Woody Allen heaps praise on Trump in new podcast with Bill Maher: ‘He was a pleasure to work with’
Filmmaker Woody Allen had some unexpectedly kind words for President Donald Trump, complimenting his acting ability and on-screen presence during a recent appearance on comedian Bill Maher’s podcast, Club Random.
Allen, 89, recalled directing Trump in a brief cameo in his 1998 film Celebrity and described the future president as “a pleasure to work with.”
“I’m one of the few people who can say he directed Trump,” Allen said during the episode, released Monday. “He was very polite, hit his marks, and did everything correctly. A very good actor, actually.”
Maher responded with mock outrage: “How dare you?” But Allen stood by his assessment, noting that Trump had a natural charisma on camera. “I’m surprised he went into politics,” Allen added. “Politics is nothing but headaches, critical decisions, and agony. This was a guy I used to see at Knicks games.”

Despite the compliments, Allen made it clear he’s not a Trump supporter. Both he and Maher emphasized they voted for Kamala Harris in the 2024 election.
Trump seemingly appreciated the praise, reposting an article highlighting Allen’s comments on his Truth Social account.
Maher also acknowledged Trump’s “performer” side, saying he has distinctly different public and private personas—something the comedian compared to acting. Allen didn’t see a problem with that. “They all have to put on a certain patina for the public,” he said, even joking, “I would like to direct him now that he’s president.”
Maher himself faced criticism earlier this year after dining with Trump at the White House and offering surprisingly positive reflections afterward. “He laughs,” Maher said in a segment on Real Time. “Including at himself—and it’s not fake.”

In Celebrity, Trump plays himself in a satirical cameo, dining at an upscale New York City restaurant and poking fun at his real estate persona: “I’m working on buying St. Patrick’s Cathedral—maybe doing a little rip down job and putting up a very, very tall and beautiful building,” he quips.
The appearance is one of several cameos Trump made during his real estate mogul days, including roles in Eddie (1996), The Little Rascals (1994), and his most iconic screen moment in Home Alone 2: Lost in New York (1992).