Heartbreak, hope and human imperfection: Leonard Cohen’s greatest songs, ranked!

A decade after his final album, and his death, we rate the best of the Canadian singer-songwriter who brought a deep, spiritual wisdom to love and grief

The synth-heavy production on 1988’s I’m Your Man has always been divisive, even Leonard Cohen’s longtime collaborator Anjani Thomas subsequently expressed misgivings, but on its opening track, it really works. The Pet Shop Boys-ish arrangement chafes against Cohen’s growling vocal, amplifying First We Take Manhattan’s shiver-inducing sense of brooding menace.

Seven years, and a personal financial crisis, after 2004’s half-hearted Dear Heather, Cohen returned to the studio with his powers freshly marshalled. As if to underline the point, Old Ideas opened with the sharply witty Going Home, on which Cohen’s muse addresses the listener directly, disparaging the artist himself as “a lazy bastard in a suit”.

Cohen famously called his 1977 LP Death of a Ladies’ Man “a catastrophe”, which perhaps reflected more on its drug- and booze-soaked recording with dangerously erratic producer Phil Spector than the finished album. It’s an outlier in Cohen’s catalogue, but one with much to commend it. Certainly, he maintained an understandable fondness for the rock’n’roll-influenced Memories, often performing it live.

Cohen’s renaissance continued apace on Popular Problems. Released the day before his 80th birthday, it sounded suspiciously like a masterpiece. Almost Like the Blues found him reflecting sorrowfully on man’s inhumanity to man, not merely torture, killing and war, but “all my bad reviews”, and staring down his own mortality, replete with a jab at Richard Dawkins.

Shruggingly titled, largely recorded in collaborator Sharon Robinson’s garage and packaged in a sleeve featuring a selfie, Ten New Songs was an understated return to recording after Cohen’s five years of Buddhist study. But beneath its unassuming veneer lurked beautiful songs: the chanson-like A Thousand Kisses Deep is an exquisite reflection on regret and time’s passing.

Nowhere else on this album does the cocktail of Cohen’s songwriting and Spector’s more-is-more approach to production gel so perfectly: the title track is a fantastic song. Moreover, the weight of Spector’s arrangement, the way it causes the tempo to drag, seems to complement rather than suffocate its mood.

Other artists have made albums that looked imminent death in the face, Warren Zevon’s The Wind, Queen’s Innuendo, but You Want It Darker, released less than three weeks before the end of Cohen’s life, may be the most poised and affecting. “I’m ready, my Lord,” he sang on its title track, a complex, thorny examination of faith.

In which a brief tryst with Janis Joplin, “We fell into each other’s arms through a process of elimination,” he later recalled, turns into a kind of eulogy, not just for the late singer, but for the era in which they met. It’s haunted by the sense of optimism extinguished.

Rock stars of a certain vintage were wont to write despairing state-of-the-world addresses in the late 80s, Lou Reed’s New York is full of them, but Everybody Knows is a cut above, its relentlessly bleak worldview leavened by black humour: “Everybody’s got this broken feeling, like their father or their dog just died.”

Against stiff competition, Songs of Love and Hate may be Cohen’s darkest album. Avalanche is its claustrophobic heart, a relentless, shimmering guitar figure, a confusing but compelling tumble of imagery, with his voice at its most poisonous. Nick Cave called it one of “the essential pillars that hold up the structure of my artistic world”.

Inspired by the story of the Lagerkapellen, concentration camp orchestras whose music accompanied forced labour and executions, there’s something eerie about Dance Me to the End of Love’s klezmer-inspired melody and lyrical pleas for lifelong fealty. The latter are filled with intimations of darkness; it’s never entirely clear that love will overcome them.

“I’ve seen the future, baby, and it’s murder”: Cohen’s apocalyptic response to the sociopolitical upheavals of the early 90s, most obviously the Los Angeles riots, depicted a world in which “attitudes are all extremist and they’re all defensive”. Thirty-four years on, it sounds grimly prophetic, its upbeat soft-rock backing only serving to amplify the unease.

Cohen found writing a trying experience, lurid stories abound of him beating his head against the floor while working on Hallelujah. He poured it all into the thrillingly vivid, mordantly funny Tower of Song, which has often struck a chord with other artists, covered by everyone from Phoebe Bridgers to Tom Jones to the Jesus and Mary Chain.

Anthem is home to perhaps Cohen’s most-quoted lyric: “There is a crack in everything, that’s how the light gets in.” But in truth, it’s just one among a plethora of memorable lines in the song’s gospel-infused paean to hope and human imperfection, a song he later suggested represented “everything my whole work and life had gathered around”.

Even by the standards of Cohen’s synth era, the backing of I’m Your Man is low-rent and cheesy, but it fits perfectly with a song about abasement. Its emotional tone shifts from lustful to desperate to hopeless: “A man never got a woman back, not by begging on his knees,” he notes in a moment of clarity, then carries on regardless.

Hallelujah’s progress from an album Cohen’s US record label refused to release to his most famous song, via, of all things, a cover by John Cale that appeared on the soundtrack of Shrek, is fascinating. Cohen later proposed a moratorium on its use in films, but, in truth, it has survived ubiquity with its power to move intact.

Cohen’s original intention was to try his luck as a Nashville songwriter. If you squint, you can just about make out the shape of a county song in So Long, Marianne’s beautiful admission of guilt, although it’s hard to imagine the Music Row treatment could improve on its wonderfully ramshackle string accompaniment.

Another Cohen classic with country music in its bones, Kris Kristofferson said he wanted the opening lines on his gravestone, Bird on the Wire was coaxed out of a depressed Cohen by his then girlfriend, Marianne Ihlen. It sounds utterly, authentically defeated, like one long sigh, destined to soundtrack moments of gloomy self-reflection for the rest of time.

There are infinitely worse ways to start your debut album than with a song so good, it immediately becomes a standard, covered by Nina Simone, Neil Diamond, Roberta Flack and Aretha Franklin. Some recompense, perhaps, for the titular lady’s refusal to let Cohen touch her perfect body with anything other than his mind.

Reducing Leonard Cohen’s oeuvre to 20 songs is a thankless task: the compiler is abundantly aware that umpteen deserving songs have been neglected. Similarly, there’s no head-and-shoulders “best” song, merely personal favouritism. Still, you listen to Famous Blue Raincoat’s disconsolate depiction of a love triangle, in the form of a letter to the other male party, and boggle at the idea Cohen was dissatisfied with such an impossibly beautiful song, which so perfectly conjures up an atmosphere of shadowy small-hours reflection, and which comes complete with one of his loveliest melodies (subsequently pinched on, crikey, Leo Sayer’s When I Need You).