On ‘Real Time,’ Maher mocked the post and defended the dinners
President Trump and comedian Bill Maher are still trading insults roughly two weeks after sharing dinner at the White House. Trump posted a 1,300-word attack on Truth Social — his longest post ever on the platform, according to The Wall Street Journal — and Maher answered on Friday night’s episode of HBO’s “Real Time,” telling his audience that Trump “went off on me like Kelly Clarkson in a toy store.”
The dinner came in mid-October and included ESPN’s Stephen A. Smith and the musician Kid Rock. Chicken, mac and cheese and broccoli were served, Smith told ABC’s “The View.” It was the second time Maher had dined with the president in the past two years. The guests discussed topics such as Smith’s belief in the importance of historically Black colleges and universities, which Smith argued were being financially harmed by the administration’s actions against diversity, equity and inclusion. Maher, a critic of the president, challenged Trump on topics including the execution of the Iran war.
Kid Rock, the Detroit singer and a longtime Trump ally, told Fox News that he orchestrated the gathering. The dinner prompted Trump to say Maher “likes me a lot more than people understand.”
The pleasantries were short-lived. On the Oct. 23 episode of his show, Maher anticipated the criticism. “Yeah, I did it again, bitches,” he said. “F— you. I like these dinners.” In his monologue that night, he praised the gathering but jabbed at the president over his low approval ratings and his comments on Ohio Sen. Jon Husted’s physique.
The jabs were enough to trigger Trump’s longest-ever Truth Social post. It called Maher a “complete and total loser” and a “biased, dumb SLEAZEBAG” while attacking what Trump described as the comedian’s “Low Ratings.”
Maher had more material on Friday. Borrowing from President Obama’s recent joke that the White House now looks like a Cheesecake Factory opened by Saddam Hussein, Maher told his audience: “Dining at the White House is the opposite of the Cheesecake Factory. After you leave, they review you.”
The exchange is, according to the Journal, the latest and most visible example of the political balancing act Maher has walked for years as one of HBO’s longest-serving personalities. A self-described old-school liberal, Maher has reserved much of his scorn for conservatives but holds little patience for what he calls speech-policing and identity politics on the left. As progressive politics gained influence within the Democratic Party, he turned more of his barbs on the left, saying on his show and in interviews that he has not changed his political views so much as the party has moved away from him.
His defenses of Israel and criticism of Islamic fundamentalism have made him persona non grata among many progressive activists and something of a hero to conservatives who cheer his critiques of the progressive left, the Journal reported; Fox News frequently airs clips of him skewering Democrats. But while his stances alienate some fellow liberals, he continues to take aim at Trump and much of the Republican agenda.
“He is in his happy place when he is being attacked by the left,” said Matt Welch, editor at large at the libertarian Reason magazine and a recurring “Real Time” guest. “Attacked by the left and Donald Trump in the same week? Perfect.”
Maher’s weekly show, now more than two decades old, has averaged 3.3 million viewers per episode across HBO and the streaming platform HBO Max over the past two years, according to Nielsen. His recent guests span the political map: former White House press secretary Karoline Leavitt appeared last week, and Vice President JD Vance appeared in June. California Gov. Gavin Newsom and Pennsylvania Gov. Josh Shapiro have each appeared multiple times, and Vermont Sen. Bernie Sanders is a frequent guest.
Maher, who declined to be interviewed for the Journal’s article, has defended his willingness to engage with Trump supporters. “I don’t give them a free pass,” he told the Journal last year.
Maher and Trump have tussled before. Trump sued Maher in 2013 over a joke Maher made on “The Tonight Show with Jay Leno” challenging Trump to prove he was not the son of an orangutan; the suit was withdrawn. A stand-up comedian and occasional actor before finding his niche as a political provocateur with the 1993 launch of “Politically Incorrect,” Maher has spent much of his career alienating people across the political spectrum, the Journal reported. Shortly after the Sept. 11, 2001, terrorist attacks, he drew backlash for comments calling the hijackers “not cowardly.” ABC canceled the show the following year.
An unapologetic bachelor who enjoys a drink and a joint, Maher was a longtime fixture at Hugh Hefner’s Playboy Mansion parties, according to the Journal. In his act, he has delighted in skewering organized religion and traditional family life.
After Maher’s first dinner with Trump, in March 2025, “Curb Your Enthusiasm” creator Larry David wrote a satirical column in the New York Times titled “My Dinner with Adolf” — a thinly veiled rebuke of Maher’s efforts to find common ground with the president, as the Journal described it. “It’s like watching Lucy and Charlie Brown with the football, but I can’t decide who is Lucy and who is Charlie Brown,” said tech journalist and frequent “Real Time” guest Kara Swisher.