As if we needed another reason to question Woody Allen’s judgment, the 89-year-old director praised President Trump as “polite” and “a pleasure to work with” on Bill Maher’s podcast, “Club Random.”
Allen, who cast Trump in a cameo appearance for his 1998 film “Celebrity,” said on Monday’s podcast that the then-real estate mogul “hit his mark, did everything correctly and had a real flair for show business.”
“As an actor, he was very good,” Allen said. “He was very convincing, and he has a charismatic quality as an actor. And I’m surprised he wanted to go into politics. Politics is nothing but headaches and critical decisions and agony.”
Trump’s latest critical decision as commander in chief? Sharing the filmmaker’s positive comments on his Truth Social account. Heavy hangs the crown …
But why would Trump even want Allen on his side?
Allen’s legacy as a groundbreaking filmmaker was tarnished by revelations about his personal life that emerged in the 1990s. It was revealed that he had a romantic relationship with his then-girlfriend Mia Farrow’s adopted daughter, Soon-Yi Previn. He was 56. She was 21. Allen’s own daughter with Farrow, Dylan, would later accuse Allen of sexually molesting her, claims that he denies. Even if fans want to separate the artist from news stories about the man, it’s difficult given that Allen’s films often reflect an obsession with youthful — and occasionally underage — women.
The president has been doing everything possible to bury his past associations with older men who allegedly prey on younger women. There’s this guy named Jeffrey Epstein …
There’s obviously no comparing Allen to the late convicted child sex trafficker, but why even open the door to such scrutiny? It’s because a compliment is a compliment, and there are so few of them coming from Hollywood that Trump could not help but copy, paste and post.
More troubling is that Allen now joins Maher in normalizing America’s first president who operates like a dictator, describing Trump as “pleasant,” “gracious,” even “measured.” Meanwhile, the White House is siccing militarized forces on American cities, trying to deport planeloads of children and attempting to rig the 2026 midterms.
Maher responded to Allen’s flattering words about Trump with mock outrage: “How dare you?!”
Allen may have surprised listeners who know the director as a master satirist of the flawed personality, but Maher was right on brand. The 69-year-old has forged a career playing to all sides of contentious issues while sincerely committing to none.
Earlier this year, the host of HBO’s “Real Time With Bill Maher,” who describes himself as a “vocal critic” of Trump, caught flak for dining with the president at Mar-a-Lago, then later describing Trump as “gracious,” “not fake” and that “everything I’ve ever not liked about him was absent.” He praised Trump for being “measured” and not like the “person who plays a crazy person on TV.”
Larry David, the creator of “Seinfeld” and star of “Curb Your Enthusiasm,” responded to Maher’s laudatory dinner recollection with a satirical essay in the New York Times titled “My Dinner With Adolf.” David wrote from the perspective of a “vocal critic” of the Nazi dictator who, over dinner, finds Hitler to be surprisingly “disarming” and “authentic.” The essay went viral.
During Monday’s podcast, Allen counterbalanced his kind words about Trump with the revelation that he voted for former Vice President Kamala Harris in the 2024 presidential election. He also said that he disagrees with Trump on “99%” of issues.
After wondering aloud why Trump went into politics, Allen said, “This was a guy I used to see at the Knicks 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.”
Perhaps it’s about seizing total power? Exacting revenge on enemies such as his former national security advisor John Bolton? Scrubbing the Epstein files? Profiting off his office?
But let’s get back to Allen.
The director reiterated that he disagreed “with many, almost all, not all, but almost all of his politics, of his policies. I can only judge what I know from directing him in film. And he was pleasant to work [with], and very professional, very polite to everyone…
“If he would let me direct him now that he’s president, I think I could do wonders.”
He kids. But it was only just a few days ago that Allen came under fire for virtually attending the Moscow Film Festival as a guest of honor. He praised Russian cinema and hinted at wanting to shoot a film in the country. After some “measured” thought, perhaps Putin will get a cameo.