Donald Trump’s Bad Romance with Hollywood Began Before Parasite

It took nearly two weeks after the Academy Awards telecast before President Donald Trump weighed in with his less than urgent Oscar night analysis. Standing before a fawning crowd of “Keep America Great Hats” in Colorado on Thursday evening, Trump had a seemingly sudden impulse to share his sour grapes about Parasite winning Best Picture at the Oscars—a first for a foreign language film.

“How bad were the Academy Awards this year?” Trump rhetorically asked a crowd that quickly booed in agreement. “Did you see it? And the winner is… a movie from South Korea!? What the hell was that all about? We got enough problems with South Korea with trade. On top of it, they give him [Bong Joon-ho] best movie of the year? Was it good. I don’t know. Let’s get Gone with the Wind, can we get Gone with the Wind back, please? Sunset Boulevard. So many great movies. The winner is from South Korea… did this ever happen before?”

It doesn’t take a Harvard Law degree to pick up on the xenophobic dog whistle in this characteristically scatter-brained ramble. The President of the United States, while on the campaign trail for reelection, decides it’s in the prudent interest of American voters to whine that a film co-written and directed by an Asian man, and starring a South Korean cast, won Best Picture while evoking “the good ol’ days” by referencing movies from 1939 and 1950, respectively. One of those films, Gone with the Wind, even made a tacit defense of slavery and “its pretty world [where] Gallantry took its last bow. Here was the last ever to be seen of Knights and their Ladies Fair.”

So a president who campaigned in 2016 on building a wall now complaining about a non-English movie that didn’t star white people is hardly surprising. In fact, it’s depressingly predictable, like Trump seemingly admitting he doesn’t have the attention span to watch a movie with subtitles (though on a personal note, I’m surprised he enjoyed Sunset Boulevard and its hardboiled evisceration of vanity and delusion).

But it also speaks to a continued bad romance that has now mutated into a bitter estrangement between Trump and the Hollywood conclave he was once so desperate to be amongst. For long before he was a politician, he was a real estate mogul with dreams of celebrity. Hence his infamously telling Billy Bush, “When you’re a star they let you do it, they let you do anything”—and his working to become one culminating in the NBC reality TV series, The Apprentice.

But even before Trump settled for reality TV, we would do well to remember that Trump at one point dreamed about being in the movies. In fact, he’s been on the set of quite a few of them.

To this day, it’s strange to think that Home Alone 2: Lost in New York (1992) has become a historical document that must be preserved in the Smithsonian, but here we are in a world where it featured an appearance from a future POTUS. You know the scene: Kevin McCallister (Macaulay Culkin) wanders into the crystal splendor of the Plaza Hotel by Central Park and asks a businessman for directions to the lobby. Amused and made curious by this precocious youth—so probably acting—Donald Trump directs him around the corner.

It’s a strange cameo, but it’s even stranger for why it appears in the movie: Trump apparently insisted that if Home Alone 2 filmed in the Plaza, he would have a cameo in the film. This is, in fact, how many (though not all) of his 1990s and 2000s cameos occurred. It was ironically Matt Damon who revealed as much when he spoke with The Hollywood Reporter in 2017.

When asked if he’s ever met Trump, Damon said, “No. The deal was that if you wanted to shoot in one of his buildings, you had to write him in a part. [Director] Martin Brest had to write something in Scent of a Woman—and the whole crew was in on it. You have to waste an hour of your day with a bullshit shot: Donald Trump walks in and Al Pacino’s like, ‘Hello, Mr. Trump!’ – You had to call him by name –and then he exits. You waste a little time so that you can get the permit, and then you can cut the scene out. But I guess in Home Alone 2, they left it in.”

Indeed, Trump did own the Plaza in the early ‘90s, but what he also had was a desire to be the center of attention. At the time of many of these cameos, including other films such as Zoolander (2001) and stints on TV shows like Fresh Prince of Bel-Air, Spin City, and Sex in the City, these appeared to be good natured self-deprecating shrugs wherein he would appear as a larger-than-life personality if not outright buffoon.

But in retrospect, each of these cameos, including on sitcoms where he was eagerly invited, all helped cultivate a certain image of a billionaire that everyone in the room would instantly admire. They also retroactively reinforce a personality that needs to be constantly adored. For instance, Trump had an entire supporting role where he played himself (without being outright called Donald Trump) in Ghosts Can’t Do It (1989). And what was that actual expanded role of? A rich businessman who both intimidates 10 star Bo Derek, but also earns her interest: “You’re too pretty to be bad,” she coos. Trump then pouts his lips and smirks, “You noticed?”

Before finally finding a niche that allowed him to be a TV star with The Apprentice, Trump chased this kind of celebrity and fame in Hollywood circles, even as it never quite materialized.

“I met [Trump] once at a Fashion Week event in Milan,” Ben Affleck once recalled to the Guardian in 2017. “You knew you were at a cheesy party if Donald Trump was there. He would kind of trawl around them.”

Affleck’s fellow Batman actor Christian Bale has his own unique memories of Trump, including when he met him while filming The Dark Knight Rises (2012). By the time of that film, Trump had apparently given up demanding cameos when film productions shot on his property. However, he still expected fealty and face-time with the stars, as one celebrity to another.

“I met him one time,” Bale told Variety in 2018. “We were filming on Batman in Trump Tower and he said, ‘Come on up to the office.’ I think he thought I was Bruce Wayne, because I was dressed as Bruce Wayne. So he talked to me like I was Bruce Wayne and I just went along with it, really. It was quite entertaining.”

Admittedly, all of these anecdotal stories just paint the portrait of a man who liked being part of the entertainment industry when the opportunity arose. Yet he never got closer to being Batman than forcing a Batman actor to come to his office and shake his hand, and despite his limited attempts at acting, he ended up on reality TV instead of at the center of the industry’s self-love on Oscar night.

One can’t help but wonder when he complains about the Oscars awarding Parasite if he just wishes they could give the Oscar to him? It might explain why he kept a fake Oscar replica in his Trump Tower office all those years…

David Crow is the Film Section Editor at Den of Geek. He’s also a member of both the Critics Choice Association and the Online Film Critics Society. Read more of his work here. You can follow him on Twitter @DCrowsNest.