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Woody Allen praises Donald Trump's acting: 'Pleasure to work with'

'He did everything correctly and had a real flair for show business'

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Woody Allen might disagree with U.S. President Donald Trump “99%” of the time. But that doesn’t mean Trump isn’t a good actor.

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On the contrary, says Allen, who directed the commander-in-chief in his 1998 dramedyCelebrity.

“I’m one of the few people who can say he directed Trump. I directed Trump in Celebrity,” Allen recalled this week on Bill Maher’s Club Random podcast. “He was a pleasure to work with, and a very good actor, and very polite. He did everything correctly and had a real flair for show business. If he would let me direct him now that he’s president, I think I could do wonders.”

Maher told the 89-year-old filmmaker, who has faced allegations of abuse, that his comments were likely going to cause controversy. “If you think you were cancelled before …” he said laughingly.

But the four-time Oscar winner said that he was strictly praising Trump’s skills as an actor.

“I’m a Democrat. I voted for Kamala Harris. I take issue with (Trump) on 95% of the things, maybe 99%,” Allen said. “But as an actor, he was very good. He was convincing and had a charismatic quality … I’m not a Trumper … I’m one of the few people who can say he directed Trump.”

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But Allen admitted that he was shocked to see Trump’s political transformation.

“I’m surprised he wanted to go into politics,” he said. “Politics is nothing but headaches and critical decisions and agony. This was a guy I used to see at the Knick 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.”

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President Donald Trump holds the FIFA World Cup Winners Trophy during an announcement in the Oval Office of the White House, Friday, Aug. 22, 2025, in Washington. Photo by Jacquelyn Martin /AP

In Celebrity, Trump appeared as himself in a scene where he joked about buying New York City’s famous St. Patrick’s Cathedral and tearing it down.

“Maybe doing a little rip-down job and putting up a very beautiful building,” the then-real estate tycoon says in the movie.

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In addition to his part in Celebrity, Trump also appeared in 1994’s The Little Rascals, 2001’s Zoolander and 2002’s Two Weeks Notice, among other films.

His most notable role came during a scene in 1992’s Home Alone 2: Lost in New York in a scene in which Macaulay Culkin’s Kevin McAllister asks for directions to the lobby inside the Plaza Hotel (which Trump owned at the time).

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Macaulay Culkin and Donald Trump in a scene from Home Alone 2: Lost In New York. Photo by 20th Century Fox

In 2019, the CBC made headlines after it cut Trump’s cameo from its airing of the holiday favourite for “time’s sake.” The broadcaster said the U.S. leader had been edited out in 2014 before his political career.

“The scene with Donald Trump was one of several that were cut from the movie as none of them were integral to the plot,” Chuck Thompson, a spokesman for the broadcaster wrote on Twitter. But that didn’t stop Trump from angrily lashing out on social media.

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“I guess Justin T doesn’t much like my making him pay up on NATO or Trade!” Trump tweeted, targeting then-Prime Minister Justin Trudeau. His son, Don Jr., also blasted the omission, calling the edit, “absolutely pathetic.”

After the Capitol Hill riots in early 2021, Culkin endorsed dropping Trump’s scene from future broadcasts.

Meanwhile, in an interview with Insider in November 2020, Home Alone 2 director Chris Columbus claimed Trump bullied his way into the movie.

“He said, ‘The only way you can use the Plaza is if I’m in the movie,’” Columbus said. “So we agreed to put him in the movie, and when we screened it for the first time the oddest thing happened: People cheered when Trump showed up on screen.”

mdaniell@postmedia.com

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