The truth hurts for Donald Trump, especially when Bill Maher dishes it out

The US needs jesters to hold up a mirror to society, now more than ever

Back in 2013, I got a call from Bill Maher.

He was being hit with a lawsuit by Donald Trump and thought it would be “comedy gold” for my column. The host of HBO’s Real Time With Bill Maher had joked that Trump was the love child of a human woman and an orang-utan – what else could explain the tangerine hair? Maher offered to give $5 million to charity if he could see the birth certificate of Trump, who had offered $5 million to charity for records to verify the birthplace of President Barack Obama.

Trump failed to see the parody and thought the joke was mean. The flamboyant mogul told his lawyer to answer Maher with a letter: “Attached, hereto, is a copy of Mr. Trump’s birth certificate, demonstrating that he is the son of Fred Trump, not an orang-utan.” Then Trump sued Maher for $5 million before dropping the suit eight weeks later. (The Trump representative who threatened to refile the suit was none other than Michael Cohen.)

“He’s not even a real person,” an exasperated Maher told Conan O’Brien about Trump at the time. “He’s just like a pop reference from the ’80s.” It was like beefing with JR Ewing from Dallas, he said.


I told Maher that it wasn’t worth writing about Trump and his silly lawsuits and risible presidential aspirations.

“Forget it,” I said. “Trump doesn’t matter.”

Oh, well. Nobody gets it right all the time.

At 68, the comedian is still a thicket of thorns in Trump’s side. He led the pack in 2015, taking the threat of Trump seriously. He led again in 2020, warning that Trump would not accept the results if he lost. And he predicts the same this time if Trump loses again – two grooms showing up at the altar on January 20th (which happens to be Maher’s birthday).

“It’ll be disputed and it’ll be ugly,” he said over a recent dinner at Craig’s, a Los Angeles show business canteen.

Maher has fun comparing the heavily made-up Trump with a drag queen. After Trump’s team asked for a mistrial in the New York hush-money case, Maher japed that the former president’s drag name was “Miss Trial”.

The dumbest thing you can do in life, I think, is to have almost everything and then obsess on what you don’t have

—  Bill Maher

But the comedian is about more than one-liners these days. He has become our own time’s prickly, patriotic Will Rogers, drawing acclaim – and fire – for his yeasty interviews and his lacerating editorials at the end of Real Time,” taking on the right, the left, the media, romance, college campus protests, cancel culture, victim culture and technology gone awry.

His new book, What This Comedian Said Will Shock You, is the “crème de la crème”, as he says, of a decade’s worth of his editorials intended to “break through the bubbles”.

“If he sees hypocrisy, disingenuousness, cruelty or intellectual dishonesty, he calls it out,” said Richard Plepler, who worked with Maher as head of HBO and now heads Eden Productions at Apple TV. “We’re living in an environment where nobody seems willing to listen to anything but their own tribe, and Bill has this really preternatural ability to open up people’s ears so they maybe, God willing, learn something.”

Maher evokes the twin archetypes of the wisecracking kid who sat behind you in school and the grumpy uncle who sits next to you at Thanksgiving. He’s a rebel with a cause: He actually cares about the things he complains about, so there’s heart behind the cynicism.

Jerry Seinfeld called the consistently high level of Maher’s editorials “shocking”. “Your brain is worthy of all the attention it gets,” he teased Maher on Club Random, Maher’s podcast.

His range may be explained by something Maher, a Cornell history big, writes in his book: “I watch the History Channel like most guys watch Pornhub.”

He is not universally beloved. Some people find him smug; some think he has been red-pilled. His show has been nominated for an Emmy 21 times without a win.

“I am the love that dare not speak its name,” he said, laughing. “It’s almost ridiculous; I should have won 20!”

If it’s Trump against Biden, I will vote for Biden’s head in a jar of blue liquid

—  Bill Maher

Growing serious, he said that it no longer stings as much: “What I really have learned now is that, it is good being old when you’re smart in a way you weren’t when you were young. The dumbest thing you can do in life, I think, is to have almost everything and then obsess on what you don’t have.”

But even without a fistful of gold statuettes, he is undergoing what Katie Couric, a guest on Club Random, called a “Bill-aissance.”

He seems to make more news than all of the other night-owl comedians combined, no doubt because he breaks free of comedy’s congealed partisan worldview. Unlike most other political commentators, he does not pander to the left or the right.

“Let’s be honest,” he said. “The only thing that the two parties really have in common is that they’re both hoping their candidates die.”

Sometimes Fox (which he says he rarely watches) loves him and MSNBC is mad at him, and sometimes it’s the reverse. In a world awash in disinformation, Maher gives blunt, practical opinions, not filtered through ideology or likeability, on everything from Barbie to Bibi to babies – and why he never had them.

“Why can’t everybody live in my world, in the middle, where we’re not nuts?” he wondered, ordering a shot of tequila to go with his Margherita pizza. The dedicated health freak, opponent of treating obesity as body positivity, and Ozempic sceptic has a small bottle with a dropper, dripping into his sparkling water a product called Jing, a bubbly water enhancer with no aspartame, gluten or carbs.

Maher is constantly asked why he makes fun of the left more than he used to.

“Yes, I do, because they’re goofier and more obnoxious than they used to be,” he told his guests, Frank Bruno and Douglas Murray, on his show recently. “They also just became weirder.”

“I’m a comedian,” he told me. “I’m going to go where the ridiculous is.”

About the fans he has lost for not toeing the blue line, he writes in his book, “I do not miss them.”

He thinks the right is more dangerous, and he espouses “the Blue Liquid Doctrine”: “If it’s Trump against Biden, I will vote for Biden’s head in a jar of blue liquid.” But that’s not good enough for his liberal friends in Hollywood, who pester him to shut up about Biden’s age and gait. (Maher kids that Biden should lean in to it and say, “I walk like a toddler with a full diaper, but I believe in democracy.”)

He thinks we should stop acting as if we’re heading toward civil war and start talking to one another. He loves his stand-up gigs in red states.

“We have to see each other not as mortal enemies,” he writes, “but merely as roommates from hell.” (He has been in that “bad-roommate situation”, putting white tape through the middle of the apartment.)

At dinner, we talked about the eruption of anti-Semitism.

“It’s hard to get your head around the thought of people yelling ‘Death to America’ on American soil,” he said.

He is disgusted with progressive students who, he writes, cheer on Hamas to preside over a country with few constraints against sexual harassment, spousal rape, domestic violence, homophobia and child marriage.

He calls elite universities “the mouth of the river” from which nonsense flows, producing “American-hating hysterics devoid of knowledge. If they had any knowledge about the Middle East or what apartheid really means or genocide, would they be on the side of Hamas, really?”

In ancient courts, the jester could speak the truth to the king with impunity, like Shakespeare’s fools. But given safe spaces and trigger warnings, being a jester isn’t what it used to be.

“He survived his first cancellation,” said media duchess Tina Brown, “and now has become a warrior for the rest of us, absolutely refusing to be careful.”

I got to know Maher after his first cancellation, in 2002 – the literal one of his ABC show, Politically Incorrect.

Proving that a 90 per cent approval rating is a dangerous tonic, the Bush-Cheney White House decided after September 11th that it would brook no criticism. Ari Fleischer, the White House press secretary, haughtily dressed down Maher when he agreed with a guest that, while they were fiends, the 9/11 hijackers were not cowards.

Maher, and all Americans, Fleischer said, needed “to watch what they say.” ABC dropped Maher’s show.

I wrote a column pointing out that, especially when our country is a target, “we should not suppress the very thing that makes our foul enemies crazed with twisted envy – our heady and headache-inducing clash of ideas. We should dread a climate where the jobs of columnists and comedians are endangered by dissent.”

My idol is Jonathan Swift, so I think satirists – the other “Swifties” – should be given a wide berth. Sometimes they’ll miss the mark, sometimes they’ll be offensive. But we need our jesters to hold up a mirror to our society, now more than ever.

Maher was moved when his producers recently gave him a box that looked like an engagement ring box, with a ring on a chain symbolising his attachment to his fans.

“This is the relationship of my life,” Maher told me about his loyal audience. “Not that I really wanted kids to begin with, but I would have ignored them anyway if they were tugging on my pants because I had to rewrite this editorial.

“I think that’s a chip in your head that you’re born with: You either like babies or you like fur,” said Maher, a Peta board member. “I just love fur. I can watch humans suffering in a movie, but I cannot watch animals suffering in a movie. I can’t even watch King Kong or Godzilla or Planet of the Apes or Seabiscuit.”

He was brought up in New Jersey by a nurse and a radio broadcaster (and later editor). “I still have some tapes of him doing the top-of-the-hour news,” he said of his dad. “I have one the day Mickey Mantle retired.”

He was raised Roman Catholic before he was shocked by some news. “I was 13 when it came up at Christmas that my mother’s family side was Jewish,” he said.

“It never even entered my mind to ask why my mother never went to church with us,” he said. “It’s very strange when I look back on it, but back then, it was, ‘Don’t talk about politics or religion.’ Now it’s all we talk about. We’re always at each other’s throats because these are things you’re never going to really agree on.”

He is thinking of giving up stand-up after his next HBO special. “It’s like playing the cello,” he told me. “You got to always be working at it.”

On Club Random, where he gets stoned and sips tequila and invites guests to partake of pot or their drinks of choice as well (Seinfeld had coffee; Couric had a paloma), Maher can get downright sentimental, and confessional. He spoke to Martin Short about waking up in the middle of the night with morbid thoughts, by which he meant death. He fretted to Seinfeld that “men have been ruined by the phone and pornography. It’s rapey. It’s domineering. And this is what young men see.” The old days of Playboy, he said plaintively, have been replaced by “horrible things, choking and spanking”.

He has a stake, with John McEnroe, in Woody Harrelson’s Hollywood pot dispensary, the Woods, and recently hung out there with Paul McCartney. “I got to say, he was great,” Maher said.

He sleeps until he wakes up naturally, at about 11 am or noon; then he fasts most of the day because, he said, eating slows you down. “Three meals is just something somebody made up,” he said. “God didn’t put it on a tablet.” He takes his two rescue dogs, Chico, who has one eye and is about 15 years old, and Chula, 10, and shoots baskets and gets high and writes; about 3 pm, he has a shake with protein powder, yoghurt, pumpkin seed butter and chlorophyll, with avocado and tomato “because I was told Hispanic men have very low rates of prostate cancer”; and has a light meal at night.

As we left Craig’s, with Maher heading to his grey, all-electric Mercedes, I asked him if he ever feels as though he’s beating his head against the wall. He does. But, he said drily, he’s willing to tie himself to the mast and “keep sailing onward.”

“I don’t want to hate half the country,” he said. “I don’t hate half the country. And I don’t want America to get a divorce.”

This article originally appeared in The New York Times.