Woody Allen Says Directing Donald Trump in ‘Celebrity’ Was ‘a Pleasure’

Woody Allen is weighing in on his experience directing president Donald Trump in his 1998 movie Celebrity.

Allen, 89, discussed his time working with Trump, 79, during his appearance on the Monday, Sept. 1 episode of Bill Maher‘s Club Random podcast, which marked a rare recent interview for the four-time Academy Award-winning filmmaker as he promotes his new novel What’s with Baum?

At the end of Allen’s podcast appearance, the writer-director noted that while he is “not a Trumper,” he identified himself as “one of the few people who can say he directed Trump.” Celebrity, a comedy-drama, starred Kenneth Branagh and Judy Davis as a divorcing couple.

“I directed Trump in a movie, in Celebrity, and he was a pleasure to work with and a very good actor,” Allen said. “He was very polite and hit his mark and did everything correctly and had a real flair for show business. I only wish I could direct him now — if he would let me direct him now that he’s president I think I could do wonders. But he was very easy to work with.”

Trump made a cameo in Celebrity as himself in a scene that features Davis’ character Robin Simon as she hosts an interview show at a New York City restaurant. In the movie, Robin asks Trump what he’s “working on,” to which the then-real estate mogul suggests he wants to purchase St. Patrick’s Cathedral in Manhattan and replace it with “a very tall and beautiful building.”

Allen was quick to remind Maher and his podcast audience that while he recalls having a positive experience with Trump on the set of Celebrity, he voted for former vice president Kamala Harris in the 2024 U.S. presidential election and “[takes] issue with him on 95% of things, maybe 99%.”

“But as an actor, he was very good. He was very convincing and he has a charismatic quality as an actor and I’m surprised he wanted to go into politics,” Allen said of Trump. “Politics is nothing but headaches and critical decisions and agony. This was a guy I used to see at the Knicks games, and he liked to play golf, and he liked to judge beauty contests, and he liked to do things that were enjoyable and relaxing. Why anyone would want to suddenly have to deal with the issues of politics is beyond me, but apparently he doesn’t mind.”

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In the decades before Trump began pursuing the presidency, the businessman turned television host made cameos and guest appearances in a number of movies and television series, generally as himself. Most famously, Trump portrayed himself in 1992’s Home Alone 2: Lost in New York, but he also played roles in 1994’s The Little Rascals, 1996 movies like Eddie and The Associate, 2001’s Zoolander and 2004’s Marmalade, among other films. 

“I disagree with almost all, not all, but almost all of his policies, but I can only judge what I know from directing him in the film and he was pleasant to work with, very professional, very polite to everyone,” Allen recalled on Maher’s podcast. “As I say, 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.”