Leonard Cohen released his last album, You Want It Darker, just three weeks ago.
With lyrics like "I'm leaving the table / I'm out of the game," the 82-year-old singer-songwriter and poet was facing his own mortality.
And he told the New Yorker: "I am ready to die. I hope it's not too uncomfortable. That's about it for me."
His son, Adam Cohen, said his father died "with the knowledge that he had completed what he felt was one of his greatest records".
Cohen will be remembered as one of the world's best-loved singer-songwriters.
But he once said that he got into music because he could not make a living as a poet.
Cohen was born in Westmount, Montreal, Canada on September 21 1934.
Born to a Jewish family, he later considered himself both a Jew and a Buddhist.
He formed a country music group called the Buckskin Boys while still in his teens, saying that "guitars impress girls".
He published his own book of poetry, Let Us Compare Mythologies, to critical acclaim, in 1956, while still at university.
It was followed by The Spice-Box of Earth in 1961, when he was 27.
After a stay in London he moved to the Greek island of Hydra and published his first novel, The Favourite Game, in 1963.
He lived there with Marianne Ihlen, and wrote her the song So Long Marianne. Her death earlier this year inspired his final album.
After moving to New York, Cohen decided to embark on a career as a songwriter and musician.
He released his first album, Songs Of Leonard Cohen, in 1968 and travelled the folk circuit with younger artists like Bob Dylan, Joni Mitchell and Joan Baez.
His most famous song, Hallelujah, has been covered by hundreds of artists and is now a staple in movies, TV shows and YouTube videos.
As he aged and his voice got deeper, Cohen remained hugely popular into his 80s, touring as recently as earlier this year and singing on the Pyramid stage at Glastonbury in 2008.
The Suzanne and Bird On A Wire singer was also inducted into the Rock and Roll Hall of Fame in 2008, saying: "This is a very unlikely occasion for me. It is not a distinction that I coveted or even dared dream about."
Cohen suffered bouts of depression throughout his life that he sometimes tried to mitigate with alcohol and drugs.
Once asked if he was a pessimist, he responded: "I don't consider myself a pessimist at all. I think of a pessimist as someone who is waiting for it to rain. And I feel completely soaked to the skin."
Cohen will also be remembered as a poet, novelist and aspiring Zen monk.
For part of the 1990s he lived as a disciple of Zen Buddhist monk Joshu Sasaki Roshi at the Mount Baldy Zen Centre in Los Angeles.
"I was the cook up there," he said. "My life was filled with great disorder, with chaos, and I achieved a little discipline there. So I decided to return to music."
Cohen had two children, Adam and Lorca, with artist Suzanne Elrod.