In what might be the most unexpected plot twist of 2025’s already bizarre entertainment landscape, Woody Allen — yes, that Woody Allen — has emerged as Donald Trump’s latest cheerleader. Well, sort of.
The praise isn’t political (thank goodness, because who needs more of that?). Instead, Allen’s surprising endorsement focuses squarely on Trump’s forgotten stint as an actor in Allen’s 1998 film “Celebrity.” During a recent appearance on Bill Maher’s “Club Random” podcast, the four-time Oscar winner couldn’t help but gush about Trump’s on-screen presence.
“He was a pleasure to work with and a very good actor,” Allen declared, momentarily setting aside his Democratic leanings. The scene in question? A mere 11-second cameo where Trump essentially played himself — though looking back now, it feels more like an eerie prophecy. Trump’s character mused about demolishing St. Patrick’s Cathedral to build “a very, very tall and beautiful building.” Some things never change, right?
Here’s where it gets interesting. Allen — who’s quick to point out he disagrees with “99 percent” of Trump’s politics and voted for Kamala Harris — painted a picture of Trump as something of a natural performer. The former president apparently “hit his mark, did everything correctly and had a real flair for show business.” Who’d have thought?
The timing of these comments couldn’t be more peculiar. With the 2024 election aftermath still sending shockwaves through the country and Trump’s legal battles dominating headlines, Allen’s casual praise of Trump’s acting chops feels almost refreshingly… normal?
Bill Maher, ever ready with a zinger, couldn’t resist pointing out the potential fallout. “If you think you were canceled before…” he quipped to Allen, whose own controversial history has made him something of an expert in public opinion roller coasters.
Perhaps the most fascinating part of Allen’s reflection wasn’t about Trump’s acting at all. The director seemed genuinely perplexed by Trump’s career pivot. “This was a guy I used to see at the Knick games,” Allen mused, “and he liked to play golf, and he liked to judge beauty contests.” The unspoken question hung in the air: How did we get from there to here?
In a moment of what could only be described as peak 2025 surrealism, Allen even suggested he’d like to direct Trump again — this time as president. “Let me make the decisions,” he added with a hint of that classic Allen humor, acknowledging the sheer impossibility of such a scenario.
Maher, never one to miss an opportunity for commentary, wrapped it all up with a neat bow: “Politics is the ultimate acting job.” In an era where reality TV stars become presidents and social media influencers shape policy debates, truer words have rarely been spoken.
The whole exchange serves as a peculiar reminder of how entertainment and politics continue to blend in ways that would’ve seemed absurd even a decade ago. It’s also a testament to how even the most polarizing figures can occasionally be viewed through a different lens — even if it’s just for their ability to nail an 11-second cameo in a ’90s film.
Strange times indeed. But then again, what else would you expect from 2025?
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