What happens when the voice of youth turns 80? Ask the enigmatic Bob Dylan.

·6 min read

There was a once a cartoon that chronicled the reluctant maturation of a generation. It ran in a regional newspaper, but was likely the production of national syndication. A rough recall of when it was published: 50 years ago this month.

The drawing depicted what was then a stereotypical post-1960s youth (collar length hair, John Lennon spectacles) thumbing through the album bins of a record store. Over his shoulder, was a hipster sales clerk giving unsolicited commentary on the artist whose works the customer was perusing.

“Better get them, now,” the clerk remarked. “All of Bob Dylan’s records are going to self-destruct when he turns 30.”

If a few slabs of vinyl would vanish in a puff of smoke once the generational figurehead hit the big 3-0, strap yourself in and look for mushroom clouds to bloom over what few record stores you can still find. On May 24, Dylan turns 80.

Such a milestone seemed unfathomable during those comparatively naive days of the ’60s and ’70s. Pop culture, including any ancestral variant of rock ‘n roll, was never viewed as an elders game. The music, along with the art it expressed, was a reflection of the times. More importantly, it was a declaration of youth. Singing the biting electric choruses of “Like a Rolling Stone” or “Positively 4th Street” at 60? 70? 80?. Get outta here, pops. You’re dreaming.

Remember Pete Townshend’s fabled verse from The Who’s 1965 hit “My Generation?” – “Hope I die before I get old.” Townshend, by the way, turns 76 next week and is still performing with The Who.

Of course, one of Dylan’s great talents through the years has been his ability to confound. Like any artist of lasting worth, his career ebbed and flowed with triumphs that reaffirmed his pop poet laureate/social wayfarer status of the ’60s and misfires that had critics and fans leaving him for dead more than once.

In this Dec. 8, 1975 file photo, Bob Dylan performed before a sold-out crowd in New York’s Madison Square Garden. Through constant re-invention, Dylan has remained relevant to music culture for seven decades.
In this Dec. 8, 1975 file photo, Bob Dylan performed before a sold-out crowd in New York’s Madison Square Garden. Through constant re-invention, Dylan has remained relevant to music culture for seven decades.

Yet, time and time again, Dylan has survived and thrived. He has released at least one landmark album in each of the last seven decades. Some built upon a deeply schooled folk voice from which all his electric aliases emerged. Others shifted producers and players and, subsequently, the focus of his songwriting. All were reflections of a writer who was as expertly versed in takes on societal graces and ruptures as he was on tales of personal turmoil.

The essential albums: There were a half-dozen classics from the ’60s alone - the folk-defining “Another Side of Bob Dylan” (1964), the electric manifesto “Highway 61 Revisited” (1965), the paisley poetic masterwork “Blonde on Blonde” (1966), the rootsy boomerang “John Wesley Harding” (1968) and the country detour “Nashville Skyline” (1969).

The ’70s gave us Dylan’s richest and most troubled romantic confessional, “Blood on the Tracks” (1974). The ’80s, Dylan’s most artistically erratic decade, closed with “Oh, Mercy” (1989), a brilliantly scorched meditation produced by Daniel Lanois, as was his finest ’90s recording, the ambiently inclined and lyrically prophetic “Time Out of Mind” (1997). The later triggered a considerable artistic renaissance for Dylan’s music that continues to this day.

The output slowed with the arrival of the 21st century, but not to the point where his records couldn’t balance a wary narrative glimpse of society with growing musical accents that echoed back to old world Americana. Submitted as evidence: “Modern Times” (2006), “Tempest” (2012) and the stylistic monsoon “Rough and Rowdy Ways” (2020).

What has made Dylan such a lasting and influential figure in popular culture? Well, his earliest career-defining music was born of a protest era fueled by the Civil Rights Movement and a fervent backlash against the escalating Vietnam War. But such ’60s-era unrest was at the heart of considerable popular music. Why has Dylan remained such an inspiration in the five-plus decades that have passed since then?

Many of the reasons, frankly, fall under the umbrella of mystique. Dylan regularly favored poetic observations of the world around him over plain-speaking commentary. Granted, there were songs like “Blowin’ in the Wind” and especially “The Times They are a-Changin’” that took on the ’60s head on. Similarly, Dylan was probably never more blunt than on 1975’s “Hurricane,” a blow-by-blow account of racially-charged events leading up to the arrest of prize fighter Ruben Carter for a 1966 murder.

But, for me, the best Dylan’s songs were never the obvious ones. Instead, what remained more fascinating through the ages have been tunes that relished in wordplay, that masked detail with the kind of poetic imagery that purposely opened the music to interpretation. Some of this work was rooted in beat poetry (but was never anchored by it), wrapping a sense of social unrest in a blanket of whimsy.

Offered for evidence: the social epic “Subterranean Homesick Blues” (“Get sick, get well, hang around an ink well; hang bail, hard to tell if anything’s gonna sell”), the more politically charged “It’s Alright Ma, I’m Only Bleeding” (“Temptation’s page flies out the door; you follow, find yourself at war; watch waterfalls of pity roar”) and the wonderfully obtuse “Stuck Inside of Mobile with the Memphis Blues Again” (“The preacher looked so baffled when I asked him why he dressed with twenty pounds of headlines stapled to his chest”).

These were all songs I remember discussing for hours with friends during college days, which fell a full decade after Dylan had written and recorded them. Successive generations, especially of musicians, have undoubtedly done the same. For them, however, comes the added thrill of addressing the wide stylistic breadth that has embraced Dylan’s songs from the ’70s onward – whether its was the gospel roar of “Saved,” the reggae/dub groove of “Jokerman” (arguably Dylan’s greatest ‘80s composition) or the meditative unease behind “Not Dark Yet.”.

If you don’t think today’s musicians still take Dylan seriously, then head over to The Burl next weekend. On May 23, a pack of regional pros (Ray Smith, Robby Cosenza, Jesse Wells, Tim Welch, Brad Slutskin, Roddy Puckett and Joshua Wright) performing under the band moniker of Seven Curses (a reference to an obscure early ’60s Dylan tune) will honor the songwriter’s 80th birthday with present-day readings of his very timeless music.

Of course, Dylan has been having a blast molding his mystique through the years to various whims, whether it was through the wildly revised arrangements he would lend to some of his most cherished songs in performance or brushing aside inflated critical estimations of his career.

The Dylan mystique was perhaps never put on more arresting display than during a December 2004 television interview for “60 Minutes.” Even in discussion with an expert journalist like Ed Bradley, Dylan was immovable. In one especially fascinating exchange, he all but dismissed Bradley’s considerable praise by replying with a question of minimal and unrevealing detail:

Bradley: “It’s ironic that the way people view you is just the polar opposite of the way you view yourself.”

Dylan: “Isn’t that something?”

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