Woody Allen Says Donald Trump Was a 'Pleasure to Work With' on Film Set
On Bill Maher’s podcast, the filmmaker recalled directing Trump in the 1998 film Celebrity and praised his on-camera performance
Woody Allen said Monday that former president Donald Trump was a “pleasure to work with” and “a very good actor” when Allen directed him in a cameo for the 1998 film Celebrity.
Speaking on Bill Maher’s Club Random podcast, the 89-year-old filmmaker said he was not a supporter of Trump but recalled the experience of directing the businessman-turned-politician. “No, I’m not a Trumper. I’m one of the few people who can say he directed Trump. I directed Trump in a movie… in ‘Celebrity.’ And he was, you know, he was a pleasure to work with and a very good actor,” Allen said.

In Celebrity, directed by Allen and released in 1998, Trump appears as himself in a brief scene with actress Judy Davis. In the exchange, the characters discuss tearing down St. Patrick’s Cathedral in New York City to replace it with “a very, very tall and beautiful building,” a line Allen cited while describing the cameo. Allen told Maher that Trump was “very polite and hit his mark and did everything correctly and had a real flair for show business.”

Allen’s remarks were part of a wider conversation on the podcast, which has frequently featured candid recollections from entertainers about their careers and collaborations. The director’s comments underscore a moment when Trump, before his political career, participated in Hollywood projects that often showcased celebrity cameos.
Celebrity, a satire of the entertainment industry, drew attention at the time for its ensemble cast and its critique of fame. Trump’s short role is among several high-profile cameos in the film, which centers on a journalist navigating celebrity culture. Allen’s memory of the set emphasizes the practicalities of directing such appearances, noting professionalism and punctuality as factors that contributed to a smooth shoot.

Allen did not expand on any political views about Trump beyond stating he was not a supporter. The director has not been closely associated with contemporary political endorsements in recent years, and his anecdote focused specifically on Trump’s performance and conduct on a film set more than two decades ago.
The Club Random episode was posted Monday. Maher’s podcast has served as a platform for long-form interviews and reminiscences from figures across entertainment, where guests often discuss past projects and working relationships in detail.