These clips show why Norm Macdonald was the best worst talk show guest of all time

It’s one of the ironies of late-night talk TV that the people who are typically handed the reins of that most formulaic, corporate synergy-heavy branch of television are usually comedians, a group of people who do not, as a rule, like being told what to do. And yet, more often that not, they do it: Playing nice, promoting their owners’ projects, and generally coloring within the comedy lines that keep the people signing the checks, and the stars they funnel toward TV’s collective late night couches, happy.

Norm Macdonald was constitutionally incapable of playing that game, which might explain why he didn’t get a talk show, at least not until the far looser worlds of podcasts and streaming TV made it a possibility—and why, at the same time, he was such a frequently sought-out guest on the talk shows of others. Casually capable of precision cruelty, and endlessly mischievous, Macdonald was the embodiment of the chaos so often scrubbed out of the late-night world, and which its most iconoclastic hosts—especially Conan O’Brien and Dave Letterman, both devoted fans—clearly, dearly craved. It helps explain why so many of the moments being passed around online today, in the wake of Macdonald’s death, have come from his numerous talk show appearances, dropping in to let his more ostensibly successful friends live vicariously through a man who would relish explaining the logic of a premature ejaculation joke for an audience of millions.

That, of course, is a reference to Macdonald’s 1997 appearance on Late Night With Conan O’Brien, a high-water mark in the art of being mean to Carrot Top and Courtney Thorne-Smith on screen. In addition to containing the three funniest words Macdonald ever said, it’s also a masterclass in not giving a shit about late-night convention, as Macdonald all but dares O’Brien to join him in roasting his other guest.

Macdonald’s other favorite Conan-adjacent past-time? Telling the longest, most convoluted jokes imaginable. But even then, it wasn’t just about the incredibly hokey, violently banal punchlines Macdonald delighted in delivering: It was the sheer, obvious joy of him wasting such massive swathes of TV airtime, driving O’Brien to madness as the looming “joke” got closer and closer. In the hands of a less masterful comedian, it’d be tedious as hell, but from Norm, it was sublime—a similar experience to watching his famed performance at Comedy Central’s Bob Saget Roast in 2008. In a handful of minutes, Macdonald delivered one of the most quietly effective “fuck you”s imaginable to the concept of roasting itself, all without raising his voice or dropping a punchline that would’ve felt out of place in Reader’s Digest. Amid the usual cavalcade of foul-mouthed burns, Macdonald somehow made his deliberately cornpone comedy the most brutal punch of the night.

It’s not hard to find footage of Macdonald making other comedians crack up, often by pushing past the accepted bounds of comedy—like this clip of him on The Daily Show, doing a casual set of material on the death of Steve Irwin 10 whole days after it happened. (“Please don’t make me laugh at this,” Jon Stewart begs, futilely.)

Or a more recent bit from Comedians In Cars Getting Coffee, where you see the typically composed Jerry Seinfeld completely lose his shit at Macdonald’s take on the Bill Cosby case:

Nobody, though, matched the late-night vibe of Norm Macdonald better than David Letterman—and not just because Macdonald loved mimicking his TV hero during his old SNL days. (Demands of “You got any gum?” still resonate in our ears.) You could always tell when Letterman was enjoying himself in an interview—the lean-in, the hungry, “Yeah, what do you got?” smile—and it’s all over the hours of couch time he and Macdonald got over the years, stretching all the way back to Macdonald’s very first TV comedy appearance on Letterman’s stage in 1990. It’s all there in his final appearance, too, from 2015, in which Macdonald—among the most reserved men in comedy—genuinely starts crying over the end of Letterman’s legendary show.

Norm Macdonald was a terrible talk show guest, from the point of view of anyone trying to make money off a talk show—and it made him one of the greatest talk show guests of all time.