Michael Ian Black on the Best Way to Defeat ‘Humorless’ Trump

Michael Ian Black began his career performing deeply absurdist comedy with his legendary sketch group The State and the besuited comedy trio Stella. Now, among other things, he’s a weekly columnist covering the 2024 election for the Daily Beast. But Black does not consider himself to be a political commentator “in any way, shape or form, even though I often comment on politics,” he says in this week’s episode of The Last Laugh podcast.

During our wide-ranging conversation, Black shares his thoughts on where the 2024 race stands right now, how Donald Trump became America’s worst crowd work comedian, why he’s cautiously optimistic about the prospect of a Kamala Harris presidency, and what viewers can expect from his new satirical CNN game show Have I Got News for You with Roy Wood Jr. and Amber Ruffin. Plus, what he remembers about filming his explicit sex scene with Bradley Cooper in Wet Hot American Summer and why, after two reboots on Netflix, the cult classic finally “feels like it’s done” to him.

We’re speaking ahead of the first (and only?) big debate between Harris and Trump and Black is loath to make any bold predictions about how it would play out. “In my short career as a quote, unquote political commentator, I have already made one of the single worst predictions of the campaign season,” he concedes, referring to a column posted the day before the game-changing Biden-Trump debate in which he wrote, “Whose mind is getting changed by watching 90 minutes of this bullshit? It’s a rhetorical question but I’ll answer, anyway: nobody.”

“Boy howdy, was I wrong about that!” he jokes now. So while he’s “hesitant” to make any debate predictions, he did posit that there’s a “pretty good chance Kamala will make Trump look fairly impotent” while also acknowledging that “there are times when she’s not the best extemporaneous speaker, and it’s entirely possible we’ll get one of those nights.” Ultimately, he concludes, “It could end up being decisive, it could end up being a nothingburger, I have no idea.”

Like many of us, Black has been thinking deeply about Donald Trump’s character for close to a decade, beginning with a satirical children’s book he published in 2016 titled A Child’s First Book of Trump. In May of that year, he joked to me that he was rooting for Trump to win the presidency because it might help his book sales. He wasn’t taking Trump seriously then, and he’s still not.

“The thesis of that book is that the way you defeat Trump and his ilk is to essentially ignore them, mock them, tease them,” he says now. “Because Trump is humorless, one of the most effective ways of dealing with him is with humor. He only knows humor as cruelty, he only knows how to mock and deride so if you can treat him the way the Harris campaign is, essentially a clown, as a buffoon, as somebody who should not be taken seriously, that can be pretty effective.”

In one of his recent columns for the Daily Beast, Black compared Trump to a “hacky” comedian, “trotting out all his tired bits from yesteryear to increasingly little effect.”

“His speeches have now devolved into what is essentially hacky crowd work,” he elaborates to me. “So he’ll have a speech on the teleprompter, and he’ll read a line or two of it, and then he’ll digress into Hannibal Lecter or sharks or making snide remarks about somebody or whatever, and then he’ll return to the speech for a line or two and then digress for half an hour. It’s like the worst crowd work special I’ve ever seen.”

As Black puts it, “He’s just saying whatever f—ing thing comes into his stupid mouth and spitting it out. That’s annoying when your friend does it. It’s super annoying when it’s the guy who wants to be president of the United States.”

If that type of rhetoric feels a bit harsh for CNN, where Black will be making jokes about the news on his new show with fellow comedians Wood and Ruffin starting this Saturday night, Sept. 14 at 9 p.m., he too was concerned that the cable news network might not willing to “go there” satirically.

“The very first conversation I had with CNN after I was offered the job was about this exact topic,” he reveals. “And they were very clear with me. They were like, ‘Look, go for it, go as far as you want to go, we’re totally game for this.’ Now, we’ll see once we get the thing on the air whether they really mean that, but so far, they seem totally happy to have us just make fun of anybody and everybody.”

He then jokes, “Including Jake Tapper, who’s going to get a real pie in the face from me!”

As for what comes next in his career after the election, Black says, “I don’t anticipate any return to the Wet Hot American Summer universe, at least with this cast. It’s possible you could do it with another cast and maybe have cameos by us, but I don’t think there’s any real appetite for it.”

Unless his lifelong comedy collaborators David Wain and Michael Showalter “think of some amazing take on it,” Black says, “It feels like it’s done to me. But, you know, as I said, I’m terrible at predicting things.”

Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, Google, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.