The saddest songs in Leonard Cohen’s catalogue
Leonard Cohen is widely considered one of the greatest songwriters of all time, and for good reason. The deep-voiced Canadian started out as a novelist and poet before eventually putting his writings to music in the late 1960s. When he did so, he brought his previous vocation along with him, putting his lyrics at the centre of every song, infusing them with poetic weight and imagery.
There seemed no topic too dark or too dense for Cohen to delve into with his trusty pen. He wrote about his sexual and romantic relationships in excess, tackled his thoughts on God and religion, and pushed into his own feelings of regret and doubt. Many of these topics spawned songs that were intrinsically sorrowful, a feeling that was only intensified by his word choices and instrumentation.
He sets the scene with melancholic settings—New York in the cold, lonesome heroes smoking out on the open road—and then makes aching confessions of regret, longing, self-doubt, and self-hatred, each of them showing off his talent for conveying emotion through words. Beneath, he weaves together tapestries of strums and strings, soundscapes just as grand and just as devastating as the stories he tells.
Picking out the five saddest songs in Cohen’s catalogue is no easy feat. Almost every track has the potential to reduce its listener to tears, but there are some offerings that show off Cohen’s talent for melancholy more than others. From ‘Famous Blue Raincoat’ to ‘Dress Rehearsal Rag’, find our picks for the most sorrowful songs in Cohen’s catalogue below.
Leonard Cohen’s five saddest songs
‘Hey, That’s No Way to Say Goodbye’
Cohen starts out strong on ‘Hey, That’s No Way to Say Goodbye’. “I loved you in the morning,” he sings over warm twangs, “Our kisses deep and warm.” But he is a songwriter who can only fend off melancholy for so long. As the romantic first verse comes to an end, his lover’s eyes become soft with sorrow. “Hey, that’s no way to say goodbye,” he quips in response.
Cohen continues to drift between romance and sorrow throughout the rest of the song, finding both sweetness and sadness in their goodbye. He promises that their love will stay with one another, compares it to the shoreline and the sea, and states that “our steps will always rhyme,” making declarations that would usually be found in a love song written in the throes of early infatuation. But this is a goodbye, not a beginning.
‘Famous Blue Raincoat’
“It’s four in the morning,” Cohen begins, “The end of December.” Could there be a more melancholic setting? The songwriter returns to discussions of distance on ‘Famous Blue Raincoat’, comparing his cold life on Clinton Street to his lover’s new life in the heat of the desert. This time, his words are more bitter than tender. “You’re living for nothing now,” he sings, “I hope you’re keeping some kind of record.”
The instrumentation is more committed to misery, too. There are no hopeful twangs here, only desolate strums and deep vocal tones. “I guess that I miss you,” Cohen sings, “I guess I forgive you,” but his words are entirely detached. There’s another voice wavering high and low in the distance, too, perhaps from somewhere in the desert.
‘Bird on the Wire’
The melancholy in ‘Bird on the Wire’ stems not from romance or love but from a longing for freedom. The song is beautifully composed, with subtle cellos underlying each verse and strings that blossom with Cohen’s vocals. The strings alone could eke tears out of the most reluctant listener, but it’s the lyrics that cement ‘Bird on the Wire’ as one of the saddest songs in Cohen’s catalogue.
The songwriter reflects on his mistakes and misgivings, longing for forgiveness and freedom. “If I, if I have been unkind, I hope that you can just let it go by,” he begs, “If I, if I have been untrue, I hope you know it was never to you.” Every line is completely steeped in regret, driven home by Cohen’s poignant vocals. “I have tried in my way to be free,” he concludes, giving us no clues as to his success levels.
‘Dress Rehearsal Rag’
It’s four o’clock in the afternoon this time, but Cohen is still wallowing in melancholy. “I didn’t feel like very much,” he admits, “I said to myself, ‘Where are you golden boy, where is your famous golden touch?’” His lyrics are anxious, detailing trembling hands and cracked cups, culminating in a sad, shrugged, “Yes it’s come to this, and wasn’t it a long way down, ah wasn’t it a strange way down?”
At times, ‘Dress Rehearsal Rag’ features some of the most fervour instrumentation on this list, with strums that seem as agitated and self-conscious as Cohen’s words. Strings serve this energy, floating in the background to add a new sense of weightiness to the song. It’s perhaps the most hopeless and haunting song in Cohen’s discography.
‘A Bunch of Lonesome Heroes’
On ‘A Bunch of Lonesome Heroes’, Cohen laments the lost stories of soldiers. “‘I’d like to tell my story,’ said one of them so young and bold,” he sings, “‘I’d like to tell my story, before I turn into gold.’” There is a sense of second-hand longing for their stories to be told in full, rather than romanticised and turned into gold, but Cohen makes this seem like a pipe dream.
“But no one could really hear him,” he laments, “The night so dark and thick and green, well I guess that these heroes must always live there, where you and I have only been.” The song contains that characteristic sense of longing that seems to pervade all of Cohen’s writings, but it’s a longing for another whose story will never be told as he has told his own.
