Legendary filmmaker Woody Allen surprised listeners on September 1, 2025, when he praised President Donald Trump’s acting abilities during an appearance on Bill Maher’s “Club Random” podcast, describing the commander in chief as a professional and charismatic performer based on their collaboration nearly three decades ago.
The 89-year-old director, who cast Trump in a brief cameo for his 1998 film “Celebrity,” told Maher that the then-real estate mogul demonstrated genuine talent during the filming process. Allen noted that Trump hit his mark, followed directions correctly, and displayed a natural flair for show business during his 11-second appearance in the movie.
In the film, Trump played himself in a scene where he discusses purchasing Manhattan’s St. Patrick’s Cathedral with plans to demolish it and replace it with a very tall and beautiful building. Allen emphasized that Trump was polite to everyone on set and approached the role with professionalism, describing him as convincing and possessing a charismatic quality as an actor.
Despite his positive assessment of Trump’s acting abilities, Allen clarified his political stance during the podcast. The director revealed he voted for Kamala Harris in the 2024 presidential election and disagrees with Trump on approximately 95 to 99 percent of political issues. Allen specified that he was not a “Trumper” and emphasized he was evaluating Trump solely based on their professional interaction during filming.
Allen expressed surprise at Trump’s decision to enter politics, suggesting that the former real estate developer previously enjoyed leisurely activities. The director recalled seeing Trump at New York Knicks games and noted his involvement in golf and beauty pageant judging, questioning why anyone would choose to deal with the headaches and critical decisions inherent in political life.
The conversation took a lighthearted turn when Allen jokingly suggested he would like to direct Trump again, now that he serves as president. Allen quipped: “If he would let me direct him now that he’s president, I think I could do wonders.”
Maher responded to Allen’s comments with mock outrage, joking about potential backlash the director might face for speaking positively about Trump. The comedian noted similarities between his own recent experiences, referencing criticism he received earlier this year after dining with Trump at the White House and subsequently describing the president in favorable terms.
The podcast host had previously caught attention for his own positive remarks about Trump following their private meeting. Maher described Trump as gracious and authentic during their encounter, leading to satirical responses from other entertainment figures, including Larry David, who wrote a viral essay in The New York Times comparing such praise to complimenting Adolf Hitler.
During the discussion, Allen and Maher explored the relationship between politics and performance, with Maher suggesting that serving as president represents the ultimate acting job. Allen acknowledged that all politicians must present a certain image to the public but maintained his assessment was based solely on Trump’s professional conduct during their film collaboration.
Trump apparently appreciated Allen’s comments, sharing an article about the director’s praise on his Truth Social platform. The president’s decision to amplify the positive remarks reflects his ongoing efforts to garner support from Hollywood figures, despite typically receiving criticism from the entertainment industry.
The podcast appearance also touched on Allen’s broader career challenges in recent years. The director has faced difficulties securing film projects and experienced boycotts from major stars due to longstanding personal controversies. Allen acknowledged these challenges but indicated his established career provided some protection against the impact of such scrutiny.
Allen’s praise for Trump’s acting abilities represents a rare instance of positive commentary about the president from a prominent Hollywood figure. The director’s careful distinction between personal politics and professional assessment highlights the complex dynamics surrounding public figures’ interactions across political divides in the entertainment industry.
