.

Freewheelin’ also marked the first time Dylan showcased his biting, salient humor that would emerge as a bedrock of countless subsequent offerings, from “Bob Dylan’s 115th Dream” off 1965’s Bringing it All Back Home to 1966’s Blonde on Blonde’s “Rainy Day Women #12 & 35” and “Leopard-Skin Pill-Box Hat”, all the way up to 2012’s Tempest. Take waggish, droll closing number “I Shall Be Free”, an instrumentally sparse ditty featuring Dylan’s anemic, jumbled vocal delivery and a torpid, downtrodden harmonica. Though dismissed by Dylan biographer Robert Shelton as a “decided anticlimax”, this cut nonetheless provides some of the best side splitting lines that Dylan’s ever written.

Joking around about the stagnant US economy and burgeoning Soviet muscle, Dylan describes a pestering JFK’s seemingly straightforward request: “My friend, Bob, what do we need to make the country grow?” Always the lewd prankster, Dylan’s deadpan reply is a trio of ’60’s sex symbols, one French, one Swedish, and one Italian: “Brigitte Bardot, Anita Ekberg, Sophia Loren / Country’ll grow.” Penned less than a year after Marilyn Monroe’s provocative “Happy Birthday Mr. President” hullabaloo, you’ve got to hand it to Dylan for shunning the predictable rhyming of “Monroe” with “grow” in favor of more exotic purveyors of American (erectile) growth. Or maybe American broads just didn’t do it for young Bobby?

Many of album’s most lasting and prophetic cuts are concerned with the American institution of war. Preaching in opposition to the engine of American militarism and its duel fuel injectors of manifest destiny and the industry complex, the quartet of “Masters of War”, “Blowin’ in the Wind”, “Talkin’ World War III Blues”, and “A Hard Rain’s A-Goanna Fall has Dylan approaching this thorny topic through oscillating lenses of realism, optimism, pessimism, and surrealism. Not too shabby for a 22-year old college dropout from Duluth, Minnesota.

Set to a stark, malevolent acoustic guitar, “Masters of War” takes dead aim at America’s military-industrial complex and the barons it enriches. Dylan, rather than focusing on the atrocities of any one massacre or campaign, takes a broader approach by exposing the mechanics and motivations underlying our obsession with warfare. Unsurprisingly, in the end it all comes down to the almighty dollar. Atop a brooding melody that borrows heavily from Appalachian dulcimer player Jean Ritchie’s arrangement of English riddle song “Nottamun Town”, Dylan pleads rhetorically: “Well let me ask you one question / Is your money that good? / Oh will it buy you forgiveness / Do you think that it could?”

Again employing a series of abstract rhetorical questions to denounce meaningless brutality and aggression, Dylan paints a somewhat less depressing picture on “Blowin’ in the Wind”. Pillaging slave spiritual “No More Auction Block” for a melody, Dylan yearns for a future where guns and bombs, not books and songs, are banished: “Yes, how many times must the cannon balls fly / Before they’re forever banned?”

Recounting a surreal dream from the vantage point of his psychiatrist’s couch, “Talkin’ World War III Blues” has Dylan singing of a fictitious landscape ravaged by war. Repelled at gunpoint when approaching a fallout shelter and shunned as a Communist for greeting a hot dog vendor with a hearty “howdy friend,” Dylan listens to a repetitive automated operator for over an hour to relieve his sharp pangs of lonesomeness. Needless to say, it’s not a pretty picture. But like so many superb folk ditties, the track ends on twin notes of commonality (“Well, now time passed and now it seems / Everybody’s having them dreams) and solidarity (“I’ll let you be in my dreams if I can be in yours”).

And then there’s “A Hard Rain’s A-Goanna Fall”, apocalyptically described by Dylan himself as being about “some sort of end that’s just gotta happen.” Lauded in The New York Times as “the promised fruit of the 1960s poetry-jazz fusion of Ginsberg, Ferlinghetti and Rexroth,” Dylan painfully sings of the end of days. Sharply contrasting a lithe, lovely melody with lyrics of “guns and sharp swords in the hands of young children” and “pellets of poison” floating in the sea, Dylan describes the horrors of war that he pessimistically conceives as inevitable.

(At the risk of getting real personal here for a minute, I can’t help but mention that “Don’t Think Twice, It’s Alright” has been the foundation for my entire ethos on failed relationships and painful breakups since freshman year of college. “I’m not sayin’ ya treated me unkind / You coulda done better, but I don’t mind.” To date, these lines speak volumes to me.

Reflect, but don’t dwell in the past. Passing judgment is one thing, but there’s no point in holding a grudge that’s never going to yield satisfaction or closure. These are very healthy sentiments to embrace if you’re a heartsick, privileged guy that feels like he’s been stabbed in the back by his best friend, closest confidant, and V-card swapper all at once.)

On “Don’t Think Twice, It’s Alright”, the cool, detached finger picking of session man Bruce Langhorne is set against a slow, deliberate melody lifted from Paul Claton’s “Who’s Goanna Buy You Ribbons (When I’m Gone)” that envelops the track in a disarming nostalgia. While filled with sadness and longing, Dylan contextualizes these feelings of dejection by establishing that getting dumped isn’t the worst thing that’s ever happened. It’s not the end of the world, and, more importantly, it’s nothing new. People have been getting hung out to dry since the dawn of civilization, so you’re in good company.

This sage wisdom is tremendously reassuring. Though the song’s lyrics are primarily directed at its female antagonist, Rotolo, they could be heard as words of wisdom, strength, and comfort for the song’s male protagonist and heartbroken young folk. (You  know, like my freshman self?) “Don’t think twice / It’s alright.” Wounds heal, we move on, and the molten rage slowly cools.  And in the end, it’s usually alright.

So happy 50th birthday to you, The Freewheelin’ Bob Dylan. While it’s hardly Dylan’s crowning achievement, it’s beyond repute that the LP was a major step forward for the singer-songwriter in his ascension to the “Voice of a Generation.” Hammering away at everything from the lunacy of American militarism to the intense burn of crumbling love affairs with potent lyricism, wry humor, and a deep understanding of Anglo-American folk traditions, Dylan at the tender age of 22 gave us a glimpse of the profound artistic insight he would channel and cultivate across his next five decades.