Sleepy Hollow Celebrates Bob Dylan...Through the Years
Bob Dylan | via The Guardian

Few, if any, artists of the past 75 years have led a career with the immense wealth of creative work as Bob Dylan. Born Robert Zimmerman in Duluth, MN on May 24, 1941, Dylan would begin to set popular music on a new course by the time he turned 22.

With his second album, 1963’s The Freewheelin’ Bob Dylan, he introduced his unparalleled craftsmanship of song in “Blowin’ in the Wind,” “Girl from the North Country,” “A Hard Rain’s A-Gonna Fall,” and “Don’t Think Twice, It’s All Right,” and became the country’s most popular folk singer and the adopted voice of his generation. When he released Bringing It All Back Home in 1965 though, Dylan had abandoned his post, alienating much of his audience by focusing less on overtly cultural and political topics in favor of a more personal, and of course, more electric approach to songwriting and performing.

This would be the first indication of a trend in Dylan’s career that saw him shifting from folk singer to rock and roll frontman (Highway 61 Revisited; 1965), country balladeer (Nashville Skyline; 1969), confessional singer/songwriter (Blood on the Tracks; 1975), Christian proclaimer (Slow Train Coming; 1979), and late-night crooner (Shadows in the Night; 2015), and that’s to name only a few of his personas…not to mention skip the ’80s, ’90s, and ’00s entirely.

And if not all of his recordings have managed to be consistently excellent (and many are), they have at least always been consistently intriguing. As we approach Bob Dylan’s 75th birthday this coming Tuesday (when we will celebrate with a full day of his music on #XPNDylanDay), the folks here at Sleepy Hollow give you a few of our favorite recordings from Bob Dylan’s vast catalogue.


“With God On Our Side” (The Times They Are A-Changin‘; 1964)

Dylan makes what many have said is his strongest social protest statement in this song. On “With God On Our Side,” he questions God and country in all its facets and turns the general premise of blind patriotism on its ear in poetic fashion and in ways that only Bob could. The song, performed by both Dylan and Joan Baez, became a touchstone in the disenchantment and distrust of the Cold War and later, Vietnam, by the counter-culture and others. It has worn well through the years, and is a prime example of Dylan’s early protest songwriting.

– Keith Kelleher

“It’s Alright, Ma (I’m Only Bleeding)” (Bringing It All Back Home; 1965)

If the snare hit that opens “Like a Rolling Stone” is the split second cosmic shift in sound that changed not only Bob Dylan’s career, but all of contemporary music in 1965, then “It’s Alright, Ma (I’m Only Bleeding)” is its long, slow build that indicated what was to come. In this writer’s opinion, it’s not only Bob Dylan’s finest 7 minutes and 29 seconds on record, its also one of the finest ever recorded by anyone. While so much was made of this album’s first side, which featured Dylan backed by an electric band, it is on Side 2 that he shows his true genius. Mired in fatigue, anger, frustration, and poignance, the lyrics read like a seething, sneering letter of intention to not only his peers and audience, but to the entire world-at-large. The irony of this era of Dylan’s music is that he would be criticized for abandoning the “topical” approach of his earlier recordings, but as “It’s Alright, Ma…” indicates, Dylan was still “topical” as ever, he was just now unwilling to approach his music or the world around him on anyone’s terms but his own. And in fact, this is likely Dylan at his most unabashedly radical, effectively tearing down in song that which he found unjust and corrupt, including, but not limited to, organized religion, the American government, and the hypocrisies and vanity of contemporary society. Indeed, Dylan’s lyrics are a hard pill to swallow, leading us down a grim path that, at least here, has no clear end or resolution, but as he points out in the songs final line, “It’s alright…it’s life, and life only.”

– Julian Booker

“You’re Gonna Make Me Lonesome When You Go”/”Buckets of Rain” (Blood on the Tracks; 1975)

Between 1966 and 1975, Bob Dylan released no less than four career-defining masterpieces (Blonde on Blonde, John Wesley Harding, Nashville Skyline, and New Morning), a stretch that saw him survive a violent motorcycle accident, help create a genre-defining style of country/folk/rock with The Band, and settle into family life with his then wife, Sara Lownds, and their five children (including Sara’s daughter, Maria, born of a previous marriage and adopted by Dylan). But by 1975, Dylan’s relationship with his wife had become estranged, a situation chronicled with tragic, startling clarity on his best album of the ’70s, Blood on the Tracks. With the exception of, perhaps, Joni Mitchell’s Blue, few songwriters have portrayed the heartbreak and emotional duress of a crumbling relationship as eloquently or honestly as Dylan, especially on the sprawling “Tangled Up in Blue,” “Idiot Wind,” “Lily, Rosemary and the Jack of Hearts,” and “Shelter from the Storm.” But tucked away beneath these dense selections are two of Dylan’s finest, albeit compact, compositions: “You’re Gonna Make Me Lonesome When You Go” and “Buckets of Rain.” Keith says of the former:

[It is] Dylan’s perfect, succinct and melancholic way to sew up a lost relationship in a terse, descending chord progression with tasteful and understated production that wields only Bob on guitar and a lonesome bass line. The lighthearted melody combined with the heavy lyricism makes for a memorable, if wistful, adieu. [An integral] part of the whole work Blood on the Tracks, it holds its own as a little gem of a tune when played outside it’s usual setting.

On the album’s final track, “Buckets of Rain,” Dylan manages to sum up the entire emotional spectrum of Blood on the Tracks in a mere 3 minutes and 23 seconds. And what is so striking is how much unbridled love and compassion there is in these lyrics–when Dylan sings, “Like your smile / And your fingertips / Like the way that you move your lips / I like the cool way you look at me / Everything about you is bringing me / misery,” he expresses how much care he still holds for the song’s subject, but openly addresses the fact that their relationship has failed. Full of regret, heartache, love and loss, “Buckets of Rain” stands among an elite group of Dylan’s album-closing tracks, a list that includes masterpieces “It’s All Over Now, Baby Blue,” “Sad Eyed Lady of the Lowlands,” and “Tonight, I’ll Be Staying Here with You.”

– Julian Booker

“Dark Eyes” (Empire Burlesque; Columbia; 1985)

There may not have been much to celebrate for fans of Bob Dylan in the 1980s (1986’s amazing box set Biograph notwithstanding), but 1985’s Empire Burlesque (which featured an excellent cast of musicians including Benmont Tench and Mike Campbell) is a brief ray of light, particularly in the spare, somber “Dark Eyes.” Sounding more like his most recent peak of the mid-’70s and less like, say, Saved or Shot of Love, “Dark Eyes” is as dire and complicated as anything in Dylan’s catalogue, and, if nothing else, proved that he still had the ability to write and record excellent, relevant music. It would be some twelve years before Dylan made an album this good, and had probably been ten years before that (save, perhaps, 1983’s Infidels). Regardless, Empire Burlesque and “Dark Eyes” merit revisiting, as does the excellent cover over the latter performed by Dawn Landes and Bonnie “Prince” Billy on 2014’s Bob Dylan in the ’80s: Volume One.

– Julian Booker

“Most Of The Time” (Oh Mercy; 1989)

Dylan ends the ’80s with a strong effort: Oh Mercy features the production of Daniel Lanois, who is a curious, but effective choice at getting out Dylan’s strengths through different and atmospheric means. “Most of the Time” shows a middle aged Dylan coming to grips with his weakness and doubt and questioning his own being. Lanois’ production brings out this struggle to a poignant peak and takes the listener on Dylan’s journey. Part of one of Dylan’s strongest efforts of any decade.

– Keith Kelleher

“Not Dark Yet” (Time Out Of Mind; 1997)

Hailed as Dylan’s comeback album recorded after a near death experience, Time Out of Mind marks the return of producer Daniel Lanois, a move that resulted in an atmospheric masterpiece that is as languid as it is ferocious. It is Dylan coming to terms with his own mortality, and features strong songwriting that has the listener’s ear from the opening track, “Love Sick” to the last piece, the sprawling 16+ minute “Highlands.” For this listener, “Not Dark Yet” ranks with his best, showing a brooding Dylan, with dreamy and ominous production behind him, painting a world-weary view that, though not shining a light at the end of the tunnel, makes it worth the trip with its eloquence and grace. 35 years of songwriting that started with optimism and change had fine tuned his rage into a feigned and dignified disconnect with the world. A towering achievement in songwriting.

– Keith Kelleher

“Moonlight” (Love and Theft; 2001)

In retrospect, we probably should have more clearly seen Bob Dylan’s preoccupation with Frank Sinatra upon hearing this track towards the back half of his excellent 2001 release, Love and Theft. But then again, like so much of the album, “Moonlight” is so much more than that. Received as well as, if not better than, 1997’s Time Out of Mind, Love and Theft proved finally that Dylan was again able to string together a serious of vital, remarkably consistent recordings (and that certainly did not stop with 2006’s Modern Times or 2009’s Together Through Life), and opened a surprisingly successful decade for him. On “Moonlight,” Dylan not only channels the Rat Pack croon that would soon become his vocal weapon of choice, but also the Countrypolitan sound of Patsy Cline, Chet Atkins and early Willie Nelson. What’s more, Dylan produced this album himself (crediting it to his pseudonym “Jack Frost”), allowing for a crystal clear reflection of his vision at the time, and resulting in arguably his best record of the 21st century.

“Autumn Leaves” (Shadows In The Night; 2015)

Six decades later and Bob Dylan wants to confound the critics and his listeners with a stab at the Great American Songbook covering Irving Berlin, Oscar Hammerstein & Cy Coleman among others. The common theme: many of these classics were covered by Ol’ Blue Eyes himself, Frank Sinatra. The result? A record of understated poignance with Bob at his contemporary best with outstanding production and accompaniment. It is Dylan giving his thanks to some of the songwriters and songs that he loved in his youth, and it shows the artist coming full circle with his beginnings. A worth-while diversion for true Dylan devotees, I had to go with one of my favorites since my childhood, the classic “Autumn Leaves.” How many artists have gone through six decades with so much quality, diversity and sincerity?

– Keith Kelleher

Selections from Chuck Eliot:

“Girl from the North Country” (The Freewheelin’ Bob Dylan; 1963)
“Mr. Tambourine Man” (Bringing It All Back Home; 1965)
“Desolation Row” (Highway 61 Revisited; 1965)
“Sad-Eyed Lady of the Lowlands” (Blonde on Blonde; 1966)
“If Dogs Run Free” (New Morning; 1970)
“If You See Her, Say Hello” (Blood on the Tracks; 1975)
“Beyond the Horizon” (Modern Times; 2006)

From all of us here at Sleepy Hollow, Happy 75th Birthday, Mr. Dylan!

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