Honestly, if you missed the window back in 2016 when Funny Or Die dropped a full-length feature film out of nowhere, you missed one of the strangest moments in internet history. It was Super Tuesday. The political world was melting down. Then, suddenly, a 50-minute parody titled Donald Trump's The Art of the Deal: The Movie appeared on the homepage of a comedy site, starring Johnny Depp. Yes, that Johnny Depp. Under layers of heavy prosthetics and a wig that looked like it was made of spun sugar and spite, Depp channeled the 1980s version of the future president.
It wasn't a biopic. Not really. It was presented as a "lost" TV movie from 1988 that Trump supposedly wrote, directed, and edited himself, only for it to be suppressed by a disgruntled TV executive because a football game ran long. It’s chaotic. It’s loud. It captures a specific era of New York greed that feels like it belongs in a museum, or maybe a fever dream.
The strange origin of the film nobody saw coming
The production was a massive secret. In an era where every casting choice leaks on Reddit three months before filming starts, the crew managed to keep Johnny Depp’s involvement totally under wraps. They filmed it in about four days. That’s insane for a feature-length project. Director Jeremy Konner, known for Drunk History, and writer Joe Randazzo, a former editor at The Onion, treated the source material—the actual 1987 memoir The Art of the Deal—as a holy text to be mocked.
The movie frames itself around a kid who wanders into Trump Tower. Trump (Depp) then decides to mentor this child by recounting the "chapters" of his life. It’s a framing device that allows the movie to jump through time, covering the acquisition of the Taj Mahal casino, his marriage to Ivana, and the construction of Trump Tower.
Why does this matter now? Because it’s a time capsule of how Hollywood viewed Trump just before the 2016 election shifted from a joke to a reality.
Johnny Depp and the art of the transformation
Depp’s performance is the only reason the movie works. He doesn't just do a "Saturday Night Live" impression. He goes darker. He captures the specific cadence of 80s Trump—the breathy pauses, the aggressive hand gestures, and that specific brand of over-the-top confidence. It’s unsettling.
✨ Don't miss: Cuba Gooding Jr OJ: Why the Performance Everyone Hated Was Actually Genius
The supporting cast is equally bizarre. You’ve got Patton Oswalt playing Jack Kanter, Alfred Molina as Jerry Schrager, and even Henry Winkler as Ed Koch. Michaela Watkins plays Ivana Trump with a sharp, satirical edge that cuts through the silliness. Even Christopher Lloyd pops up as Doc Brown in a weird Back to the Future crossover beat that makes zero sense but fits the "lost 80s tape" aesthetic perfectly.
The lighting is grainy. The music is pure synth-pop trash. It feels like something you’d find on a dusty VHS tape at a garage sale in Queens. That was the point. They wanted to recreate the ego-driven vanity projects that wealthy moguls actually produced during the Reagan era.
What most people get wrong about the satire
People think Donald Trump’s The Art of the Deal: The Movie is just a political hit piece. It’s actually more of a critique of 1980s materialism. It targets the aesthetic of success. The film leans heavily into the advice given in the real book—things like "Think Big" and "Maximize Your Options"—but shows them as tools for a man who is essentially a child in a suit.
One of the funniest, yet most telling, sequences involves the negotiation for the Taj Mahal. In the movie, Trump treats the acquisition like a high-stakes spy thriller, despite it being a mess of debt and bureaucratic hurdles. It mirrors the real-life criticism often leveled at the book's ghostwriter, Tony Schwartz. Schwartz has famously since distanced himself from the work, claiming he "put lipstick on a pig." The movie leans into this, suggesting the "art" of the deal is mostly just relentless self-promotion.
The film also tackles the "John Miller" and "John Barron" personas. For those who aren't deep into the lore, these were pseudonyms Trump reportedly used to call reporters and brag about himself in the third person. In the movie, Depp handles these moments with a wink to the camera that feels both hilarious and deeply cynical.
🔗 Read more: Greatest Rock and Roll Singers of All Time: Why the Legends Still Own the Mic
Does it still hold up as a movie?
If you're looking for a tight narrative, you’re going to be disappointed. It’s a sketch show disguised as a film. It drags in the middle. Some of the jokes are dated, relying on the shock value of seeing A-list actors in a low-budget web production. But as a piece of performance art? It's kind of brilliant.
The soundtrack is a standout. Kenny Loggins actually wrote and performed a theme song for it. Think about that. The man who gave us Footloose and Danger Zone sat down and wrote a power ballad about real estate development. It is peak 1988.
Why the "lost footage" gimmick worked
The 4:3 aspect ratio and the tracking errors on the screen make you feel like you're watching a broadcast from a dead civilization. It’s a clever way to mask a low budget, but it also serves the theme. Everything about the 80s Trump brand was about gold-plated surfaces. The movie strips that away by showing the "tape" as degraded and cheap.
The real legacy of the Funny Or Die experiment
At the time, this was one of the most ambitious things a digital comedy platform had ever tried. They weren't just making a five-minute clip; they were making a statement. They wanted to see if they could influence the news cycle by dropping a "bomb" of content.
- The Cast: Seeing Ron Howard introduce the film as if he found it in a yard sale added a layer of faux-prestige.
- The Timing: Releasing it during the primary season ensured maximum visibility.
- The Tone: It stayed weird. It didn't try to be a "preachy" political documentary. It stayed in the realm of the absurd.
The movie eventually made its way to streaming services like Netflix and is still floating around the internet. It serves as a reminder of a very specific moment in the American zeitgeist when the line between entertainment and politics completely dissolved.
💡 You might also like: Ted Nugent State of Shock: Why This 1979 Album Divides Fans Today
How to watch it and what to look for
If you decide to track down Donald Trump’s The Art of the Deal: The Movie, don't go in expecting a traditional comedy. Expect a satire of an ego. Look closely at the background details—the ridiculous gold statues, the specific brand of bottled water, the way the extras react to Trump's outbursts. It's a masterclass in set design as parody.
The film remains a polarizing piece of media. Some see it as a prophetic warning; others see it as a mean-spirited caricature. Regardless of where you land, it’s a fascinating look at how we process public figures through the lens of pop culture. It captures a version of the "American Dream" that is all about the sale, regardless of what's actually being sold.
Actionable insights for the curious viewer
To get the most out of this bizarre cinematic artifact, you have to understand the context of the era it mocks.
- Read the original book first: Or at least the SparkNotes. The movie makes specific references to the "eleven steps" outlined in the real Art of the Deal. Seeing how they twist those steps into comedy is the best part of the experience.
- Research the 1980s USFL lawsuit: The movie devotes a significant chunk of time to Trump’s involvement with the New Jersey Generals and his lawsuit against the NFL. It’s a real-life event that is even crazier than the movie depicts.
- Focus on the prosthetics: Johnny Depp spent hours in the chair for this. The makeup team actually won an Emmy for their work. Watching the subtle movements of the facial appliances shows the level of detail that went into a "throwaway" internet movie.
- Check the credits: There are cameos from people like Stephen Merchant, Andy Richter, and Will Arnett. It’s a "who’s who" of 2010s comedy buried under 1980s hair.
The film is a relic of a time when we thought satire could change the world. It didn't, but it sure made for a strange 50 minutes of television. Whether you find it hilarious or exhausting, it stands as a unique moment where the world of "A-list" Hollywood and "guerrilla" internet comedy collided to tackle the biggest personality in modern history.