Pro-Trump Comics Poke ‘Woke’ in the Eye and Find a More Receptive Home in the Mainstream

If there was an effort to make stand-up comedy a bit more genteel a few years ago — with offensive words and phrases placed out of bounds — a second Trump administration has emboldened more transgressive voices who are willing to wind it back to the days when it was fine to have a laugh at the expense of women, trans people, people of color and the mentally disabled.

Tony Hinchcliffe generated a wave of controversy at a pre-election Trump rally when he called Puerto Rico “a floating island of garbage.” Shane Gillis was fired by “SNL” when audio surfaced of his homophobic comments and his use of derogatory term for Chinese people. Matt Rife drew heat for jokes in a Netflix special about domestic violence, quipping of a restaurant hostess, “If she could cook, she wouldn’t have that black eye.”

Comics like Gillis, Rife, Hinchcliffe and Theo Von possessed loyal audiences even before Donald Trump’s reelection, but now they seem to be finding wider opportunities. With Trump back in the White House, Hinchcliffe has signed a deal with Netflix for three “Kill Tony” comedy specials. Gillis has hosted “SNL” twice since his dismissal, and has made two specials for Netflix in addition to starring in his own sitcom, “Tires.”

Amid a wave of pushback against “wokeness” as well as efforts to broadly dismantle diversity, equity and inclusion policies, the question of where “the line” gets drawn appears to have shifted.

“You can offend a bunch of people, but if you still have enough fans to support you, and if streamers feel like that would help their subscription base, they might want your content on their platform,” said Wayne Federman, an L.A.-based comedian and actor who is also a professor at USC. “It’s as simple as that. It is just a numbers game.”

“Attention is attention,” a female executive at a major streamer, who asked not to be named, told TheWrap. “Hinchcliffe was selling out The Forum well before we knew who Tony Hinchcliffe was. We might think that these guys are fringe, and now they’ve come into the mainstream. More people now cover them because of the political environment we’re in.”

Changing Perceptions

The perception that comedy has been shackled by “woke” attitudes hasn’t been confined to the fringes of the stand-up world. Jerry Seinfeld, for example, griped on a New Yorker podcast last year about the “extreme left” and “PC crap” having homogenized network sitcoms, before walking that back in an interview with Entertainment Weekly in October, acknowledging that culture changes before adding, “You can’t say certain words, you know, whatever they are, about groups — so what?”

In 2021, Gillis told pal Von that he didn’t contest being fired at the time “because those are today’s rules.” But the rules are being rewritten, not just for Gillis, but comics like Hinchcliffe.

Per their publicly stated politics, Hinchcliffe and Von are firmly in the Trump camp, but in”Beautiful Dogs,” Gillis said that he’s not a Republican … “yet.”

Meanwhile, Rife celebrated when Trump lost the 2020 election, calling for his social media followers to “give this fat turd the goodbye he deserves.” By 2023, his public persona had changed so much that one female IG user commented, “Well, this didn’t age well.” And by 2024, Marc Maron described him as “the new It Boy of s–ty comedy” who “s–t on the mostly female audience that he accumulated through social media to kiss up to these pseudo edgelords.”

Not all comics that have lamented the influence of “woke” culture fall into the conservative camp. In some instances such as Bill Burr and Bill Maher they have simply grown tired — or irritated — with what they perceive as efforts to police their material and dictate what can or can’t be said.

Burr’s material picks on a wide range of targets, including Elon Musk. But he was recently confronted by NPR’s Terry Gross regarding his jokes directed at women, including the #MeToo Movement, the WNBA and feminism — or more to the point, the absurdity, in his eyes, of men referring to themselves as “male feminists.”

“See, this is where you lose me,” said Gross, referring to his anti-feminism. Burr retorted: “It does not surprise me that here, on this show, talking to a white woman, is where I lose you.

Comedy’s new wave is pro-Trump, but also pre-Trump

Reps for Gillis, Rife, Hinchcliffe and another transgressive comic, Tom Segura, declined to comment for this article. But they have found allies from others in the comedy world who might not share their ideology, such as Jon Stewart, who essentially defended Hinchcliffe’s dig at Puerto Rico, saying on “The Daily Show”:

“Obviously in retrospect, having a roast comedian come to a political rally a week before election day and roasting a key voting demographic, probably not the best decision by the campaign politically. But to be fair, the guy is really just doing what he does.”

Indeed, among comedians, the prevailing mindset has long been, as Seinfeld said in his initial remarks about “PC crap,” that it’s ultimately up to the audience to determine what’s funny. From that perspective, it’s perhaps not surprising that comics would rally around the notion of their contemporaries being unfettered in terms of saying what they want, even if they don’t necessarily support the sentiments expressed.

Although the current wave of conservative-leaning comics is heavily tied to Trump — on election night, UFC boss Dana White thanked Von and Joe Rogan for helping the GOP win — their brand of comedy is hardly new. 

“Comedy and what is acceptable and what isn’t acceptable, and what is mainstream and what is edgy and where is the line, all of these are constantly moving,” Federman told TheWrap. “This has been going on since the vaudeville days and even before that. That’s just the nature of this art form.”

“You can’t say [—-] anymore.”

Gillis was dinged in the past for using the word “retard,” which is sometimes referred to as “the R-word” since it’s deemed to be offensive, similar to “the N-word,” as a form of disparagement. He used the word freely in his 2023 Netflix special “Beautiful Dogs,” then half-apologized, saying, “My bad. I’m not trying to give myself a pass on being able to use that word.”

Gillis then turned that into a bit, saying, “I don’t know if you can tell by looking at me, but I do have family members with Down Syndrome,” before fondly talking about his Uncle Danny, who is always sneaking homemade grilled cheese sandwiches into restaurants.

Right-leaning media figures have embraced the new transgressive normal. “Gillis exposed the fraud of these cultural hall monitors by meticulously crafting his set to both lean into the controversy of his past and flip it on its head,” argued Steve Krakauer, an executive producer of the Megyn Kelly Show, offering a defense of Gillis in an opinion piece for The Hill.

Gillis is hardly the first comic to bring back the “R-word.” Tom Segura, who hosts the “Two Bears One Cave” podcast with fellow comedian Bert Kreischer, did a riff on the term in his 2018 special “Disgraceful.” “You can’t say retarded anymore,” he said. “People get very upset.” The crowd at the Paramount Theatre in Denver ate it up.

After Harvard Law professor Laurence Tribe, wrote, “I cannot recall encountering anything more hateful or painful than the stigma Segura has weaponized in the name of ‘comedy,'” Netflix chairman Reed Hastings defended Segura’s right to use the word.

“Even though many find Segura’s comments hurtful, in this instance they fall within the bounds of creative expression,” Hastings wrote in an email to Tribe.

Netflix has also defended what is perceived as anti-trans material by other, higher-profile comedians, including Dave Chappelle and Ricky Gervais, despite complaints —and even walkouts — from employees, saying the service caters to a wide variety of tastes.

Hastings added that “certain portions of any creative work including stand-up comedy can and do offend and are intended to evoke a range of responses,” adding that no one has to watch any particular show on Netflix.

Netflix CEO Ted Sarandos also defended working with both Hinchcliffe and Chappelle at a PaleyFest event in New York, picking up the mantra repeated by comedians in noting that stand-up is ultimately “defined by the audience. If the audience laughed, it worked … You can’t say, ‘That’s not funny’ if 18,000 people are laughing. You can say you disagree with it. You could say that it offends you. You can say that it hurts you. But you can’t say it’s not funny.”

“What am I going to do? Get canceled?”

In 2023, Matt Rife alienated his many female fans with a joke in his Netflix special “Natural Selection” about domestic violence. He then followed it up by referring anyone who was offended by the joke to a site selling helmets for people with special needs. 

After making a few transgender jokes at a subsequent show at the Hollywood Bowl, Rife quipped, “What am I going to do? Get canceled? Cool, I’ll do another Bowl show, awesome.” He added, “You know that’s not a real punishment … nothing happens. Prison’s a punishment.”

“I don’t really adhere to this whole sensitivity rumor in the comedy world that you can’t say anything anymore. That’s bulls–t. You can say whatever you want,” he told Variety in 2024.

In a recent appearance on “The View,” Rife said, “I don’t think anything is off-limits. The very thing you might think is off-limits — the thing that makes people uncomfortable — might be exactly what they need to heal. A loved one passing away, something that could be so emotionally devastating — there’s no cliché in saying that laughter is the best medicine.”

Federman, who penned the 2021 book “The History of Stand-Up: From Mark Twain to Dave Chappelle,” said what’s considered appropriate is always changing. “It used to be that swear words were absolutely taboo, until Lenny Bruce was like, ‘This is the way my jazz musician friends talk. This is the way I talk. Why can’t I bring this to the stage?’ Now no one blinks if you say the F-word. It’s not even a thing.”

He referenced a famous quote from late comedy legend George Carlin: “I think it’s the duty of the comedian to find out where the line is drawn and cross it deliberately.”

“Ultimately, you have to compete in the marketplace, and if enough people think you’re offensive and gross and not funny, then you won’t get booked, because there won’t be enough people going to your shows,” he said.

He added, “Shane Gillis is saying that word ‘retard,’ but it’s just part of an ongoing dance between audiences and performers, and as a performer, you eventually have to find out where that line is.”

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