Letterman proved to be a key figure in Macdonald’s career, a champion of the stand-up’s work (the talk-show host said no one was funnier) who booked the comic on his show’s final week. Macdonald, breaking from his trademark acerbic style, ended on a surprisingly moving tribute, displaying an emotional side that usually only lurked under the surface of his comedy.
In a column from 2017, I argued that what distinguished Macdonald’s comedy was his sensitivity to language, his peculiarly poetic brand of plain talk. He made stylish turns of phrase and folksy flourishes seem conversational and offhand. A lover of Bob Dylan, Macdonald was also a sponge for influences, borrowing and repurposing figures of speech or unusual words to create funny-sounding sentences.
But describing him as merely a master of joke writing misses his quickness, wryly deadpan delivery and, most of all, a unique level of commitment. He did not bail out of jokes and never pandered. You see this in his Bob Saget roast: the conviction to push through despite the confusion of the response. He pleased the crowd without being a crowd-pleaser. And no one had a nimbler and more assured sarcastic voice, which he used to find humor in ambiguity. There was a wonderfully odd moment on David Spade’s talk show a few years ago when Macdonald told Jay Leno he was maybe the best talk-show host ever, and no one, including Leno, seemed to be able to tell if he was being sincere.
There’s a lot of fun to be had in this liminal space between earnestness and just kidding. One of Macdonald’s most impressive feats is writing an entire memoir that remains there. It’s one of the greatest comedian memoirs but also a pointedly frustrating mix of fact and fiction, cliché and originality. It’s very funny, sometimes tedious, occasionally wise. The title, “Based on a True Story,” isn’t just a gag. It’s rooted in his faith that, as he puts it, “there is no way of telling a true story. I mean a really true one, because of memory. It’s just no good.”
Just because you can’t tell a really true one doesn’t mean that art can’t get closer to the truth. In an interview with New York magazine, Macdonald balked at the trend toward confessional art, saying he thought art was supposed to be about concealment. That was revealing.
The fact that he struggled with cancer for a decade was something he certainly didn’t advertise in his work. His death came as a shock to many. But clues were everywhere. Death has been among his favorite subjects in recent years. In a great viral moment, he delivered one of the earliest and best comedy club sets about the coronavirus. It was at the Improv in Los Angeles in March 2020 right before venues were shutting down. “It’s funny that we all now know how we’re going to die,” he said. “It’s just a matter of what order.”