Hollywood director Woody Allen stunned many by offering high praise for President Donald Trump’s professionalism when asked by comedian Bill Maher about working with him on a film set.
Allen, who cast Trump in his 1998 movie “Celebrity,” admitted that while he disagrees with the president politically, his experience with Trump in a professional setting was nothing short of positive.
Speaking with Maher during a recent appearance on the “Club Random” podcast, Allen noted that Trump had impressed him during their collaboration.
“He was a pleasure to work with and a very good actor. He was very polite and hit his mark and did everything correctly and had a real flair for show business,” Allen said, leaving Maher stunned.
🚨NEW: Dem Filmmaker Woody Allen — who once directed Trump — *HEAPS PRAISE* on president's acting🚨
"He was a pleasure to work with and a very good actor. He was very polite and hit his mark and did everything correctly and had a real flair for show business."@DailyCaller pic.twitter.com/tNJMzcjq46
— Jason Cohen 🇺🇸 (@JasonJournoDC) September 1, 2025
Maher immediately joked that Allen’s comments could put him in even hotter water with critics: “If you think you were canceled before …”
The joke was a jab not only at Allen’s own controversies but also at the cultural backlash that often follows anyone willing to compliment Trump in Hollywood circles.
Maher himself knows that firsthand, having drawn the left’s criticism for not only dining with the president but also for speaking positively about their interaction afterward.
🚨NEW: Bill Maher SCOLDS Sean Penn for saying he *wouldn't* have dinner with TRUMP🚨
MAHER: "You'll meet with f*cking Castro and Hugo Chavez — but not the President of the United States?"
PENN: "Yeah … if I were, let's say, representing a cause célèbre … I would not fool… pic.twitter.com/QNP9gcLwbZ
— Jason Cohen 🇺🇸 (@JasonJournoDC) June 15, 2025
In an April segment on “Real Time,” Maher told his audience that meeting Trump in person had surprised him.
“Just for starters, he laughs,” Maher said, explaining that he had never seen Trump laugh in public.
“But he does — including at himself — and it’s not fake. Believe me, as a comedian of forty years, I know a fake laugh when I hear it.”
That view carried into his conversation with Allen. “He’s different in person. And when you say that, people who are just purely emotional get very upset, even though it’s just the truth,” Maher remarked. “We’re just saying the truth.”
Allen went on to say that if he had the chance now, he would like to direct Trump again.
Bill Maher says he doesn't think Woody Allen committed any crimes against children, calls actors who regret working with Allen "a bunch of pussies", and that he thinks the documentary was biased.
He adds, "I definitely don't know". pic.twitter.com/wNO4cVwqHa
— Post-Left Watch (postleftwatch.bsky.social) (@PostLeftWatch) April 15, 2024
“I only wish I could direct him now,” Allen commented. “If he would let me direct him now that he’s president, I think I could do wonders. But he was very easy to work with.”
Despite acknowledging their political differences, Allen offered glowing praise for Trump’s charisma and talent.
“I am a Democrat. I voted for Kamala Harris. And I take issue with him on 95% of the things, maybe 99%,” Allen said.
“But as an actor, he was very good. He was very convincing and he had a charismatic quality as an actor.”
WOODY ALLEN: “I am a Democrat. I voted for Kamala Harris. And I take issue with [Trump] on 95% of the things. Maybe 99%. But as an actor, he was very good … But I would like to direct him now that he's president, and have him let me make the decisions.” pic.twitter.com/Okii0kcmfu
— Chief Nerd (@TheChiefNerd) September 1, 2025
Allen admitted he was shocked that Trump chose to enter the political arena at all.
“And I’m surprised he wanted to go into politics. Politics is nothing but headaches and critical decisions and agony,” Allen said.
He described Trump as a man he once saw at Knicks games and golf outings, someone who enjoyed beauty contests and leisure activities.
“And why anyone would want to suddenly have to deal with the issues of politics is beyond me,” he added. “But apparently he doesn’t mind.”
Maher, on his own podcast in July, shared that the outrage over his dinner with Trump highlighted a troubling tendency on the left.
“The stupidest thing the left does — and this dinner is a perfect example of it — is having this attitude toward the right that: ‘We won’t even break bread with you. We are so far above you that we won’t even sit down at the same table with you!’ That is their attitude — and that makes me sick too!” Maher said.
While Hollywood debates whether even mild praise for Trump is allowed, the president has been the subject of renewed speculation about his health.
False stories circulated last week suggesting Trump had been absent from the public eye for several days and could be unwell.
The rumors spread quickly before being undercut by sightings of the president leaving the White House to play golf at his Virginia club on Sunday and Monday.
The radical left is so sick and twisted… https://t.co/UNowbVSf5O
— Eric Trump (@EricTrump) August 31, 2025
Eric Trump blasted the narrative online, writing, “The radical left is so sick and twisted…” in response to a claim that his father had died.
President Trump himself dismissed the talk while golfing, telling those around him that he had “never felt better.”
The speculation emerged just days after the president held a more than three-hour press conference during a cabinet meeting at the White House.
Donald Trump speaks on his health:
“NEVER FELT BETTER IN MY LIFE.” pic.twitter.com/L2V6LU1F3L
— Pop Base (@PopBase) August 31, 2025
Over the weekend, Trump shared a photo on Truth Social showing him playing golf with former NFL coach Jon Gruden, though online critics questioned the timing of the image.
Trump played golf with former NFL Super Bowl champion head coach Jon Gruden — seen wearing a Trump hat — at his D.C. golf course. 👀 pic.twitter.com/L6OJQye3Jr
— johnny maga (@_johnnymaga) August 31, 2025
Gruden’s Instagram account showed him in the same attire on August 23, prompting debate over when the picture was taken.
Questions about the president’s health have circulated for months, particularly after cameras captured bruising on his hand during Oval Office press gaggles.
In addition, swelling in Trump’s ankles has been noticeable in some public appearances.
Trump is alive and well at his Virginia club.
Cry more, libs 🤣 pic.twitter.com/biawPNXrTc
— Sara Rose 🇺🇸🌹 (@saras76) September 1, 2025
In July, the White House disclosed that the president had been diagnosed with chronic venous insufficiency, a common vein condition that causes swelling in the lower legs.
White House physician Dr. Sean Barbabella described it as “benign and common” and attributed bruising on Trump’s hand to “minor soft tissue irritation from frequent handshaking” compounded by the president’s use of aspirin.
White House Press Secretary Karoline Leavitt reiterated that point after Trump’s meeting with French President Emmanuel Macron on August 24.
“President Trump has bruises on his hand because he’s constantly working and shaking hands all day every day,” Leavitt said.