Woody Allen just stirred the Hollywood pot with some eyebrow-raising comments about Donald Trump—but not in the way you might expect.
During an appearance on Bill Maher’s “Club Random” podcast, the 88-year-old filmmaker opened up about working with Trump on his 1998 film Celebrity. While he made it clear he doesn’t align with Trump politically, Allen surprisingly praised the former president’s professionalism and acting chops.
“He was pleasant to work with, very professional, very polite to everyone,” Allen recalled, calling Trump a “great professional actor.”
Trump’s Cameo in Celebrity
For those who forgot (or weren’t old enough to catch it back then), Trump made a brief cameo in Allen’s 1998 movie Celebrity.
In the scene, Trump appears as himself, boasting about plans to buy St. Patrick’s Cathedral, tear it down, and replace it with a “very tall and beautiful building.”
It was a tongue-in-cheek cameo that now feels almost prophetic, considering Trump’s larger-than-life real estate persona and eventual pivot into politics.
Allen Clarifies His Politics
When Maher pointed out that Allen’s praise might rub people the wrong way, Allen quickly clarified his stance:
- He does not support Trump politically.
- He revealed that he actually voted for Kamala Harris.
- His comments were strictly about Trump as an actor on set, not as a political figure.
Woody even joked that his dream would be to direct Trump again—this time in the Oval Office—but with “a few more liberal policies.”
Politics as Acting?
Maher steered the conversation toward politics as performance art, suggesting that the presidency is “the ultimate acting gig.”
Allen agreed, saying he doesn’t get hung up on Trump’s persona so much as his policies. For Allen, the distinction between performance and politics is crucial—though fans online are already debating whether the two can really be separated.
Two Hollywood Outsiders
In an ironic twist, both Allen and Trump now find themselves as outsiders in the entertainment world.
- Allen, once considered one of Hollywood’s most prolific filmmakers, has faced years of controversy and limited distribution in the U.S.
- Trump, meanwhile, has remained a polarizing figure—shunned by much of Hollywood even as he remains a cultural force.
Still, Allen’s comments suggest that, at least in his eyes, there’s room for a surprising reunion down the road.
What’s Next?
Whether or not a Woody Allen–Donald Trump collaboration ever happens, the podcast clip is already sparking heated conversations online. Some see it as harmless nostalgia, while others view it as another example of how Hollywood and politics continue to blur.
For now, one thing is certain: Allen’s unexpected praise has reignited curiosity around Celebrity, a film that—like its infamous cameo—might just feel more relevant today than when it premiered 25 years ago.
Do you think Woody Allen’s praise was harmless, or is it a bad look to compliment Trump at all in 2025? Drop your thoughts below.
