Woody Allen, the legendary and often controversial filmmaker, has found himself back in the spotlight for a most unexpected reason: his outspoken admiration for the acting chops of none other than President Donald Trump. On September 1, 2025, Allen, now 89, appeared on Bill Maher’s podcast Club Random and delivered a string of surprising compliments about Trump’s performance in the 1998 film Celebrity, which Allen himself directed. The comments have since ignited a flurry of discussion across social media and traditional news outlets alike, with Trump himself enthusiastically amplifying the praise on his own platform, Truth Social.
“He was a pleasure to work with and a very good actor. He was very polite, hit his mark, and did everything correctly,” Allen recalled, his words echoing across outlets from Fox News to The New York Post. The director, who has helmed more than 50 films and won four Academy Awards, seemed genuinely impressed by Trump’s on-set demeanor and what he called a “real flair for show business.”
It’s not every day that a Hollywood legend heaps praise on a sitting president, especially one as polarizing as Trump. Allen, however, was quick to clarify that his admiration is strictly professional. “No, I’m not a Trumper. I’m one of the few people who can say he directed Trump,” Allen told Maher. He emphasized that he disagrees with Trump on “95% of the things, maybe 99%,” and, for good measure, added, “I’m a Democrat. I voted for Kamala Harris” in the 2024 presidential election.
Despite those political differences, Allen couldn’t help but marvel at Trump’s on-screen presence. “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,” the director mused. “Politics is nothing but headaches, and critical decisions, and agony. This was a guy I used to see at the Knicks games.”
The recollection of Trump’s cameo in Celebrity paints a vivid picture. In the film, Trump appears as himself, sharing the screen with actress Judy Davis. The scene is pure Trump: he jokes about buying St. Patrick’s Cathedral and replacing it with a “very, very tall and beautiful building.” According to The New York Post, the real estate mogul’s performance was delivered in a quintessentially understated tone, poking fun at his own reputation and penchant for grandiosity.
Trump’s brief but memorable appearance in Celebrity was just one of several cameos he made during his pre-presidential years. He also popped up in films such as Home Alone 2: Lost in New York (1992), The Little Rascals (1994), Eddie (1996), and Zoolander (2001). Yet, the cameo in Allen’s film stands out, perhaps because of the director’s unique perspective and willingness to publicly praise Trump’s abilities—despite their political gulf.
Allen’s remarks didn’t go unnoticed by Trump. On September 1, the president reposted an article about Allen’s comments on Truth Social, his preferred social network. The move was classic Trump: quick to seize on positive press, especially when it comes from a member of the Hollywood elite not typically counted among his supporters.
The exchange between Allen and Maher on the podcast was as entertaining as it was revealing. Maher, who has long been a sharp critic of Trump, reacted with mock outrage to Allen’s praise. “How dare you?” he joked, before adding with a dose of sarcasm, “Oh, if you think you were canceled before…”—a reference to the longstanding controversies surrounding Allen, including allegations of sexual abuse by his daughter Dylan Farrow and his marriage to his adopted stepdaughter Soon-Yi Previn. Allen has consistently denied the allegations.
Maher, for his part, agreed with Allen’s assessment that Trump is different in person than in his public persona. The comedian recounted his own experience meeting Trump at the White House earlier in 2025, noting, “Yeah, he’s different in person, and when you say that, people who are purely emotional get very upset, even though it’s just the truth. We’re just saying the truth.”
Allen, ever the director, even joked about wanting to work with Trump again. “I wish I could direct him now. If he would let me direct him now that he’s president, I think I could do wonders,” he quipped. “I would like to direct him as president and have him let me make the decisions, but that’s not gonna happen.” Maher played along, promising to “make a call.”
But not everyone shares Allen’s rosy view of Trump’s acting prowess. As Ara pointed out, critics were far less impressed by Trump’s earlier forays into cinema. His performance in the 1989 film Ghosts Can’t Do It earned him a Golden Raspberry Award (Razzie) for worst performance, a dubious honor that stands in stark contrast to Allen’s effusive praise.
Still, Allen’s comments highlight the sometimes-blurry line between celebrity and politics in America. Trump, who spent decades cultivating his image as a brash businessman and reality TV star, brought those same skills to the political arena—much to the consternation of his critics and the delight of his supporters. Allen’s remarks, then, offer a rare glimpse into the crossover appeal that helped propel Trump to the highest office in the land.
Allen also expressed genuine puzzlement at Trump’s decision to enter politics. “Why anyone would want to suddenly have to deal with the issues of politics is beyond me, but apparently he doesn’t mind,” Allen said. He recalled seeing Trump at Knicks games and judging beauty pageants, suggesting that the world of politics—with its constant scrutiny and endless headaches—seemed an odd fit for someone so at home in the world of entertainment.
While Allen’s praise may not sway the opinions of Trump’s staunchest critics or most fervent supporters, it serves as a reminder that even in an era of intense polarization, there’s room for unexpected admiration across the aisle—at least when it comes to the art of performance. As Allen put it, “He was very easy to work with.”
And so, in a week where Hollywood and Washington once again collided, it was the unlikely duo of Woody Allen and Donald Trump who stole the show, reminding everyone that, in America, the line between politics and entertainment is sometimes just a camera’s lens away.
