Patton Oswalt has one piece of advice for hosts caught up in President Donald Trump’s ongoing battle against late-night TV: Never give in.
“The most obvious lesson is: if you kowtow to Trump, he hates you,” Oswalt, 57, who just debuted a new comedy special, Tea & Scotch, told Obsessed: The Podcast. “If you don’t kowtow to him, he might still hate you, but he’ll respect you, and other people will respect you, and you will have a career going forward.”
“Think of all of the entertainers that have kowtowed to him, and have any of them benefited from that? Has there been any benefit?” he posited. “Does Trump have anyone’s back when the chips are down? Does he have anyone’s back? He has no one’s back. No one.”
“And he has said that. He’s openly said that,” Oswalt said, referencing Trump’s remark that he doesn’t “think about Americans’ financial situation.”
In March 2025, Real Time host Bill Maher joined Trump, 79, for a dinner at the White House, after which he said the president was “gracious” and “measured,” in contrast to his public persona. In response, Trump fired off an incendiary Truth Social rant where he called the late-night host a “highly overrated LIGHTWEIGHT” who suffers from a “severe case of Trump Derangement Syndrome.”
Maher, 70, caught strife from his fellow comedians—especially Larry David, who mocked the affair with a parody essay about a fictional dinner with Adolf Hitler—and Oswalt think he was deeply misguided in his attempts to cozy up to Trump.
“Bill Maher, with probably some pretty noble intentions, was like, ‘I’m gonna try to reach out and build a bridge to this guy,’” Oswalt explained. “And what he doesn’t understand is that—now I think he does understand—Donald Trump was raised like an abused shelter animal."
“When you first adopt an abused shelter animal, when you try to be kind to them, they recoil from that because they’re not used to that. They have to get used to you, to kindness, and people doing something for you where they don’t expect something back,” Oswalt continued. “That is so alien to Trump. Everything that’s ever been done to him, he had to pay for or give something back.”
Oswalt believes the cordial White House dinner, which turned sour only after Maher had left, is indicative of Trump’s mistrust of his peers.
“You could see in Trump’s head, like, ‘What is this? This guy’s gonna want something,’ and he got on the defensive and then started attacking him, which is all Trump knows,” he explained.
“And that’s something that I actually have some sympathy with him for,” Oswalt continued, before quickly correcting himself. “Or I would have sympathy for him if he were in his 20s. But by the time you reach the age that Trump is, work your stuff out, man. You gotta work your s--t out.
Oswalt, who attended Stephen Colbert’s The Late Show final episode after-party, said the affair was strangely uplifting.
“It wasn’t surreal. It was very, very real,” he said. “This thing had been coming.“
“What ended up happening was I ended up being kinda hopeful because who was there,” he said, listing off celebrities ranging from Lin-Manuel Miranda to Sacha Baron Cohen to journalist Terry Gross to Bette Midler.
“Stephen Colbert was dancing with his wife, and everyone’s around him, and someone said, ‘This is arguably the worst day of Stephen Colbert’s career—which is far from over—and he is happier than Trump will ever be on the best day of his life,“ he concluded. ”Trump will never know this happiness."
Tea & Scotch is currently available to watch on YouTube and GorillaComedy+.
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