The 10 Best Movies That Show The Dark Side of Hollywood

5. Swimming With Sharks (1994)

swimming with sharks

Seeing Frank Whaley and Kevin Spacey in a movie together is enough. Seeing Frank Whaley’s lowly assistant go Tarantino on Spacey’s abusive movie mogul/executive’s ass is almost heavenly. Cynical and brutally honest to the point of being nihilistic, Swimming With Sharks is both a forgotten gem of the nineties, and one of the most bitter Hollywood satires ever made.

Whaley relates everything in his life to the movies. Every major event in his life, he relates to the time period one of his favorite films came out. This is something every movie geek can relate to, but it can also help to explain why his character puts up with what he does and why he goes to the lengths he eventually goes to in order to succeed.

Swimming With Sharks is ultimately about the self-sacrifice one chooses to make in order to succeed in an absurdly competitive industry like Hollywood. Spacey teaches Whaley that those who want success badly enough in Hollywood are usually the ones who get it. What Whaley loses to obtain it, however, makes the reward seem trivial at best.

As Spacey tells Whaley near the climax of the film, “You have to earn it. You have to take it. You have to make it yours… Out here, it’s kill your friends, fuck your parents, and have a nice day!… You have to kick and fight and scratch your way there… Life is not a movie. Good guys lose. And love… Does not conquer all.” Swimming With Sharks shows us all this and more many times over, and will stay with you for a long time after it’s done.


4. Barton Fink (1991)

barton fink

Set in 1950’s Hollywood, Barton Fink is the Coen Brother’s Kakaesque/Lynchian nightmare vision of what it’s like to be a screenwriter for hire in the studio system.

John Turturro plays the title character, a New York playwright who has been brought to Hollywood by a very exuberant studio head (played with absurd grace by Michael Lerner) to work on a wrestling picture. The studio head, not knowing a word of what he’s saying, wants “that Barton Fink” feeling for the project and sends him off to write. Barton takes up in a moldy, near empty hotel and starts to work.

The only problem is, Barton doesn’t have much experience with wrestling or, as we come to learn, much experience with life outside of his own mind. He is writing for the “common man” that Hollywood panders to, but has no idea what that entails. Barton is the ultimate outsider in Hollywood: he is unique, he is an intellectual, and he is completely and utterly confused as to what he is doing there in the first place.

His alienation and lack of knowledge of the “common man” comes to a head when he begins conversing with an odd neighbor in his hotel, a traveling salesman played by John Goodman (in his truly ultimate Coen Brothers performance). “The life of the mind” that Barton is hoarding inside himself soon explodes in a psychotic climax that would require an entire article in and of itself to describe.

Barton Fink is ultimately, and simply put, the story of an artist who simply can’t relate to the outside world or to what mainstream Hollywood audiences and filmmakers want. More abstractly, it’s a flipping weird expressionistic head trip about writer’s block and a cautionary tale on not getting too close to anyone in a Hollywood hotel. Either way, it’s a view of Hollywood we haven’t quite seen before or since.


3. The Player (1992)

The Player (1992)

Robert Altman’s The Player is a thriller first: Tim Robbins plays a studio executive who is receiving threatening postcards from an anonymous screenwriter. Robbins rejects dreams for a living, and it could literally be one of hundreds of disgruntled writers he’s blown off in the past.

He eventually tracks down who he believes to be the culprit, kills him in a heated brawl, then continues receiving the threatening postcards, leading him to believe he’s killed the wrong man. Sounds like a standard, Hitchcockian thriller, right? Part of what makes The Player such a brilliant film in general is its layers.

Yes, it’s a standard thriller, but it goes so much deeper than that because of its awareness that it’s telling its story with the same artifice as the town the movie is set in. And that is exactly what makes The Player one of the best Hollywood satires of all time. It’s a movie about movies that knows it’s a movie. The movie is full of star cameos (Bruce Willis, Julia Roberts, John Cusack, Cher, Nick Nolte, etc.) that pop up throughout the film to remind you of the world you’re in.

The thriller aspects continue, a romance blossoms, tensions build, detectives searching for the truth just won’t let up on Robbins… It just becomes more and more of a movie. Robbins’ character, however, manages to survive and thrive through all of it. Throughout the film, Robbins often speaks of happy endings. All movies need to succeed, more than anything, are happy endings, and that is what is lacking in most the screenwriting pitches he hears.

At the end of The Player, of course he gets his happy ending. Not because he deserves it, not because it makes sense, but because that’s what the movies are supposed to give us. Altman gives us, Hollywood, and all his years of bitterness in the industry the biggest middle finger of them all with The Player’s “happy” ending… And being flipped off has never felt so good.


2. Sunset Boulevard (1950)


Sunset Boulevard shows the emptiness, loneliness, and rejection that awaits everyone at some point in Hollywood… Whether they’ve been struggling for success their whole lives or they whether they were once the brightest star in town, there are no Hollywood happy endings for anyone in Billy Wilder’s masterpiece.

Narrated by William Holden’s corpse floating in a pool (no, really, the movie’s narrated by a dead guy floating in a pool), Sunset Boulevard tells the story of a washed up screenwriter who gets involved with a former silent screen starlet played by Gloria Swanson.

Swanson is aging, unwanted, and completely alone in her Hollywood mansion. Her life is so empty that she holds a lavish funeral for her former pet monkey to find fulfillment. Her only living friend is her loyal butler (with a secret…), who also happens to be the sole author of all her adoring fan letters which keep her under the delusion she’s still a superstar. She pours her heart out into a script she just knows Cecille B. Demille will want to direct her in. “I am big, it’s the pictures that got small”, she tells Holden.

Holden’s character stays in her employ for a while, rewriting her “masterpiece” until it becomes quite clear that he is simply there for her amusement and to further her delusion. Swanson’s character, once young and beautiful, has been forgotten. And she is unable to face the reality, so much to the point that she murders Holden when he tries to tell her the truth.

When the news cameramen show up to the scene of her crime, it turns out to be the most fulfilling moment she’s had in years. “I’m ready for my close up, Mr. Demille…” Sunset Boulevard is the boldest cinematic proof there is that it’s most certainly not better to be a has been than it is to be a never was…


1. Mulholland Drive (2001)


The complete and utterly empty and lonely mindfuck that it is to be a struggling wannabe anything in Hollywood is perfectly and brilliantly represented in David Lynch’s accidental masterpiece, Mulholland Drive. Naomi Watts’ lead character is a woman so delusional and in love with the fantasy of a Hollywood life that we see her create one. We see her arrive in Hollywood, nothing but stars in her eyes.

Everyone is friendly, telling her they “can’t wait to see her on the big screen.” She gives dazzling auditions with no previous experience other than winning a jitterbug contest in the Midwest. The only reason she’s not an immediate star is because of strange forces conspiring against her and the brilliant director who sees how fantastic she is…

Mulholland Drive is the perfect expressionistic point of view of every single person who has ever had high hopes and low failures in Hollywood. Watts’ ego can’t stand being another unknown in a town overcrowded with dreams, so she creates her own reality to excuse her failures, shortcomings, and, ultimately, her crimes.

While abstract and “Lynchian” on the surface, Mulholland Drive is arguably one of Lynch’s most straightforward films. It’s a nightmarish Wizard of Oz that takes you all the way down the yellow brick Hollywood boulevard of broken dreams… And it’s a place where no one gets out alive, especially in the mind of David Lynch.

Author Bio: Matt Hendricks is an independent filmmaker with several projects currently in development.