Shane Gillis’s Fall and Rise (2024)

Shane Gillis has noticed that when he tells people his father watches Fox News they sometimes do something rude: they boo. Gillis is a standup comic, which means that he spends a lot of time at clubs in big cities, where he can seem a bit out of place. He is six-three and beefy, with a round head and small eyes that, he says, combine to make him look like Mimsy, a minor character from “South Park” who is too dull-witted to effectively throw his weight around. Gillis grew up playing football in Mechanicsburg, in central Pennsylvania, and he brings to the stage not just a lineman’s body and a coach’s mustache but a faint Pennsylvania accent, which he sometimes exaggerates for effect, and a much stronger Pennsylvania attitude, which he almost always exaggerates for effect. At first, he was surprised by audiences’ eagerness to boo his father, but soon he made it part of his act. “Don’t,” he warned a crowd in Austin, after mentioning Fox News. “I see you guys—most of you have Fox News dads.” He feigned consternation. “How dare you deny your fathers?”

The show was recorded and released as Gillis’s first special, “Live in Austin,” last year. Onstage, he is a convivial figure, but an unpredictable one: a beer-loving bro who is quick to let the crowd know that he is just joking—or maybe, unsettlingly, that he isn’t. Early in the special, he talked about the shock of moving to New York, where some of his new friends (“communists from Brooklyn”) liked to assure one another that they weren’t racist. Gillis was unimpressed. “Being racist isn’t, like, a yes-or-no thing,” he said. “It’s like being hungry.” He paused for two awkward seconds; the audience didn’t know whether this analogy would lead to a conclusion they could endorse. “It’s like, yeah, you’re not hungry right now. But a cheeseburger could cut you off on the highway. And you get hungry.” Now people were laughing, comfortable for a moment. Gillis took a swig of beer, tucked his chin, and dropped his voice. “The cheeseburger’s Jewish, in that joke,” he said. “No, no, I’m kidding,” he added, with a reassuring smile. “The cheeseburger is whatever type of cheeseburger you thought it was. In your racist heart.”

“Live in Austin” was not streamed by Netflix, HBO, or any other network. Gillis funded it himself, and released it for free on YouTube, where it has been viewed nearly seven million times, earning raves from comedy connoisseurs and practically no attention from the mainstream media. “Live in Austin” was both a début and a reintroduction: a chance for Gillis to make a fresh impression on people who had not thought of him since 2019, when for a few days he was perhaps the most talked-about comedian in the world.

The talk began on September 12th, when “Saturday Night Live” announced that it was hiring three new cast members, including Gillis, who was then a little-known standup and the host of an obscure podcast. In the hours after the announcement, an independent journalist named Seth Simons, who writes about the politics of comedy, unearthed a clip from the previous year, in which Gillis and his co-host, Matt McCusker, rambled about Philadelphia’s Chinatown. “It’s fuckin’ Chinee down there,” Gillis said, sounding baffled by the foreignness of the place. “Let the fuckin’ Chinks live there.” He said this second sentence out of the side of his mouth, seemingly impersonating a disdainful white politician from an earlier era. But he said it nonetheless, and the fact that he had uttered a racial slur soon became the one thing just about everyone knew about him. Several seconds later, talking about the neighborhood’s restaurants, he used a slang term derived from an imitation of a Chinese accent. “Fat white idiots like me are down there, suckin’ down nooders,” he said.

By the morning of September 13th, Gillis was at the center of a major news story. One of his fellow-hires was Bowen Yang, who was widely celebrated as the show’s first Asian American cast member; this summer he starred in “Fire Island,” an acclaimed queer rom-com. Compared with Yang, Gillis seemed to many observers like a throwback to the bad old days of comedy. (Over the years, some white actors have done Asian impersonations on “S.N.L.,” including Mike Myers, who portrayed a chuckling Japanese game-show host, and John Belushi, who played a chaotic samurai.) Gillis issued a grudging semi-apology, calling himself “a comedian who pushes boundaries,” and adding, “I’m happy to apologize to anyone who’s actually offended by anything I said.”

In retrospect, it was probably inevitable that Gillis’s invitation to join the show would be rescinded. More unexpurgated remarks were found, including Gillis’s description of Judd Apatow, the comedy auteur, as “gayer than ISIS.” (Apatow, who is not known to be gay, responded, “I don’t mind but I think ISIS probably feels bad.”) Lorne Michaels, the executive producer of “S.N.L.,” told me that he was and is a fan of Gillis, but that the network was concerned about a backlash. “NBC was in something of a panic,” he said. “It was, like, ‘They’re going to boycott these sponsors!’” On September 16th, he released a statement, saying that Gillis “will not be joining SNL,” and that his podcast comments were “offensive, hurtful, and unacceptable.”

A different sort of person in Gillis’s situation might have argued against censoriousness, casting himself as a defender of “freedom of artistic expression.” That is precisely what Dave Chappelle did, in his most recent Netflix special, which was less a standup routine than a lecture in which he addressed his many critics. But Gillis pointedly declined to plead his own case. “I don’t want to be a victim—I want to be a comedian,” he told Joe Rogan, the comic and podcast host, last year. “So I don’t want to come on and do stuff where I’m, like, ‘Yeah, it was unfair how I was treated.’ It’s like, no, I get it—I understand why I was treated that way. I said wild shit. I’m going to keep saying wild shit.”

Like countless comedians before him, Gillis relishes the sense of surprise generated by saying something socially inappropriate. (Decades ago, common profanity served this purpose; audiences today barely register George Carlin’s seven dirty words.) But Gillis’s brush with fame brought new followers, not all of whom seemed to understand what he was doing. One afternoon, in his apartment in Astoria, Queens, he recalled that after his firing he sometimes had to contend with audience members who prized offensive speech for its own sake: “Dudes would come up and be, like, ‘Chi-i-i-ink!’ I’d be, like, ‘No. That’s not it.’” The “S.N.L.” incident also endeared him to a cohort of politically conservative fans, some of whom probably had second thoughts when he joked onstage that, of all the American Presidents, Donald Trump would make the funniest assassination victim. (Fox News ran a story about the remark, noting that the White House had not responded to a request for comment.)

To anyone who thinks that comedians ought to prioritize non-stigmatizing language, or to be reliable allies for marginalized groups, Gillis might seem strikingly unreformed. He is, even now, the kind of straight guy who sometimes uses “gay” as a mild pejorative. But he excels at winning over skeptical audiences. When a joke gets a muted reception, he likes to look around the room and spread his hands slightly, in a “Ta-da!” gesture; the point is to acknowledge—and thereby shrink—the gap between what he thinks is funny and what the crowd thinks is funny. In November, Gillis is scheduled to headline Town Hall, as part of the New York Comedy Festival. Meanwhile, he is perfecting a new hour that includes a long, carefully calibrated story in which he interrogates his feelings about slavery and the Founding Fathers.

Gillis’s unpredictable comedy can make his peers seem dull by comparison. The comic Jerrod Carmichael—whose melancholy recent special “Rothaniel” attracted unanimous critical acclaim—considers Gillis one of the few truly funny standups working today; this summer, he drove from Los Angeles to Irvine to watch him perform. “His material still feels dangerous,” Carmichael told me. “It’s because it’s truthful, right?” Back in 2019, a prominent YouTuber named Jenny Nicholson tweeted, in exasperation, “Was SNL hurting for ‘guy in your boyfriend’s friend group who always says inappropriate things but your boyfriend insists he’s known him forever and he’s a really nice guy’ energy.” Evidently not. But, like most great comedians, Gillis has found a way to be thoroughly and recognizably himself onstage: he makes audiences feel that he’s not pretending to be any better or worse than he actually is.

Gillis’s career began in earnest less than a decade ago, when he was living in Philadelphia and performing at Helium, a subterranean theatre that is the nucleus of that city’s standup scene. This summer, he returned there for a weekend of sold-out shows. It was a triumphant homecoming: friends from the local scene served as his warmup acts, and the bar was selling a Fuck S.N.L. cocktail—not Gillis’s idea, he hastened to explain. These were Gillis’s people. During his set, they whooped when he requested a fresh Bud Light. When he confessed that he missed Trump’s press conferences, because they were “fun,” he heard a cheer in the crowd. “No, no, no—chill the fuck out,” Gillis said, jovial but firm. In his view, partisan cheering is just as inimical to comedy as partisan booing. Gillis tries never to inspire “clapter”—the sound of an audience broadcasting approval, rather than enjoyment.

When his set was over, Gillis held court in the theatre bar, where he was approached by a stream of exuberant young men. One bought him a beer and asked for a picture in return. Another said, “Not to sound gay, but I’m a big fan.” An old friend urged Gillis to do a shot, but he was distracted by a glassy-eyed admirer, who wanted him to record a message for a friend: “Let’s make a video and tell him, ‘You missed out, bitch!’”

“I don’t want to do that,” Gillis said, softly.

“No, he can take it—he’s a dawg,” the fan insisted. Avid listeners of “Matt and Shane’s Secret Podcast,” which still releases episodes weekly, are known as “dawgz”; a dawg is essentially a bro, only better.

“I don’t want to make fun of him,” Gillis said, and the fan settled for a photograph.

Gillis used to be frustrated by having to perform in front of audiences full of young men whose enthusiasm outstripped their comedic discernment. (He would sometimes think, “Please, dude—I’m trying to be good at standup.”) As his crowds have grown, they have grown somewhat less homogeneous, and he sometimes jokes about seeing stone-faced women who seem to have been dragged to the club by their podcast-loving boyfriends. Comedy podcasts have been important to his career, and in the aftermath of 2019 he bolstered his following by appearing on a number of them. These shows tend to be contemptuous of the decorous sensibility of the mainstream entertainment industry, and they often purport to be speaking for a counterculture, although the numbers suggest that the “counter” may in fact be bigger than the “culture.” Joe Rogan’s show, which hosted Gillis for the first time last year, reportedly reaches something like eleven million listeners—about twice the typical audience of “Saturday Night Live.” Gillis’s podcast has hundreds of thousands of listeners, many of whom pay one or five or ten dollars a month for access to bonus content. And for two weeks this summer he was part of a tour headlined by Bert Kreischer, a gregarious comic who is also the host of “Bertcast,” a podcast devoted, as many of them are, to long discussions of nothing in particular. The tour played mainly arenas and minor-league baseball stadiums; if this is niche entertainment, then so is just about everything else.

On a podcast, unlike onstage, Gillis is unscripted, and only intermittently hilarious; he says he views podcasting as a supplement to his real profession, which is being a standup comic. But it’s not clear what people want from standup comedy these days. The form is as prominent as it has ever been, and as divisive. There may be no comic more popular than Chappelle, whose routines about trans identity have sparked protest and backlash. (His specials earn him eight-figure checks from Netflix, but a recent performance at a theatre in Minneapolis had to be moved at the last minute; the venue suggested that hosting Chappelle would be incompatible with creating the “safest” possible environment.) And some of the most acclaimed specials of recent years have treated standup itself with suspicion: in 2018, the Australian comic Hannah Gadsby released “Nanette,” in which she suggested that comics and their audiences were trapped in “an abusive relationship.” She explained, “Punch lines need trauma, because punch lines need tension, and tension feeds trauma,” and added that she might need to “quit comedy.” (Happily, she didn’t.) Meanwhile, late-night hosts like Stephen Colbert and Jimmy Kimmel are now known less for telling jokes than for delivering earnest liberal commentary. A few days after Hillary Clinton lost the 2016 election to Trump, “Saturday Night Live” began its broadcast with Kate McKinnon, dressed up as Clinton, singing a thoroughly laughless version of Leonard Cohen’s “Hallelujah”; nowadays, the show tends to depict Joe Biden, rather sympathetically, as an aging normie, a more or less sane man in a mad world. Often, the implicit message is that we are living in a tragic era, not a comic one.

Gillis remembers the shock of performing on November 8, 2016, as it became clear that Trump had been elected President. “People were, like, crying onstage,” he says. “So I went on and I was, like, ‘We’re back, dudes! White dudes are back—let’s go!’ Like, obviously an insane thing. But people were mad. Which, I guess, is why it’s funny.” Gillis professes to be incredulous that anyone would worry about a comedian’s political convictions. (One afternoon, at lunch, he likened himself to the guy who brought him a sandwich. “It’s like being mad at a waiter,” he said.) But he often tells audiences, as a conciliatory gesture, that he never voted for Trump. He jokes that this took considerable restraint, given that he felt Trump was targeting his particular demographic. “His whole campaign was at me,” Gillis once said. “He was, like, ‘Are you a fucking fat idiot?’ I was, like, ‘Yeah, dude! Yeah—what are we doing? What the fuck are we doing, dude? We’re building walls? Hell yeah!’” He has developed an uncannily good Trump impersonation, one that is neither an endorsement nor an indictment. He reliably gets a big laugh imitating Trump as he brags about the elimination of an Islamic militant by bellowing, “He died like a dog.” It is an absurd moment, but not a fictional one: this is exactly what Trump said, in 2019, when he announced the death of Abu Bakr al-Baghdadi, the ISIS leader.

During the pandemic, Gillis resolved to bring his Trump impersonation to the screen. He and a comedian friend from Philadelphia, John McKeever, used their own funds to film twelve sketches, including one that drops Trump into a speed-dating session; they uploaded them to YouTube, where “Trump Speed Dating” has been viewed more than two million times. The show is called “Gilly and Keeves,” and the two recently shot a second season, which they plan to sell online. Gillis enjoys the freedom of being a do-it-yourself comedy star, but he also wouldn’t miss being his own marketer and distributor if a big media company decided to write him a check. In the meantime, standup provides him with both structure and community, so when he is not on tour Gillis can often be found at the Stand, a club in Union Square, or at the Comedy Cellar, a Greenwich Village institution. Passing through the Cellar’s doors sometimes feels like returning to an era before social media: in an effort to make sure nothing goes viral, bouncers require patrons to seal their phones in bubble mailers, which the club purchases by the pallet. (The mailer is not entirely impregnable, but it makes a conspicuous squeaking sound if someone tries to rip it open mid-set.) Most nights, an atmosphere of cheerful indiscretion prevails, and during one recent appearance Gillis was introduced by an m.c. who had previously delivered a series of ribald jokes about gay sex, sometimes punctuated with the snap of a folding fan. Welcoming Gillis, he told the crowd, “Your next act has a dick I think about all the time.”

Gillis, bounding onstage with a can of blackberry hard seltzer, said, “If he knew what my dick looked like—aw, he’d be sad.”

Fans of Gillis often tell him that he reminds them of someone from their home town, which might be a polite way of saying that he doesn’t much resemble a celebrity. “You see a guy like me on TV, he’s usually doing something pretty bad,” Gillis says. The word he uses to describe his appearance is “oafy.” Growing up in Mechanicsburg, he was known as a big guy who liked to drink beer; at thirty-four, he works hard to maintain this reputation. Over the summer, he appeared on a drinking-game podcast hosted by Barstool Sports. Gillis, wearing a Phillies jersey and face paint that resembled an Eagles helmet, helped his team win by downing something like sixteen beers in sixty-three minutes.

Forty-eight hours later, he was horizontal on his couch in Astoria. “I kind of hate myself right now,” he told me. “My girlfriend’s out of town for, like, a week, so the place is trashed.” It actually looked perfectly respectable: American-history memorabilia on the walls; ESPN, muted, on the television; a package from Sheath, an underwear company that sponsors Gillis’s podcast, on the table. He was using comedy to distract himself from how lousy he felt. “Last night I did seven sets,” he said. “I needed to kill seven times to feel better.”

Like most kids, Gillis knew about comedy long before he knew about comedy clubs. His father, who sold food-packaging equipment, had some George Carlin CDs, but Gillis was more drawn to high-energy comics like Carlos Mencia and Dane Cook, who were ascendant in the early two-thousands. Most of all, he remembers watching “Old School,” the 2003 Will Ferrell movie, and thinking that he could do what Ferrell was doing, though he didn’t know how to start. After high school, he was recruited to play football at West Point, but he quickly realized that he did not enjoy the gruelling team workouts. He transferred to a less exacting program at Elon University, in North Carolina, where he spent a year practicing with the team and neglecting his studies; he was asked to leave, and found himself back in his parents’ house, going to community college and washing dishes.

“I’m not a mad scientist—I’m just a disappointed scientist.”

Cartoon by Charlie Hankin

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Gillis eventually earned a degree, in history, from West Chester University, outside Philadelphia, where he started doing comedy at a local bar; he learned first that it’s a bad idea to go up with nothing prepared, and then that it’s nearly as lethal to go up with a rote routine. He worked for a while selling Hondas, and spent six months teaching English in Spain. But he was obsessed with standup, and gradually learned to command a room; in the summer of 2016, he won the annual Philly’s Phunniest competition, which was about as far into the future as he had planned. People from beyond Philadelphia began to take note, including Dan Soder, a comic and an actor who met Gillis at Helium and eventually took him on the road as his opening act. It seemed to Soder (who now plays Dudley Mafee on “Billions”) that Gillis was already “fully formed.” He told me that Gillis would walk onstage, grab the microphone, and say, matter-of-factly, “Hell yeah.” It made him seem less like a performer than like a friendly guy at the bar, one whom audience members already knew.

In Philadelphia, Gillis had befriended Matt McCusker, a fellow-comic, and they spent enough time trying to make each other laugh that they figured they might as well set up some microphones and start a podcast. They are a complementary pair. Where Gillis likes beer and sports, McCusker is a devoted pothead with a fondness for dubious schemes and theories; he has a master’s degree in social work and, nowadays, a wife and two children. Their podcast has always been extremely casual, and extremely intimate. They recorded a recent episode lying in a hotel bed together, trying to recover from whatever they had done the previous night.

The appeal of this kind of podcast is that listeners, if they have the patience to sit through hours of idle banter, get a chance to hear something uncensored and unfiltered—just two guys talking. In this case, those guys are also comics, and sometimes you can sense that they are trying on different points of view, rooting around for one that might be funny. When McCusker mentioned the exuberance of Pride celebrations, Gillis said, with exaggerated umbrage, “It’s a jizz parade.” Then they reconsidered.

MCCUSKER: I get it. I feel like they got bullied pretty hard.

GILLIS: They got bullied, and now they’re out dancing in the street, saying, “Fuck you!”

MCCUSKER: They are dancing in the end zone.

GILLIS: They’re showboating a little. Good for them for that, honestly!

MCCUSKER: It’s true.

GILLIS (coachlike, increasingly heated): You wanna keep ’em from celebrating, dude? Don’t let ’em score. Don’t let ’em in the end zone. They scored already. They’re allowed to dance.

This kind of talk is certain to offend plenty of people, virtually none of whom are likely to be regular listeners of “Matt and Shane’s Secret Podcast.” Such is the allure of shocking content: it can turn those who enjoy it into insiders, united against those outsiders who don’t. In this sense, Gillis and countless other provocative comics and podcasters are descendants of the so-called shock jocks, radio personalities who inspired loyalty precisely because of their determination to violate taboos. Younger listeners who know Howard Stern as a thoughtful celebrity interviewer are sometimes startled to hear old recordings of him bantering with a Klansman, or asking women profoundly inappropriate sexual questions.

“Opie and Anthony,” which began broadcasting in 1995, cultivated a more scabrous sensibility, and a closer relationship with standup: in the two-thousands, the hosts organized an annual comedy tour. Anthony Cumia was fired from the show in 2014, for provocations that were more angry than funny. (After what he said was an altercation with a Black woman in Times Square, Cumia posted a picture of the woman, along with the words “animal pig face worthless meat sack.”) He subsequently launched his own streaming network, Compound Media, which was the home of “A Fair One,” a podcast that Gillis used to co-host.

One of the things that Gillis learned in 2019 is that comics should expect to be judged by whatever they say on podcasts. Compared with the old shock jocks, though, today’s provocateurs can seem positively erudite. Stern sometimes tried to coax women guests to sit on an ottoman-size vibrator he had in the studio; Rogan recently spent two and a half hours talking to the theoretical physicist Michio Kaku. The regulatory environment has changed, too. Stern’s show was repeatedly fined by the Federal Communications Commission. His heirs worry less about government action than about the complicated mixture of approval and outrage they inspire among members of the general public, and among the corporations that often determine the limits of acceptable speech.

Gillis doesn’t complain, because he recognizes that part of what makes taboo humor funny is that it is, in fact, taboo—which means that comics who argue against linguistic taboos are usually being hypocritical, or at any rate self-defeating. During a recent podcast appearance, he acknowledged that certain jokes rely for their impact on the idea that someone, somewhere, might be upset by them. “If literally there would be zero blowback for going on a podcast and being, like, ‘Here’s some funny things about Hitler,’ it’s not as dangerous,” he said. “It’s not as funny.”

Gillis was not quite as surprised as the rest of the world when he was hired by “Saturday Night Live,” in 2019. By then, he had signed with United Talent Agency and moved to New York, and that summer he performed at high-profile showcases in Montreal and San Francisco, where he presented himself as a red-state emissary to a blue city. (He teased the crowd about the election: “Do you guys remember how, like, confident you guys were, going into that last one?”) In 2019, Variety reported that Lorne Michaels had brought in Gillis as part of an effort to “appeal to more conservative viewers.” Michaels denies this, but he allows that Gillis does provide a different point of view. “He’s from a part of the world that should also have a voice,” he told me. “He’s very funny. And he’s good with language, which I always look for.”

Gillis knew he had probably said more than his share of offensive things over the years, but he couldn’t quite remember what, and he says that representatives of the show told him he had passed a background check. For five or six hours, he could enjoy the idea that he had joined the most venerable institution in American comedy; as a boy, he had wondered how a regular guy becomes Will Ferrell, and the shortest answer is probably “Saturday Night Live.” Then he heard from someone at his agency, asking if he had ever used the word “Chink.” Gillis’s response was “Of course not!” But his memory was soon jogged by the video clip that Seth Simons had found and posted to Twitter. Simons says now that he was less worried about Gillis than about the fact that a cohort of comics seemed to think it was fine—or even cool—to use offensive and dehumanizing language. “I don’t think he is, at all, the worst offender in that world,” Simons told me. “But I think he is part of a culture that believes in, just, total impunity for going out and saying a bunch of slurs on your podcast.”

Bowen Yang did not comment publicly, but plenty of other performers did. The actor Daniel Dae Kim, from “Lost” and “Hawaii Five-0,” wrote, “It took 45 years for @SNL to get an East Asian cast member and in that same year he’ll be joined by someone who would have no problem calling him a ‘fuckin’ chink.’” Another actor, Simu Liu, from Marvel’s “Shang-Chi and the Legend of the Ten Rings,” wrote, “This word has been used to dehumanize my people for over 150 years. You don’t get to use it in the name of edgy comedy.”

Gillis’s first public statement, about being “a comedian who pushes boundaries,” sounded ridiculous to many people—including Gillis, who has since apologized for saying something so pretentious. The argument over his firing was not about free speech; it was about what sort of performers “Saturday Night Live” should hire. Not many people knew enough about Gillis, or his work, to defend him. A few of the show’s veterans spoke up on his behalf, on principle, including Norm Macdonald, who lived by the creed that comedians should be troublemakers, and Rob Schneider, who wrote that we were living in an era of “cultural unforgiveness,” and suggested that Gillis was being unfairly punished for “comedic misfires.” (Schneider, who joined “S.N.L.” in 1990, is sometimes described as the show’s first cast member of Asian descent; his maternal grandmother was Filipina.) But there was no public outpouring from people insisting that the show should keep a cast member who had uttered a racial slur.

Gillis remembers those days as a surreal blur of frantic meetings and phone calls and texts; U.T.A. dropped him as a client, while clubs like the Stand kept booking him. If anything, the episode made him more devoted to comedy, because he wanted to prove that he really was funny. It was during this period that a friend put him in touch with Louis C.K., whose tenure as one of the country’s most widely admired comics ended suddenly in 2017, after five women accused him of sexual misconduct. C.K. discovered, as Gillis has, that he could keep doing standup despite public opprobrium. (This year, he won a Grammy for “Sincerely Louis C.K.,” a self-released special; the award suggested that there is a considerable gap between what show-business professionals say in public and how they vote in private.)

C.K. considers Gillis a “great comic,” and loves watching him watch the audience, registering people’s delight or dismay. “He has a fishbowl face,” C.K. told me. “Like, you can see what he’s feeling all the time.” Gillis and C.K. are now close, and they recently collaborated on a marathon podcast in which they attempted to discuss all forty-five American Presidents; it lasted nearly six and a half hours. Another of Gillis’s fans is Andrew Yang, the former Presidential candidate, who argued in 2019 that Gillis deserved a second chance. This seemed like a political stratagem (Yang was positioning himself as a candidate who could unite a divided America), but the two stayed in touch. Gillis recently appeared on Yang’s podcast, where Yang told him about how he used to fight schoolmates who teased him for being Asian American. And, in San Francisco this summer, Yang introduced Gillis before a performance, and tried out some comedy himself. “I first met Shane when I was running for President of the United States and he was trying to join the cast of ‘S.N.L.’—and we both fell short,” Yang said. Then he turned serious, delivering the kind of heartfelt message that Gillis avoids at all costs. “Through everything,” he said, “Shane has kept his spirit, stayed true to himself, honed his craft, became a better human being and a better comedian.”

Among some of his peers, Gillis is now viewed as an expert on what can and can’t be said. Theo Von, a garrulous Louisianan, hosts one of the most popular comedy podcasts on YouTube, and when Gillis paid a visit last year Von paused in mid-conversation to ask, “You feel like we’ve said anything cancellable?” Gillis didn’t think they had, but an hour later he issued a warning. Von was talking, for no good reason, about Lester Holt, the host of “NBC Nightly News,” who is Black, and who is known for his careful diction. “I feel like Lester Holt’s secretly a white guy,” Von said. “You telling me that’s not a white guy in blackface?”

Gillis demurred: “This type of thing is a little dangerous. Speculating on a Black guy’s race?”

Von tried a different tack. “In the future,” he said, “everybody’s going to be beige, and it’s going to be ridiculous we were ever even arguing about race stuff.”

Again, Gillis demurred: “It’s funny for white people to say that, though. To be the purveyors of racism for the longest time, and then towards the end be, like, ‘What are we even fighting about?’” He laughed, and added, “It’s good for the honkies, trying to hit the Eject button.”

Gillis has now had three years to think about linguistic taboos. But he is less interested in right and wrong than in audience reactions: which words are distracting, which words make a joke less funny instead of more. “I definitely don’t say the F-word onstage—I really try not to,” he said, referring not to the common expletive but to the anti-gay slur. During a recent episode of Rogan’s podcast, Gillis did an impression of an obnoxious drunken tourist in Hawaii, slurring, “You’re from a fuckin’ island, faggot,” and then caught himself. “Delete that—my bad,” he said.

One lesson from Gillis’s experience might seem simple enough: Don’t use racial slurs. But what about sexual slurs? Almost no one calls for male comics to be censured for saying “bitch.” And what qualifies as a race, anyway? Gillis recently filmed a sketch for “Gilly and Keeves” that consists of almost nothing but Italian American stereotypes; the underlying joke is that, in the current political environment, you can say whatever you want about Italian Americans. It is probable that the more taboo words there are, the less consistently the taboos will be honored. And it seems certain that there will always be comedians and audiences who revel in the illicit thrill of bad words, no matter how we define “bad.”

Hannah Gadsby is right: punch lines need tension, which means that comics must often find ways not just to tolerate tension but to generate it. Gillis will sometimes play the role of the angry conservative, if he’s talking to a liberal, or vice versa. This summer, onstage with the right-leaning comic and producer Adam Carolla, he responded to a joke about abortion with an unexpected blast of feminist sarcasm. “We could let women decide—nah, I’m fuckin’ around,” he said. “What, are we fuckin’ nuts, dude? Don’t let them make choices.”

Gillis is in some sense a purist: he cares more about standup than about anything else. That means he would rather be funny than correct. It also means he recognizes that there is more to standup than just making people laugh. Gillis’s heroes are performers like C.K. and Chris Rock, who were widely celebrated not just for their punch lines but for their insight. It is probably thanks to these performers that so many people now take comedy seriously—more seriously, sometimes, than comedians might prefer.

The second season of “Gilly and Keeves” had its première in person, at the Theatre of Living Arts, in Philadelphia. Gillis and McKeever sold out two performances in one night, even though they weren’t quite sure what they had signed up to do. Gillis emerged, squinting into the audience. “During rehearsals, we were, like, ‘We can just fuckin’ wing it,’” he said. “It’s a lot different when these chairs are empty.”

For about an hour and a half, the two screened their new sketches, which were closer in spirit to “I Think You Should Leave with Tim Robinson,” the unhinged (and sometimes menacing) Netflix series, than to “S.N.L.” Gillis’s Trump reappeared, in a sketch about desperate film producers who can’t find anyone to play Hitler in their movie; Trump takes the role and takes over, doing his best to turn Hitler into a character that audiences will root for.

They got through the first show, and then emptied and refilled the theatre to do it again. After the second show, Gillis led a dozen friends and collaborators down South Street, looking for someplace to drink. He was stopped by a pair of police officers, who recognized him from YouTube and asked for a selfie. “We were just talking about ‘Uncle Daycare,’” one of them said. He was referring to a “Gilly and Keeves” sketch about a crew of moronic white guys who are sent to learn basic life skills: how to debunk vaccine conspiracy theories, for instance, or how to refrain from harassing underage girls.

One theory of Gillis’s career is that it mirrors a cultural and political divide within comedy. Maybe audiences increasingly expect comedy to reflect their own beliefs, priorities, and identities. By some metrics, “Saturday Night Live” is as diverse as it has ever been, and perhaps as politically partisan, too. In alternative rooms, where a new generation of performers embrace surreal humor and insist on the importance of identity, old-fashioned joke-tellers like Gillis are sometimes known, not always admiringly, as “club comics.” Meanwhile, Rogan and a whole cohort of comics and podcasters, many of them white and male, find big audiences by pushing back against the perceived hypocrisies and excesses of liberal culture. Everyone can feel comforted by the thought of watching something someone else would hate.

In a “Saturday Night Live” sketch from this season, which was cut from the broadcast but posted on the YouTube page, the cast members seemed to be mocking people like Gillis. John Mulaney, the host, played a man who had just lost his job for having made inappropriate comments. “I guess I should have deleted my old podcasts,” he lamented. Then the mood brightened, and a voice-over cut in, advertising a useful product: the Fisher-Price Podcast Set for White Guys. You could rant all you liked, secure in the knowledge that the microphone was fake, so that nothing was actually being recorded. By the end, Mulaney’s character was happily playing with his new toy. “I can say whatever I want, and I can never get cancelled,” he said. “Even the N-word!” This was a witty expression of anti-anti-cancel culture. It was also a demonstration of the appeal of linguistic taboos: the phrase “the N-word” carries just enough transgressive power to make the sketch funnier.

The promise of comedy is that a truly great joke, a truly great performer, is undeniable, almost no matter who you are. And Gillis’s standup does not seem to be particularly polarizing, at least not if you compare him with Chappelle, or with Ricky Gervais, whose most recent special includes a punch line involving an exaggerated Chinese accent. In the industry, comics pay close attention to who can make a crowd laugh so hard that people are gasping for air, and who can reliably fill venues around the country. Gillis is already known as the first type of comic, and he seems to be in the process of becoming the second. He recently signed a deal to do his first national theatre tour, starting early next year. “So few people are good at their craft,” Jerrod Carmichael says. “No matter what you identify as—as a woke comedian, or anti-woke comedian, whatever—none of that really matters. Just sell tickets. Be interesting and sell tickets.”

One night not long ago, Gillis was in a cramped hallway in the basement of the Comedy Cellar, which is lined with photographs of famous comics—not including him, at least not yet. He was working on a tricky and possibly ill-advised joke about the sexual orientations of people with Down syndrome. (He says, if it matters, that he has a relative with Down syndrome, and that he has spent time as a Special Olympics coach.) Audiences didn’t like it, but Gillis was sure he could make it work, and so he kept at it. During his set, it failed again, and he seemed both frustrated and amused. Mostly, though, he killed, expertly creating and resolving moments of discomfort. He was a bellicose patriot one moment, a terrorist sympathizer the next. The crowd seemed unsettled, not quite sure where he was coming from, but everyone laughed.

Rich Vos, a veteran who has been performing for nearly forty years, watched from the hallway and shook his head. “He got so fuckin’ funny,” he said.

Liz Furiati, the general manager, was standing next to him, and she agreed. “It’s disturbing,” she said, and she meant it as high praise.♦

Shane Gillis’s Fall and Rise (2024)
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