Or, more precisely, previous attempts at career recovery never quite stuck. Dirty Work, the feature film Macdonald headlined the year he left SNL, bombed both at the box office and with critics (from the first paragraph of The New York Times review: “Phrases like terminally stupid and brain dead leap readily to mind). A Minute with Stan Hooper, with Macdonald in the titular role, was canceled after one season on FOX in the mid-2000s. Sports Show With Norm Macdonald lasted nine episodes on Comedy Central in 2011.

Macdonald on "Weekend Update" in 1995. NBC

Macdonald did enjoy some minor success with Norm, a sitcom that ran for three seasons on ABC (1999 – 2001). If you can ignore the obligatory laugh track, Norm, which costars a deliciously antic Laurie Metcalf, is pleasant enough, despite the inevitable clash between Macdonald’s anarchic nihilism and the neat, three-act structure within which it’s forced to exist. The pilot, for example, pivots on Macdonald—playing a disgraced former hockey player who becomes a social worker to avoid doing prison time for tax evasion—telling one of his clients, who is employed at a massage parlor, “You’re a huge whore!” One wonders how that moment would play without the pre-recorded guffaws that punctuate Macdonald’s declaration, if viewers were forced to sit with their discomfort—as they would be on a contemporary show like Louie. Then again: a great deal of Macdonald’s charm comes from his apparent refusal to give a fuck (one thing punk rockers were never good at: playing their instruments). It’s hard to maintain that façade while producing your own show.

Because as different as the Norm Macdonald of Weekend Update and the Norm Macdonald of the moth joke appear to be—the one dispensing absurdist non-sequiturs, the other waxing lyrical about an insect in existential crisis—what makes them both successful is the violent disregard they share not only for social niceties (hardly unusual in a stand up) but for expectations more generally. If Norm Macdonald has an ethos, it might boil down to: never do what is appropriate. Don’t tell the late night host a personal anecdote; don’t stop eviscerating your boss’s good friend; don’t tell the truth in your memoir; don’t be vulgar at a celebrity roast; don’t, in a golden age of political comedy, tell political jokes. Macdonald takes the contrarianism essential to comedy and carries it to its logical extreme. Consider not only the current popularity of stand up but the country’s interest in elevating norm-flouting blowhards, and the comic’s resurgent appeal becomes less mysterious.

At his best, Macdonald’s commitment to the unexpected provides a kind of thrill—the catharsis that comes with watching someone break a rule (about joke-construction, for instance) you realize in retrospect was pointless. But not all rules are made to be broken. There’s a reason comics are supposed to mock the strong at the expense of the weak: not only because it’s kinder, but because it’s funnier. Macdonald’s penchant for subverting expectations means that’s a dictum he’s happy to ignore—with occasionally queasy results.

In 1998, Macdonald hosted the sixth annual ESPY awards. His opening monologue is often cited as one of his most daring performances—and Macdonald does refuse to coddle his audience. At the end of his set, he singles out Charles Woodson, the first defensive player to win the Heisman trophy. “Congratulations, Charles,” Macdonald says, “that is something that no one can ever take away from you. Unless you kill your wife and a waiter, in which case, all bets are off.” The allusion to Simpson, also a Heisman winner, is meant to embarrass ESPN—but it comes at the expense not of a network executive, but of a twenty-one year old junior at the University of Michigan. On stage Macdonald is almost literally punching down.

Iconoclasm can be refreshing, even righteous—but not if it’s indiscriminate. Many comedians have realized this, moving away from rape jokes and gay jokes and jokes about “crack whores” (another of Macdonald’s preferred targets on Weekend Update), and toward bits aimed at those who can take it: people with power. To his credit Macdonald does mock himself plenty—his disgust for sex, especially while sober, comes up a lot. But he’s not above going for the easy joke, pandering to a crowd that wants to hear their prejudices affirmed. On Weekend Update, Macdonald once mocked a transwoman seeking to regain partial custody of her children. “Hmm, I wonder who’s going to win this case,” Macdonald mused, “the mother of the two children or the guy who had his penis twisted into a fake vagina.” I saw Macdonald deliver a joke only slightly less cruel during a stand-up set in St. Louis last September. That joke’s target was Caitlyn Jenner, and its oh-so provocative gist was that she was neither attractive nor “normal.” The casino crowd—by and large white, by and large middle-aged—roared.

Watch Now:

Kumail Nanjiani Tours Us Around His Mansion