
When Warren Zevon appeared on David Letterman to “play his own wake”
David Letterman has shared more couched conversations with stars than a Californian therapist.
From an overtly sexual chat with Madonna to a nobnobbing with Tom Waits while George Clooney stood handcuffed behind him, Letterman, somehow, made a living from chatting, and to think that the people of his Indianapolis hometown used to build trains. But his candid conversations were always undercut by the comedian’s natural curiosity for life.
And there were few lives he was more curious about than Warren Zevon’s. The man Bob Dylan called the “musician’s musician” was not without his issues, and he often mulled over these in his music. They are staggering songs in both the drunken sense and the manner in which they might readily move a fellow maestro to tears.
So, in 2002, Letterman saw fit to ditch the multi-guest format and dedicate an entire show just to his friend. “It was the only time in my talk show history that I did anything like that,” Letterman told The Ringer, and he did so with good reason. Earlier in the year, Zevon had been diagnosed with terminal lung cancer, and it was acting fast in its progress.
Like most things in his life, this was merely something for the musicman to muse over, and he was more than open to being as candid as ever in the name of art. “I’ve never sat down and talked to anybody on television where we both understood they were about to die,” Letterman would reflect. Somehow, that didn’t stop the chat from being somewhat funny.

Zevon would even joke that this, his final public performance, was like “playing his own wake”. You might call this gallows humour if only he hadn’t been doing it his whole life, as he quipped shortly after, when asked about what the sudden illness had taught him: “You’re meant to enjoy every sandwich”.
His brutal diagnosis had given him three months to live, and he wanted to live it doing what he loved. So, aside from his heartfelt, oddly comic appearance on Letterman’s show, he also decided to make his final album, The Wind, which arrived hot on the heels of his previous releases when he was in good health, Life’ll Kill Ya and My Ride’s Here.
Once again, with the album, as with the talk show appearance, he was to some degree, “playing his own wake”. He expressed that he wanted these songs to be almost his last goodbye to his family and fans, which not only included Dylan and Letterman, but also the likes of Hunter S Thompson and Stephen King.
These final songs might have been recorded in a flurry, but he had hoped, akin to his TV presence, that they would give a truthful, lasting impression of his life and art. “I often wondered if he had been victimised by ‘Werewolves of London’, as that may have created an indelible impression of the man’s work,” Letterman told Vulture.
”While it’s delightful and humorous and funny and silly and good-natured and upbeat, it’s in no way even the tip of the iceberg,” he said of Zevon’s work. The Wind looked to go a little deeper, even if it did retain his lighthearted wit in the face of impending tragedy.
The last words he sang on that record, “Keep me in your heart for a while“, ring out in the wake of his absence.