When Leonard Cohen’s death was announced on November 10, the music world mourned its poet king. True, Bob Dylan has always been deified as the man who broke ground for all the singer/songwriters who followed in his wake, but even Dylan gave it up to Cohen, once telling the Canadian songsmith in no uncertain terms that he was “number one.” Looking back at Cohen’s half-century of communiqués from the soul, Dylan’s assessment is tough to dispute.

Cohen became an unlikely hero of the counterculture when his debut album, Songs of Leonard Cohen, was released in 1967. He was 33 at the time which, in the hippie heyday of the “don’t trust anyone over 30” ethos, was tantamount to having the words “irrelevant and unscrupulous” tattooed on one’s head. Not even close. Cohen already had success as a poet and novelist before entering the troubadour game, and at the time there was no precedent for transitioning between literary figure and underground musical icon. Nevertheless, he somehow transcended those barriers, and before his fellow Canadians Joni Mitchell and Neil Young had made their first solo statements, he was embraced as an avatar of the burgeoning singer/songwriter movement.

That first album presented an artist whose poetic powers were (at least) as potent as Dylan’s, but Leonard didn’t follow Bob’s Jackson Pollock-like approach of throwing colorful imagery at the canvas with brash abandon. Instead, the academically-trained Montreal native assembled richly symbolic, emotionally impactful lines with the careful mastery of an expert watchmaker. And his creations have continued ticking away for 50 years, earning a fresh crop of Cohen disciples among musicians and fans alike, generation through generation.

His voice was untrained but emotionally honest, a deep, soft moan that contained a wealth of sorrow and passion, yearning and regret, despair and resolve. The songs that voice delivered felt private and personal, yet utterly universal. The tender sentiments, small details, and religious imagery of “Suzanne,” the moody labyrinth of secrets and betrayals of “Master Song,” the absurdist humor of the tongue-in-cheek lament “One of Us Cannot Be Wrong”—they all slipped subtly but irrevocably into the ears of listeners who had finally found a singer to articulate their desires and dismays into something bewitchingly beautiful.

Cohen wasn’t afraid to plumb the darker regions of the human heart, and with his next couple of albums, Songs from a Room and Songs of Love and Hate, he became increasingly emboldened in his explorations of existential crisis, societal ills, and romantic malaise. From the wartime bleakness of “The Old Revolution” to the near-suicidal ideation of “Dress Rehearsal Rag,” he leapt into the poetic fray where few others dared to tread, earning a lifelong rep as the dark prince of the singer-songwriters.

But crucially, no matter how heavy things got, he always kept an ample supply of black humor close at hand. There are more laughs in Cohen’s canon than people realize—whether graveyard humor or outright farce. This is, after all, the man who would go on to write a riotous tune called “Don’t Go Home With Your Hard-On,” and cast wry aspersions on his own vocal abilities in “Tower of Song” by sarcastically declaring, “I was born with the gift of a golden voice.”

From the mid-‘70s to the mid-‘80s, Cohen went from strength to strength on the discs New Skin for the Old Ceremony, Recent Songs, and Various Positions, but his public profile slipped from darling of the underground to denizen of the fringes, supported solely by a small-but-hardy cult following—at least in America. Little did he know at the time that a song from 1985’s largely unheralded Various Positions would one day be a key to his immortality.

In 1988 Cohen made an unexpected comeback at the age of 54 with I’m Your Man. Largely abandoning his old acoustic guitar-based sound for sleek synthesizer arrangements adorned with a dash of irony, he played the role of greying roué, accentuating the subtle sex appeal his romantic utterances had always held, and amplifying the poetic richness of his writing. Arch tunes like “First We Take Manhattan” helped win him a new audience and wider renown. 1992’s The Future was a worthy sequel, offering a simultaneously withering and hopeful portrait of America that resonates to this day on “Democracy” and, on “Anthem,” presenting one of his most widely quoted, philosophically mighty lines: “There is a crack in everything/That’s how the light gets in.”

After a long layoff that found him, among other things, doing time at a Zen Buddhist monastery in the foothills of Los Angeles, Cohen returned to active duty with 2001’s Ten New Songs. In the intervening years, multiple cover versions of the Various Positions track “Hallelujah” (by Jeff Buckley, John Cale, and Rufus Wainwright) had turned the song into a modern standard, and American Idol finalist Jason Castro’s 2008 version would cement that status even further.

The song’s push helped Cohen become a bona fide star for the first time. He toured prestigious venues worldwide and sold them out on a regular basis. The albums he made in the last decade of his life were universally well-received. Even into his 80s, he seemed invigorated and revitalized, working with power and intention all the way to the end. His final album, You Want It Darker, was released just weeks before his passing. Invoking the Hebrew word for “here I am,” its title track featured the refrain “Hineni, hineni, I’m ready my Lord.” A fitting bit of closure.

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