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Author David Rakoff was born in Montreal, went to high school in Toronto and was a New Yorker thereafter.Frank Gunn/The Canadian Press

In his final completed book of essays, Half Empty, David Rakoff wrote about what he called "the power of negative thinking" – the idea that preparing for the worst is more a practical lifestyle choice than a character defect. Still, even Rakoff's most catastrophe-minded readers couldn't have prepared for the news that he passed away Thursday from sarcoma.

The Toronto-bred writer made an appearance on Public Radio International's This American Life live show only three months ago, and he didn't look well – his story, about how cancer had taken away the use of his left arm, was a poignant and sad reminder of how bad his illness had become. But still, it seemed inconceivable that a writer so present and so rigorous could be taken at age 47. He will yet be remembered as one of the best American humourists of his generation (even if he was born here).

Like all great humourists, though, Rakoff was a tonic for his cultural moment, a gleeful puncturer of American delusions, and he was having too much fun to ever be truly despairing. As American comedy continues its descent into silliness, Rakoff was one of the best pointed pessimists left.

Rakoff was only ostensibly Canadian. Born in Montreal, he graduated from Forest Hill Collegiate Institute in Toronto, but then left for Columbia University in 1986 and never left New York, physically or in terms of his outlook.

Instead of the absurdist eye-rolling that defines a lot of Canadian humour – a perspective perhaps created by geography – Rakoff wrote with a perspective that came from urbanity. His cultural criticism was always sharp – he even wrote with insight on September 11th, and on his own disease in The Waiting, a New York Times article from 2011.

However, Rakoff's most memorable pieces come from his works of immersion journalism, in which he was stripped from the comforts of Manhattan. It's no surprise that two of his best essays are set in the wilderness (in one, he climbs a mountain in New Hampshire; in another, he goes on a terrifying woodland retreat). The image of Rakoff, a big city neurotic, encountering nature and its lovers was a great source of dramatic conflict. He bats down the upper-middle-class-liberal valourization of "getting away from it all" by reminding us that there's a good reason humans built the indoors in the first place.

Some people will forever connect Rakoff to David Sedaris, a writer to whom he bears a passing similarity, but also one to whom he literally owes his career, since Sedaris introduced him to This American Life's Ira Glass. Rakoff was a performer at heart, and the radio gave him a place to show it. In his appearances, Rakoff was always a fun counterpoint to Glass – while Ira's voice is inquisitive, Rakoff's confident, rich low tones were always droll, making him sound like the show's cool older brother. There are tons of gems in his back catalogue of contributions, and one of them has to be episode #329, "What I learned from television," when he decided to watch 29 hours of TV in a week, as much as the average American. Not just any 29 hours – he tried to sample everything on cable. Even when writing about the silliest topics – retro-futurism, Steven Seagal, crappy movies – his reporting was nothing if not thorough.

Rakoff's most recent book, Half Empty was a kind of thesis statement about his perspective as a writer, a deep look into the soul of a pessimist, and an argument that such a disposition was more practical than cynical. Capital New York called it "a portrait of a reporter in mid-sneer," but it was really a level-headed assessment of the ways people delude themselves. His takedown of the musical Rent is especially clear-eyed, as he suggests that, despite the show's supposition, AIDS does not make one "cuter and cuter." He took on a difficult subject with trademark dry wit, decrying the musical as a "middlebrow lie … posing as an antidote, like watching a sex-ed film narrated by gonorrhea." Rakoff learned that cancer had recurred in his body while writing the book, an irony in which even he found some humour.

Rakoff delivered his final book to his publisher a few weeks ago. Apparently, it is a novel written entirely in rhyme. Rakoff had done a few radio stories in metrical verse, including a very funny piece on Wiretap a few years back during which he played Dr. Seuss, and a touching short story on This American Life about a man who shows up at his ex-girlfriend's wedding and gives an ill-advised speech. Listening to pieces like these, one wonders if illness tempered his acid wit – the stories are slightly more sentimental than his other writing, but only slightly. The This American Life piece ends with an uplifting note, suggesting that, no matter how often we are run over by love, it's always worth trying again: "We're creatures of contact regardless of whether/ we kiss or we wound. Still, we must come together."

These stories may also be his most interesting, the ones that show his real search for honest emotion amid the sea of cultural garbage and personal hardships that he often wrote about. While Rakoff was a world-class grouch, his best pieces had a certain tenderness, and served as a humane reminder that there are rewards and dignity in perseverance, even when everything – in culture, in society, in your own life – kind of sucks.


"In the window, I fantasize about starting an entire Christmas Freud movement. Christmas Freud everywhere, providing grown-ups and children alike with the greatest gift of all: insight … People grumbling that it wasn't even Thanksgiving, and already stores are running ads with Christmas Freud's visage asking "What do women want … for Christmas?" (From Fraud)

"I go looking for Project Runway and find instead that the channel has been taken over by a show called The Real Housewives of Orange County. It's an all-day marathon. And yet, nothing happens. It is like watching paint dry – stupid, shallow, fake-breasted, Republican paint." (From This American Life, "What I learned from television")

Writing about his hiking boots, for a mountainous climb: "Just think, the shoes I wouldn't be caught dead in might actually turn out to be the shoes I am caught dead in." (From Fraud)

"The only thing that makes one an artist is making art. And that requires the precise opposite of hanging out; a deeply lonely and unglamorous task of tolerating oneself long enough to push something out." (From his essay on Rent in Half Empty)

"We're creatures of contact regardless of whether/ we kiss or we wound. Still, we must come together." (From his This American Life story "The Scorpion and the Tortoise")