Michael Douglas Tells Bill Maher He Golfed With Trump: 'He Was a Funny Guy'

Michael Douglas has known Donald Trump longer than most of Washington has. Asked on Bill Maher's podcast whether he had ever met the president, he didn't hesitate: "Oh, sure. I played golf with him. He was at my birthday."

That exchange comes from the new episode of Club Random, posted Monday, and it was taped at an interesting moment. "You know I'm having dinner with him next week?" Maher told his guest. "At the White House, again."

Maher, for his part, made an admission about the last decade of Trump panic:

So the conversation is a preview of sorts: one of Hollywood's most famous liberals and the comedian about to sit at Trump's table a second time, trying to square the man they have met with the president they criticize.

The Trump Douglas knew

Douglas's Trump is a New York figure, not a cable-news villain. "No, I've known him in New York. You know, he was a funny guy, sort of a self-deprecating sense of humor," he said.

His worry is about what he sees now, and he was careful about how he put it. The Trump he knew in New York, Douglas said, had "nothing about this sort of fascist ... mentality." It is a contrast, not a label, and he followed it with the complaint he seems to care about most: "I don't want the unpredictability."

Then he went bigger. "I was born in 1944, and this is the worst time I can remember in my lifetime, not just the States, but just worldwide."

He also had an idea for making it better. In the coming Ukraine negotiations, he asked, "why doesn't Zelensky suggest, and the president could make it happen, that Russia and the United States dramatically reduce the number of nuclear weapons?" Then he made a promise: "And if President Trump can pull this off, I promise you he would be getting the Nobel Peace Prize."

Maher, before the second dinner

Maher, characteristically, argued with himself. Looking back on a decade of liberal panic over Trump, he said: "Let's be honest, our lives are good. It looked like he didn't f***ing end the world. A little of it was hysterical, but it's, you know, for good reason, you know, he is a maniac who does fascistic things and pals around with, likes dictators and, you know, that kind of s***."

It is the Maher formula in one breath: concede the overreaction, then keep the criticism. He has never pretended to be on the other team. "I've never voted Republican in my life," he told Douglas, before needling his own side. "I always say to my woke friends about the last election, we voted for the same person, okay? You're just why she lost."

The first dinner cost him at home. His sister, he said, keeps MSNBC on all day and is a "dyed-in-the-wool Democrat," and after the visit "she just really didn't want to talk to me." His plea was modest: "Could we just, you know, give one minute of time to, it's a little impressive that your brother is at a private dinner with the president of the United States."

Two dinners, one honest report

That first dinner, arranged by Kid Rock, took place in March 2025 (Variety). In April, Maher gave his HBO audience a full account: "Trump was gracious and measured," he said. "I'm just reporting exactly what I saw over 2 1/2 hours. I went into the mine and that's what's down there" (Forbes).

The second dinner happened on Oct. 15, the week after the taping: a four-hour evening with Kid Rock and ESPN's Stephen A. Smith that ran from the Oval Office to the unfinished ballroom (The Independent). Smith said Trump "didn't run from any questions." Trump told reporters, "Bill Maher — I will tell you what. He likes me a lot more than people understand, and I actually like him" (The Hill).

The father who watched Maher

The episode's warmest moment had nothing to do with politics. Douglas recalled what his father, the Spartacus star Kirk Douglas, watched right at the very end. "My father, my father, right at the very end, the only thing that he watched was Ultimate Fighting and Bill," he said. "He was 102 years old." He told Maher a version of the same story on Real Time in 2024 (Variety).

Cage fights and Bill Maher make an odd double feature, and maybe that is the point. Both reward people who can take a hit and keep talking.

That is rarer than it should be in 2026. A comedian who never voted Republican keeps accepting the president's invitations and reporting what he sees. A lifelong liberal who golfed with Trump still remembers him as funny. Neither has changed sides. They have just kept the line open, which is more than most of the country manages.