Comics like Tim Dillon helped Trump reach young men. Democrats want in on the joke

Digital creators like Tim Dillon have emerged as a key force behind Trump’s victory. (Netflix)

American Comedian Tim Dillon isn’t expecting a certain member of the British royal family to stream his newly released stand-up special on Netflix.

And he thinks the same logic should apply to Democrats who may fault him and other entertainers for U.S. President Donald Trump’s return to power.

“You can’t go to war with straight white men for four years and then ask why they didn’t vote for you,” Dillon told CNN. “That seems crazy. I’ve made fun of Meghan Markle a lot. I can’t then go, ‘Why don’t you think Meghan Markle is watching (my special)?’ I just think you have to pick your fights in a better way.”

As with much of Dillon’s commentary, the provocation was delivered in the style of a punchline — but with a point that matters for both political parties as well as the fast-changing media landscape.

Digital creators like Dillon — irreverent, predominately male and previously politically unclassifiable — emerged as a key force behind Trump’s victory. Democrats and Republicans alike have credited these podcasters, YouTubers and self-styled contrarians for driving support for Trump among men, particularly those under 40.

It’s not yet clear if the dynamic will hold. Democrats say they’re already adapting to address corners of the Internet they have long overlooked, and Republicans concede Trump’s singular celebrity may prove challenging to replicate. Within the entertainment industry, opinions are mixed on how this new wave of influencers will wield their clout going forward.

Some have pulled back from partisan politics in the wake of the election while other influential figures, like Barstool’s Dave Portnoy, have selectively criticized Trump’s performance so far.

Regardless of how the two parties proceed, Dillon predicted: “You’re going to see a lot more attention being paid to the Internet.”

‘It was kind of fortuitous'

Dillon, 40, stands near the center of the political transformation that is taking place. Though openly gay and a resident of deeply blue Los Angeles, he has few allegiances and for years his barbs mocked cultural and political establishments across the spectrum. But as the election neared, his critiques of Democrats, voiced weekly in his long-running podcast, grew increasingly acerbic. Then, less than two weeks before Election Day, he released an 83-minute interview with Trump’s running mate JD Vance – an improbable booking that remains surreal, if not absurd, even to Dillon.

“It was actually the goal and why I started comedy — JD Vance,” Dillon said with his characteristically dry delivery. “I knew about him when I started out in 2010 and I had it all plotted out like ‘A Beautiful Mind’ on the wall.”

Then, more seriously: “It was kind of fortuitous. We just have this podcast that’s big and people listen to it.”

The elevation of comedians as political influencers has been years in the making. Stand-up comics have become some of the country’s most recognizable and highest-paid celebrities. The top 10 comedy acts of 2024 grossed nearly US$400 million in tickets, up 52 percent from the year before, according to Billboard. Americans spent tens of millions of hours watching their specials on Netflix and other streaming services. Dillon’s latest release, “I am Your Mother,” rose to Netflix’s coveted Top 10 most-watched list after debuting on Tuesday.

The Trump campaign, more than that of Democratic nominee Kamala Harris, appeared attuned to that reality. From sit-downs with Dillon and the comedian Theo Von to appearances with the online pranksters known as the Nelk Boys, podcaster Joe Rogan and Twitch streamer Adin Ross, Trump’s team placed calculated bets on an ecosystem of influencers who may not be conventionally political but command attention — and, more crucially, loyalty — from the digital generation.

“Trump understands the two cultural forces that I’ve seen in my lifetime that have changed the way people have behaved: reality television and social media,” Dillon said. “He understands social media and using it to communicate. Now that we have phones, we’re all starring in our own reality television shows. He understands that, and he was able to utilize that understanding to connect with people in a way that Kamala didn’t seem to understand. I felt like he just had the upper hand.”

Democrats play catch up

A post-election review of the digital landscape by the progressive media watchdog Media Matters found right-leaning online content has five times as many followers as programs on the left. Former Daily Show Host Trevor Noah is the only left-of-center voice among the top 10 most popular internet shows, the analysis said.

“The Democratic Party lost control of the cultural zeitgeist and the ways in which culture is formed,” said Rob Flaherty, the deputy campaign manager and digital chief for former Vice President Harris. “What you ended up with is an online environment where all the fervor is on the right, and all the people in the middle are seeing is that fervor.”

For his part, Dillon downplayed his role in Trump’s victory, and he isn’t alone in doing so. Comedian Andrew Schulz, for example, recently asserted that Trump’s appearance last year on his popular “Flagrant” podcast made the Republican’s supporters “feel more comfortable voicing how they were already going to vote” but didn’t alter their ballot.

“Maybe in those situations, he feels a little less radioactive,” Schulz told the Los Angeles Times.

The Trump campaign, though, certainly saw value in these appearances (Trump once appeared three hours late for a campaign event so he could tape his interview with Rogan). Democrats also clearly disagree with Schulz and are now making a push to match the right’s digital dominance.

The Democratic National Committee recently announced plans to overhaul its online communications. Already, the party’s potential 2028 contenders have made early attempts to mimic Trump’s success. California Gov. Gavin Newsom and Kentucky Gov. Andy Beshears launched competing podcasts. Michigan Gov. Gretchen Whitmner recently gabbed on a Detroit Pistons basketball podcast while Pennsylvania Gov. Josh Shapiro talked Philadelphia Eagles and Trump with outspoken ESPN commentator Stephen A. Smith earlier this year.

Within the Democratic Party, some have begun to explore how to build a podcast ecosystem to rival the MAGA-friendly manosphere. More simply, some say what the party really needs is its own Joe Rogan.

Already, though, Democrats have confronted the challenges of neutralizing the right’s digital advantage. A person close to Harris’ campaign said several popular online shows turned down offers to interview the Democratic nominee, including Hot Ones and podcasts hosted by the Ringer’s Bill Simmons and former NFL stars Travis and Jason Kelce, for fear of alienating Trump supporters in their audience.

“Voters are attuned to when candidates are inauthentic and in 2025 there are very few Democrats who could go in there and hold their own because it’s a different part of the internet that Democrats have not lived in,” said Ammar Moussa, a Democratic strategist who oversaw rapid response for the Harris campaign. “I don’t think our solution to winning elections is as simple as finding a candidate who can go on the Nelk boys. There are larger issues. But how many Dem operatives are regularly listening to Joe Rogan or Andrew Schlutz or even know who the Nelk boys are?”

Dillon is quick to point out that he also extended an invitation to Vance’s Democratic counterpart, Minnesota Gov. Tim Walz. Rogan, Schulz and Von have publicly said they offered Harris interviews as well. Harris instead sat down with Alex Cooper’s sex-positive show “Call Her Daddy” and “All the Smoke,” hosted by former NBA stars Matt Barnes and Stephen Jackson, but mostly focused on rallies and high-stakes television appearances during her short three-month campaign.

“I don’t do many interviews, but none of them are super contentious,” Dillon said. “They’re all just kind of a conversation. So I don’t think I would have been disrespectful in any way.”

But as he eviscerated the Democratic playbook, identity politics and the country’s costal elites, Dillon acknowledged why the Harris campaign may have avoided him.

“Yeah, I mean, I think I agree with Vance more than I do with Tim Walz.”

As for his interview with Vance, Dillon said he wished he had pressed the Republican on the outsized influence of tech giants like billionaire Elon Musk in Trump’s orbit, which he has since criticized on his show. Dillon has also been bothered by the administration’s crackdown on foreign college students involved in campus protests against Israel.

“I’m a free speech guy. I don’t love that,” Dillon said. “We always talk about these antisemitic conspiracy theories that run rampant. They’re all over the place. I think a great way to feed those theories are things like this — deporting people that have been critical of Israel.”

Beyond 2024

Alex Bruesewitz, a Trump adviser heavily involved in the campaign’s digital strategy, said their approach was simply to find the online shows with the largest audiences outside of conservative media. Initially working off a list of potential podcasts recommended by Ultimate Fighting Championship CEO Dana White, the campaign ultimately fielded suggestions from the president’s children or other influencers who interviewed Trump.

After each appearance, Bruesewitz, a 28-year-old who served as Trump’s Gen Z whisperer and as a liaison between the campaign and online creators, would print out the metrics for Trump to review. “He loved the ratings, and when you showed him that, he would want to do more,” Bruesewitz said.

“It’s not something I would recommend for all politicians, but they’re going to start doing it anyway,” he added.

What remains to be seen is how these influencers respond as the political world reacts to Trump’s successful playbook. One person involved in the entertainment industry called the months since the election a “dissection period” where many comedians are anticipating a surge of invitations and requests from ambitious politicians but are still weighing how much they care to engage, if at all.

For online creators, there may be limited audience payoff in serving as the new political gatekeepers. For instance, Shapiro’s appearance on Steven A. Smith’s podcast drew just 27,000 views on YouTube — a figure dwarfed by subsequent interviews in the last month with billionaire businessman Mark Cuban and conservative commentator Ben Shapiro.

“The entertainment business wants to make money,” Dillon said. “It doesn’t exist to teach people lessons. That’s not why it was invented. There was a belief after Trump was elected the first time that the job of the entertainment business was to act as a resistance to Trump, and it proved pretty ineffective. I think what it should be doing is entertaining people. I think that’s what it’s going to get back to doing. I don’t think it’s going to effectively marshal any type of political capital.”

In his latest Netflix special — which also cracked the streaming service’s Top 10 list — Andrew Schulz made no mention of the presidential race where he briefly held a starring role. But his online show recently hosted Chamath Palihapitiya, the billionaire investor and “All-In” podcast host who has emerged as staunch defender of Trump’s tariff policies.

Since speaking to Trump and Vance last year, Von has mostly interviewed other comedians and entertainers, though he did release a two-hour episode with right-wing commentator Candace Owens. Dillon’s weekly show has largely reverted to hour-long monologues, aside from a conversation with Steve Bannon, the populist strategist and former Trump adviser.

Conventional Republican figures, so far, have had less luck breaking into these spaces than Trump, even amid a continued dalliance with the alt-right.

“A lot of politicians have come up to me asking me to help them get on the podcast circuit,” said Bruesewitz, “And you have to tell them, ‘They don’t really want to talk to you.’”

For now, that’s Dillon’s position. While he’s open to inviting presidential contenders or their running mates on his show down the line, he isn’t interested in vetting them for America along the way.

“I find everyone really boring, and the only person I really am interested in hearing from is myself,” Dillon said. “That’s why my show is fun for me to do – because I just say my opinion.”

Article by Steve Contorno.