When Larry Wilmore welcomed controversial right-wing commentator Ben Shapiro on his podcast last year, his fans revolted. The former host of The Nightly Show wasn’t fazed.
“I’m like, whatever everybody, calm down,” Wilmore says on this week’s episode of The Last Laugh podcast.
For Wilmore, Shapiro is a “fire-thrower” in “the same way that people on the left are fire-throwers.” He knew that “a lot of people would disagree with Ben and I thought that was the point to have him on, to have that conversation.”
“And he’s not the person that people ascribe him to be,” Wilmore adds. “He really isn’t. He’s really a nice guy. I just happen to disagree with a lot of what he says.”
There is plenty for Wilmore to disagree with, on both a personal and political level.
Four years ago, Shapiro wrote that President Obama was a “disgrace” for saying he “appreciated” the way Wilmore closed out his White House Correspondents’ Dinner speech. More recently, Shapiro expressed shock and dismay that The New York Times’ Nikole Hannah-Jones had received a Pulitzer Prize for commentary for The 1619 Project.
Wilmore is aware that equating Shapiro with the loudest voices on the left will lead critics to accuse him of taking a “both sides” approach. “There are so many people out there who hate ‘both sides’ types of arguments,” he says. But by nature, he says he likes to look at both sides of any divisive issue.
Take the debate over stay-at-home orders versus reopening the country in the face of the coronavirus pandemic. “We are in a classic both sides situation right now,” Wilmore says. “There is complete legitimacy to people who want to reopen the economy. There are so many small businesses that are hurting or people who, every day not working is a blow—let alone a week, let alone a month, let alone months. It’s devastating.”
On the other side, “there’s the concern about the health of society and people dying.” He’s horrified by “the way that it can take someone out so fast.”
That’s why Wilmore likes to listen to arguments from the “other side,” including conservative pundits like Shapiro, who also hosted him on his popular podcast last year. “I call it the ‘other side’ only because I’m mainly associated with the left,” Wilmore says. “But I’m more in the middle, to be honest with you.” He likes to “see how people are framing issues” and then form his own opinions based on those various arguments. He calls himself a “passionate centrist” because “half the time I disagree with myself.”
“It’s true,” Wilmore says. “Many times I’ll go down a road and I’ll see an argument and go, ‘Oh, I’ve never looked at it like that.’”
That said, Wilmore says Shapiro was not able to change his mind about anything during their two conversations. “I wanted other people to hear these arguments from the other side, so I was really doing it for the sake of my audience,” he says, even if they didn’t seem to appreciate it. “I actually want to have more of those types of conversations on my podcast with people who I might disagree with. Or people who have different perspectives. It’s just good to get outside of your own bubble.”
“If a lot of people are going in this one direction, I have to go in the other direction,” he says. “I’m contrary by nature.”
That’s a sentiment that is regularly expressed by comedians who are at their best when they are able to surprise audiences with unexpected points of view. Simply telling audiences what they want to hear rarely produces the funniest result.
Michelle Wolf, another Daily Show alum who delivered a controversial set at the White House Correspondents’ Dinner, lamented to me last fall that people “just assumed” she was a political comic after she was tapped for that gig. “And it’s a weird thing to make an assumption about, because I was hired to do a job; a job I’m still very proud of,” she said. “But I can write jokes about any subject. You give me a subject and a half-hour, I’ll give you 10 jokes.”
“I am not a raging liberal,” Wilmore adds. “When I rail against Trump, it’s not from a leftist standpoint, really.” When he was hosting The Nightly Show, he says a lot of the positions he staked out “happened to be” associated with the left, such as advocating for “underdogs” like women and minorities. “But it doesn’t mean that I’m an activist for that,” he says. “I can be an advocate without being an activist. If it’s an underdog, I’m always going to try to be an advocate for that. My opinion doesn’t matter as much as the truth of the issue.”
As an example, he points to another “divisive” issue like abortion, on which he personally takes a more “centrist” view but has advocated on the left. “I’m Catholic, I understand the ‘life’ position,” he says. “I understand it from a moral point of view, from a religious point of view. But as a political argument, I have to be on the left side, on the choice side. I have no choice. Because there’s a more compelling argument politically for the left side of the argument. Privately, it’s completely different. But that’s kind of the point of choice, too.”
There’s one right-wing pundit, however, who Wilmore just could not abide.
During the “Overtime” segment of a 2017 episode of Real Time with Bill Maher, Wilmore found himself seated at the same table as Milo Yiannopoulos. In an earlier one-on-one interview, Maher essentially ceded the stage to the infamous alt-right troll, giving him a platform to spout his hateful rhetoric more or less unchallenged.
After Yiannopoulos called him “stupid” to his face, Wilmore said what Maher wouldn’t, straight-up telling him, “Go fuck yourself.”
“I experienced it a little differently from the way people took it,” Wilmore says now. “For me, I wasn’t there trying to do something that Bill wasn’t doing. I was reacting more directly. He was insulting me and Malcolm Nance, who’s this brilliant guy. And calling us stupid, basically.”
“I was like, I’m a grown-ass man, who the fuck do you think you’re speaking to?” he recalls. “I don’t care who you are. Who do you think you’re talking to? Like I’m not going to come back at that? Of course I’m going to come back at you. What is wrong with you? So I think he was kind of surprised by that too.”
Next week on The Last Laugh podcast: Comedian and Silicon Valley star Jimmy O. Yang, whose new stand-up special Good Deal premieres on Amazon this week.
