News of the death of the comedian Norm Macdonald, on Tuesday, at sixty-one, from cancer, came as a blow to me. I met Macdonald only once, in 2018, when I spent a day with him for a Talk of the Town story—but it was a long day, and I remember wishing that I could offer him the column inches to match. Macdonald was gearing up to release a series on Netflix, a kind of inside-out talk show unimprovably called “Norm Macdonald Has a Show,” in which all the normal audience-pleasing constraints of production had been pointedly erased. He happened to be doing some standup performances in San Jose, California, and I happened to be in San Francisco, so I came down with my notebook on the morning train. The plan was for us to meet at his hotel and go to the Winchester Mystery House, one of the local tourist attractions—possibly the only local tourist attraction—and, I hoped, a useful backdrop if our interview turned out to be a dud. It wasn’t. Macdonald met me in the hotel lobby wearing sweatpants, sneakers, and a saggy orange polo shirt. He had just woken up. His twentysomething assistant, John Steere, led him to a meat sandwich and a bowl of dip, and he scarfed that down as I fretfully watched the clock. By the time we’d piled into an S.U.V. and arrived at the Mystery House, we’d missed our slot, so we shrugged and turned around. That was when I realized that, as far as the day went, I was less a reporter cornering an interview than a writer on the Norm train, along for the ride.

Like many people my age, I knew Macdonald chiefly as the host of “Weekend Update,” on “Saturday Night Live,” in the late nineties. (One of the current hosts, Colin Jost, has described Macdonald as his leading model in the role.) Also like many people my age, I’d sort of lost track of him in the decade or two since then, a period during which he brought out three seasons of his own sitcom (“The Norm Show”), a popular interview podcast (“Norm Macdonald Live”), and a comic novel written as a faux memoir (“Based on a True Story”). He fell back into my awareness with a Netflix special, in 2017, called “Hitler’s Dog,” which struck me as a masterwork of the form.

Semi-dissipated middle age suited his style. Macdonald was a Canadian who had cut his teeth as a writer on “Roseanne,” and his jokes tended to take their frames from a hard, dry TV Guide-and-flannel shtick. (“You know how they say guys have ‘gaydar’—they can see other gay people? I’m like that with guys at my same level of smartness,” goes one of his setups in “Hitler’s Dog.”) Yet he was a performer as much as a writer, and his mature style turned on a rich vocabulary of pauses, ironized niceties, and smirks set against his zonked-seeming deadpan. No one was better at stringing out a joke between its setup and its punch line. The purest instance of the skill might be his famous “moth” routine, in which he took a lame stock joke (“A moth goes into a podiatrist’s office . . .”) and, by delivery alone, built a three-minute meta-gag on top of it, working his audience all the way.