Woody Allen Recalls Directing Trump in 1998 Film: ‘He Was a Pleasure to Work With’

Filmmaker Woody Allen recently reflected on his past experience working with President Donald Trump, praising his professionalism and on-screen presence during a podcast interview with comedian Bill Maher.

Appearing on Maher’s “Club Random” podcast on Monday, Allen, 89, discussed Trump’s brief cameo in his 1998 film “Celebrity” and said he remains impressed by the performance.

“I’m one of the few people who can say he directed Trump,” Allen said. “I directed Trump in a movie. He was a pleasure to work with and a very good actor. He was very polite and hit his mark and did everything correctly and had a real flair for show business.”

The director emphasized that his compliments were limited to Trump’s work in front of the camera and not his political career.

“Well, you know, I’m a Democrat. I voted for Kamala Harris. And I take issue with him on 95 percent of the things. Maybe 99 percent,” Allen said. “But as an actor, he was very good. He was very convincing, and he has a charismatic quality as an actor.”

Allen also expressed surprise that Trump, whom he often saw at New York Knicks games and social events, chose to enter politics. “Politics is nothing but headaches and critical decisions and agony,” he said. “This was a guy … he liked to play golf and he liked to judge beauty contests.”

“Why anyone would want to suddenly have to deal with the issues of politics is beyond me,” Allen added.

Maher interjected that politics itself can be seen as “the ultimate acting job.” Allen responded that while he disagrees with Trump’s policies, he found him easy to direct and “very professional, very polite to everyone.”

Allen joked that he would even like to direct Trump again in his current role, remarking, “I would like to direct him now that he’s president and have him let me make the decisions. But that’s not gonna happen.”

Trump’s cameo in “Celebrity” lasted only a few seconds but became one of several appearances he made in Hollywood films throughout the 1990s. In the scene, Trump, playing himself, tells a television host that he is working on a plan to purchase St. Patrick’s Cathedral in Manhattan to replace it with “a very, very tall and beautiful building.”

He also appeared in other movies, including 1992’s “Home Alone 2: Lost in New York,” 1994’s “The Little Rascals,” and 2001’s “Zoolander,” often portraying himself in short cameos.

Allen, one of the most prolific filmmakers of the past half-century, has written and directed more than 50 films, including “Annie Hall,” “Manhattan,” and “Midnight in Paris.” His work has earned him four Academy Awards.