Patton Oswalt warns Bill Maher against appeasing Trump, says president ‘hates himself’

Maher recently tried to show openness and willingness to engage with Trump
Bill Maher calls out media fixation on Trump and says their in-person interaction was ‘gracious and measured' (Screenshot/RealTimewithBillMaher/Youtube, Photo by Frazer Harrison/Getty Images)
Bill Maher calls out media fixation on Trump and says their in-person interaction was ‘gracious and measured' (Screenshot/RealTimewithBillMaher/Youtube, Photo by Frazer Harrison/Getty Images)

LOS ANGELES, CALIFORNIA: Amid Bill Maher’s softening tone towards President Donald Trump, comedian Patton Oswalt appeared to school the Comedian and political commentator that appeasing Trump will only make him lose respect.

While Bill Maher remains Trump’s vocal critic, he has adopted a more pragmatic approach.

He has recently called out the media for its obsession with Trump and described his face-to-face interaction with the president as "gracious and measured."

Oswalt says Trump disrespects appeasers

During an appearance on The Dean Obeidallah Show, Dean Obeidallah compared Bill Maher’s recent outreach toward Donald Trump with the more confrontational approach taken by former The Late Show with Stephen Colbert host Stephen Colbert.

LOS ANGELES, CA - SEPTEMBER 18:  Comedian Patton Oswalt, winner of Best Writing for a Variety Specia
Comedian Patton Oswalt won the Best Writing for a Variety Special award for 'Patton Oswalt: Talking for Clapping' at the 68th Annual Primetime Emmy Awards on September 18, 2016, in Los Angeles (Photo by Frazer Harrison/Getty Images)

Patton Oswalt argued that trying to “placate” Trump does not work because, according to Oswalt, Trump quickly loses respect for people who flatter or appease him.

Speaking on The Dean Obeidallah Show, host Dean Obeidallah pointed to Bill Maher as an example, noting that the comedian had recently met Trump for dinner and initially made conciliatory remarks about the president before later becoming a target of Trump’s criticism again.

“And at first (Bill) is saying sort of nice things about Trump. And then Trump just turns on him anyway. Like you can’t win with him. I don’t know what people don’t get that lesson,” Obeidallah argued. Oswalt said Maher’s experience demonstrated why trying to “placate” Trump does not work.

“The reason that Trump is turning on Bill Maher is because Bill tried to, I’m sure with good intentions, tried to placate him and you can’t do that with him,” Oswalt said.

He contrasted Maher’s approach with late-night hosts such as Stephen Colbert and Jimmy Kimmel, who have remained openly critical of Trump.

President Donald Trump departs an event for NCAA national champions in the State Dining Room of the White House, Tuesday, April 21, 2026, in Washington. (AP Photo/Alex Brandon)
Trump departs an event for NCAA national champions in the State Dining Room of the White House, Tuesday, April 21, 2026, in Washington (AP Photo/Alex Brandon)

“By defying Trump, this is going to sound kind of weird, Colbert and Kimmel, yeah, Trump hates them but he hates them because they don’t love him. He wants them to love him,” the comedian added.

“And then the minute they love him, he has zero respect for them because deep down he hates himself.”

“And anyone, anyone who does business with Trump, you would just think basic greed would make you want to defy him. Because anyone that does business with him, you get destroyed,” Oswald suggested.

Trump–Maher feud: satire vs politics

Maher had long mocked Trump publicly, especially during the “birther” controversy, the false conspiracy theory pushed by Trump and others claiming Barack Obama was not born in the US.

In 2013, Maher jokingly said on-air that he would donate $5 million to charity if Trump could prove he was not “the son of an orangutan.” It was satire mocking Trump’s obsession with Obama’s birth certificate.

Maher acknowledged that Trump accomplished something many thought might be impossible. (screenshot,@BillMaher, X)
Maher recently tried to show openness and willingness to engage with Trump personally by having dinner with him at the White House (screenshot,@BillMaher, X)

Trump responded by filing a $5 million lawsuit against Maher, claiming breach of contract and defamation. The lawsuit was widely viewed as frivolous and was eventually dropped.

Maher recently tried to show openness and willingness to engage with Trump personally by having dinner with him at the White House.

GET BREAKING U.S. NEWS & POLITICAL UPDATES
STRAIGHT TO YOUR INBOX.

MORE STORIES

Brian Stelter said removing major news outlets from the regular press rotation could create practical problems for covering Trump
23 hours ago
The court filing comes amid a separate dispute over Jimmy Kimmel’s interview with Texas Senate candidate James Talarico
2 days ago
Joy Behar criticized Donald Trump Jr after he confirmed Russian businessman Umar Kremlev helped fund his wedding, calling it a 'generous gift'
4 days ago
Maria Bartiromo's future became a subject of speculation almost immediately after Fox News announced her departure on September 3
Sep 10, 2026
Kimmel said the FCC had threatened him, his show, and ABC over 'simple, traditional editorial decisions, guest bookings it would seem they don’t like'
Sep 10, 2026
Whoopi Goldberg invoked Barbara Walters’ original vision for the talk show, urging viewers to engage with guests despite political differences
Sep 10, 2026
Reflecting on the concerns he had a decade or more ago, Jimmy Kimmel said many of them now seem insignificant in hindsight
Sep 5, 2026
The timing of Maria Bartiromo's exit quickly prompted questions about a potential role in the Trump administration
Sep 3, 2026
Carlson questioned why no effort was already underway to remove Trump, saying anyone who tolerated such discussions would be 'by definition unfit'
Aug 30, 2026
Dolly Parton’s death drew tributes from Miley Cyrus, Taylor Swift, Beyoncé, Sabrina Carpenter, Trump, Barack Obama, and Bill Clinton
Aug 29, 2026