Woody Allen Says Donald Trump Was ‘Polite’ and ‘a Pleasure to Work with’ When He Directed President in 1998

Woody Allen Recalls Working with Donald Trump on Set of ‘Celebrity’

Legendary filmmaker Woody Allen recently shared his experience of directing former President Donald Trump in his 1998 film ‘Celebrity,’ describing it as “a pleasure.” In a podcast appearance on Bill Maher’s Club Random, Allen remarked that despite disagreeing with most of Trump’s policies, he found the then-businessman to be professional and polite on set.

During the podcast, Allen praised Trump’s performance on camera, stating that he was “very polite and hit his mark and did everything correctly.” The filmmaker expressed his surprise at Trump’s transition from show business to politics, noting that he had always seen him enjoying leisurely activities like attending basketball games and playing golf.

Allen, known for his iconic works such as ‘Annie Hall’ and ‘Manhattan,’ reflected on his interaction with Trump during the filming of ‘Celebrity.’ The movie boasted a star-studded cast including Kenneth Branagh, Judy Davis, Winona Ryder, Leonardo DiCaprio, and Charlize Theron. Trump made a cameo appearance as himself in a scene where he discussed grandiose real estate plans for New York City.

Despite their collaboration on the film, Allen clarified that he did not share Trump’s political views. In fact, he revealed that he voted for former Vice President Kamala Harris in the 2024 U.S. presidential election and disagreed with Trump on a majority of his policies. However, Allen commended Trump’s acting skills and charisma, acknowledging his effectiveness as an actor.

Throughout his career, Trump made cameo appearances in several films and television shows, often playing himself. From ‘Home Alone 2: Lost in New York’ to ‘Zoolander,’ Trump’s forays into the entertainment industry prior to his political career were marked by guest roles that capitalized on his larger-than-life persona.

In light of his experience working with Trump, Allen entertained the idea of directing the former president again, expressing confidence in his ability to bring out Trump’s performance. Despite their differing ideologies, Allen’s remarks shed light on a lesser-known facet of Trump’s past and the interactions he had within the entertainment world.

As Allen’s comments sparked a discussion about Trump’s multifaceted background, it highlighted the nuances of individuals’ experiences and interactions, irrespective of their contrasting political beliefs. The filmmaker’s anecdote serves as a reminder of the complexities within personal relationships and collaborations, transcending the boundaries of ideology.

With Allen’s recollection adding a new dimension to Trump’s public image, it underscores the diversity of perspectives that shape our understanding of public figures. As the conversation surrounding Trump’s cameo in ‘Celebrity’ resurfaces, it prompts reflection on the intersection of entertainment, politics, and individual experiences in the realm of celebrity culture.