There are fewer than 100 days to go until the United States elects a new president, and billionaire real estate mogul Donald Trump has a chance. While most prediction models still show Hillary Clinton as the likely winner, Trump is polling better than he once was and the world is watching as the U.S. flirts with the idea of putting a wealthy individual with no political experience in the White House.

Some don’t consider this to be a bad idea. In fact, even Mitt Romney, who ran for president in 2012 and had governing experience, opted to tout his business record more than his political background during his campaign. As is true with many in the UK as well, a lot of Americans like the idea of an “outsider” assuming office. When they see billionaires, they think about job creation, wealth, and success.

But what can we learn about a figure like Trump from film? At this stage, there really isn’t a film about this exact scenario. But it’s interesting to note that most films about wealth or extremely wealthy individuals tend to put forth a similar message: money is hollow, extreme wealth is rarely gained honourably, and going it alone, even with all the money in the world, makes for a poor existence.

Let’s look at a few films that have taught these messages.

Citizen Kane (1941)

Arguably the closest thing to a look at the Donald Trump saga in cinematic history, Citizen Kane concerns a private citizen who inherited a fortune and set out to build a media empire and influence public opinion regarding the Spanish-American War. There’s more to it than that, but Charles Foster Kane is essentially on a quest to obtain wealth and influence at the expense of all else (though we view this largely through flashbacks and interviews with his associates).

Online magazine Le Monde Diplomatique actually explored the idea of whether or not a figure like Citizen Kane could exist today, with writer Ignacio Ramonet concluding that by today’s standards, Kane would be a small fry. He’s correct in asserting that owning a few papers (as Kane did) would earn one very little real influence in the age of television media. What’s not accounted for is the idea that a political figure could manipulate television media without actually owning it. In large part, this is what Trump has done to rise in the political world. So now, we see a strikingly similar figure, a businessman who inherited a fortune, inflated it over the years, and started seeking influence. The way Citizen Kane tells the story, however, a figure like Trump is in it for himself and likely to feel empty inside.

The Great Gatsby (2013)

There are several films based on F. Scott Fitzgerald’s novel, but we’ll look at the most recent—and, I would argue against the grain, the best—for this discussion. In any Gatsby film, the character is remarkably vibrant and wealthy. And at Lottoland, an online platform for EuroMillions lottery players, a ranking of the richest fictional characters has Jay Gatsby on the list (with an estimated £6.8 million net worth, which frankly seems a bit low). It’s an article meant to feed the imaginations of lottery players, but seeing Gatsby next to all those characters (Kane, for his part, is fifth on the list) emphasises that he’s not just a hard-partying socialite; he’s as rich as they come.

But as Leonardo DiCaprio portrayed arguably even more effectively than Robert Redford before him, this sort of wealth is hard to come by honestly, and there’s a deep loneliness that comes with it. DiCaprio’s Gatsby is plagued by a need to prove himself (in his case, to a woman), and conned his way to the top of the heap to do so. The trouble is once he’s there, he can hardly stop himself. This, too, seems to be a commentary on Trump, or at least the way some see him. Many have called into question the legitimacy of some of his business dealings, and he seems to operate with an inexplicable chip on his shoulder that makes him something of a loner.

The Wolf Of Wall Street (2013)

Not to stick with DiCaprio, but some of Trump’s biggest critics might find more similarities in The Wolf Of Wall Street’s Jordan Belfort than in Gatsby or Kane. Belfort, as you know if you saw The Wolf Of Wall Street, built a massive investment empire on fraud and lived an out of control, lavish lifestyle along the way. There’s no accusation here that Trump has done anything of the sort, but as stated there are those who doubt the legitimacy of some of his business dealings—and there’s no questioning that he’s lived a lucrative lifestyle on top of his heaps of wealth.

But the lesson with Belfort that some would say may end up applying to Trump is actually what happened to him after the events of The Wolf Of Wall Street. According to Time Magazine, which did a write-up of the real life character following the release of the 2013 film, Belfort can still make $100 million in a given year through speaking fees. This is a man who committed enormous crimes and went to prison for a relatively brief time only to come out as a free man with all the tools to earn incredible amounts of money. There is a similarity there, given the speed with which Trump seems to move from one legal proceeding to the another without slipping up or losing his ability to generate income. The troubling lesson with this comparison is that while there’s a hollowness to wealth, the ability to earn millions might just become perpetual when a businessman reaches a certain point.

Again, there’s no one film that perfectly sums up the man the U.S. is flirting with for electing president. But by looking at characters in cinema, you can certainly make some (mostly troubling) connections. At least in cinema, men like this tend to be lonely and dangerously ambitious, and the sum of their parts is seldom worth the whole.

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