The latest dinner between Bill Maher and President Trump was two weeks ago, but insults are still being served.

On Friday night’s episode of HBO’s “Real Time,” Maher returned fire following the president’s 1,300-word social media rant against the comedian and political commentator, saying Trump “went off on me like Kelly Clarkson in a toy store.”He also borrowed from President Obama’s recent crack that the White House now looks like a Cheesecake Factory opened by Saddam Hussein. “Dining at the White House is the opposite of the Cheesecake Factory,” Maher said.

“After you leave, they review you.”The latest back and forth between Trump and Maher stemmed from a mid-October White House dinner with ESPN’s Stephen A. Smith and musician Kid Rock. Chicken, mac and cheese and broccoli were served, Smith told ABC’s “The View.”

It was the second time Maher dined with the president within the last two years. The unlikely dinner guests discussed topics such as Smith’s belief in the importance of historically Black colleges and universities, which he 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. Just days later, despite the in-person pleasantries, Maher and Trump soon returned to their old routines.

While the comic praised the gathering in his Oct. 23 monologue on his show, he jabbed at the president for his low approval ratings and comments on Ohio Sen. Jon Husted’s physique. That was enough to trigger Trump’s longest-ever Truth Social post, calling Maher a “complete and total loser” and a “biased, dumb SLEAZEBAG,” while also attacking what he described as “Low Ratings.”

Maher’s private tête-à-têtes with Trump, and the inevitable resulting attacks from the left and the president himself, are 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, he’s reserved much of his scorn for conservatives but also holds little patience for what he calls speech-policing and identity politics on the other side. As progressive politics gained influence within the Democratic Party, Maher increasingly turned his barbs on the left. On his show and in interviews, he has said he hasn’t changed his political views so much as the Democratic 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. Maher has become something of a hero to conservatives who cheer his critiques of the progressive left. Fox News frequently airs clips of him skewering Democrats.

But while his stances alienate some fellow liberals, Maher 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.”

His weekly show, now more than two decades old, has averaged 3.3 million viewers per episode across HBO and streaming platform HBO Max over the past two years, according to Nielsen. In recent years, many prominent conservatives and Trump supporters have appeared on “Real Time.”

Last week, Maher hosted former White House press secretary Karoline Leavitt, while Vice President JD Vance appeared in June. But “Real Time” remains a pit stop for Democrats as well.

California Gov. Gavin Newsom and Pennsylvania Gov. Josh Shapiro have both appeared multiple times, while Sen. Bernie Sanders of Vermont is a frequent guest. Maher, who declined to be interviewed for this article, has defended his willingness to engage with Trump supporters.

“I don’t give them a free pass,” he told The Wall Street Journal last year.

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 Trump.

“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 in an interview. 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. Shortly after the Sept. 11, 2001, terrorist attacks, he drew backlash for comments in which he called 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. In his act, he has delighted in skewering organized religion and traditional family life.

tory of tussles with Trump is extensive. Trump sued Maher in 2013 over a joke he made on “The Tonight Show with Jay Leno” challenging Trump to prove he wasn’t the son of an orangutan. The suit was withdrawn.

The latest gathering was orchestrated by Kid Rock, the Detroit singer and longtime Trump ally told Fox News. The dinner prompted Trump to say Maher “likes me a lot more than people understand.”

On last week’s “Real Time,” following his second dinner with Trump, Maher anticipated more criticism. “Yeah, I did it again, bitches,” he said. “F— you. I like these dinners.”