Tim Allen Says One Conversation Convinced Donald Trump to Walk Away From Hollywood Movie Investing

Actor and comedian Tim Allen says a single conversation about the financial realities of Hollywood filmmaking was enough to convince President Donald Trump that movie investing was not a business he wanted to enter, as reported by Fox News.

Allen, 72, shared the story during a recent appearance on Club Random with Bill Maher****, hosted by Bill Maher.

During the discussion, Allen recalled explaining to Trump how film budgets work and how losses are often unavoidable, even for major studios.

“He says, ‘If we got a studio together, let’s say the movie costs a million six or a million twenty.’

And then I said, ‘You’ve got to double that at least for the promotion. So you got 210 into a movie, two hundred million into a movie.’ He goes, ‘What if the ticket sales are low?’ ‘You lose.’

And he goes, ‘But you got to make up the loss somehow. How do you make up the loss?’

I said, ‘Well, there’ll be some tax benefit, but you lose the money. That’s how come the studios struggle looking for winners. You amortize your loss with losers over winners.’

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He goes, ‘Oh.’ Like, he completely decided at that moment, I’m not going to get in this business,” Allen said.

Allen contrasted film investing with Trump’s background in real estate, saying the lack of tangible assets in movies made the risk unappealing.

“He says, ‘If I buy a bad building and it won’t sell, I still have the f—ing building. If you have a sh—y movie…’ This is not an easy business,” Allen added.

The “Last Man Standing” star has spoken openly in the past about his conservative views, particularly on fiscal issues. In a 2021 appearance on WTF with Marc Maron, Allen was asked whether he considered himself an “old-school conservative.”

Allen said he has long viewed himself as fiscally conservative and expressed frustration with the tax system.

“Once I started making money, I had this silent partner that just took almost half of my money and never gave me anything for it and that was the taxes,” Allen said.

“I’ve never liked taxes… That’s it, I don’t like it. I work pretty hard for this stuff, and I accomplished a lot, and I was handicapped by my own errors. It’s all my fault, I get that. But I had this silent partner. I never liked taxes.”

Allen confirmed that the “silent partner” he was referring to was the government.

During that same discussion, Allen explained why he has generally avoided publicly endorsing political candidates or turning his comedy into political messaging.

“I literally don’t preach anything,” he said.

“I’m not telling anybody else how to live. Once I realized that the last president pissed people off, I kind of liked that. So it was fun to just not say anything, [I] didn’t join into the lynching crowd.”

Allen has also spoken publicly about meeting Trump years before his presidency and said his private impression differed from Trump’s public persona.

In a 2018 interview with Entertainment Weekly, Allen recalled an early encounter with Trump at a charity event and said the experience did not align with how Trump was portrayed publicly at the time.

“I’ve met [Trump] at [a] charity event years ago, and that certainly doesn’t fit with the man who tweets,” Allen said.

“I’ve met a lot of people in private whose public persona is a bit off. My perception is ‘let’s see what he gets done.’ Let’s stop banging on the pilot’s door and trying to pull the guy out of his seat while he’s still flying. You might not like how he’s flying the plane, but let’s let him land it.”

Allen’s comments about Hollywood finances offered a rare inside look at why major outside investors often hesitate to fund large studio projects.

He explained that, unlike real estate or other asset-backed ventures, films can lose hundreds of millions of dollars without leaving behind anything of tangible value.

Studios routinely offset losses by spreading financial risk across multiple projects, hoping that a small number of successful releases will cover the failures.

Allen said that model was a key factor in Trump’s immediate loss of interest in the industry.

According to Allen, Trump’s reaction came quickly once the full scope of potential losses became clear.

Allen described the moment as decisive, saying Trump appeared to conclude almost instantly that movie financing did not align with his business instincts.

Allen has remained largely outside Hollywood’s political activism despite holding views that often place him at odds with the entertainment industry’s dominant culture.

He has repeatedly said he prefers to keep politics out of his comedy and public persona, even as his remarks periodically attract attention.

His recent comments on “Club Random with Bill Maher” added to that history, offering a candid account of a conversation that, in Allen’s telling, permanently closed the door on Trump becoming a Hollywood movie investor.

The story also highlighted the sharp contrast between Hollywood’s risk-heavy business model and Trump’s real estate background, where even failed investments typically retain underlying assets.

Allen suggested that difference alone was enough to end any serious discussion about Trump entering the film industry.

While Allen did not specify when the conversation took place, he said it left a lasting impression on both men and illustrated why Hollywood financing remains a difficult and often misunderstood business—even for experienced investors.

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