The 10 Best Movies That Show The Dark Side of Hollywood

movies about hollywood

Hollywood is a glamour machine that spews out our greatest hopes, our highest ambitions, and our most personal dreams. More often than not, Hollywood films show us the world as we want it to be, ignoring the harsh realities that might leave us depressed or, even worse, leave producers with poor ticket sales to their latest release.

It’s a place and a business where anyone can make something of themselves, and part of its ongoing success lies in making us all believe that stardom and fortune could happen to all of us, too…

The following films shed light on that fabrication, showing Hollywood for the brutal factory of crushed dreams it actually is. Whether they depict people struggling to make it in the industry, the sociopaths who actually run it, or everyone else who just exists in the background, the following films focus less on the celebration of Hollywood’s artifice and more so on its deconstruction.


10. Grand Canyon (1991)

Grand Canyon

Lawrence’s Kasdan’s overlooked 1991 ensemble character piece covers a wide range of topics against its Los Angeles backdrop: racism, adultery, child abandonment, aging, and, of course, the movies.

Steve Martin’s supporting turn as a Joel Silver-type producer of violent action movies steals the show. In his introductory scene, we see him lambast his editing team for removing a shot of a bus driver’s brains splattered over a rearview mirror. He soon has a change of heart, however, when he becomes a victim of a violent mugging that leaves him shot in the leg and partially crippled for life.

Martin’s journey isn’t the focal point of Grand Canyon, but it certainly provides a bleak look into the heart of the movie industry. For a moment, Martin vows to never make a violent film again, to only make films for the good of humanity from that point on.

He has “seen the light”… And that “light” lasts about a minute or two before, in his next scene, he’s shrugging off his ideals with a “fuck that” and a monologue excusing his pursuit of violent action movies: The world is a violent place, the movies just reflect that, and it’s what people what to see. “All of life’s riddles are answered in the movies”, Martin tells his friend. And with the movies Martin’s character creates, it’s a cynical life, indeed.


9. The Big Picture (1989)


Kevin Bacon stars as an idealistic young filmmaker who has just graduated from film school. He’s the flavor of the moment, studios and agents are taking meetings with him, and he repeatedly pitches his black and white dream project that is a love triangle between three middle-aged adults.

Bacon’s character quickly experiences the “I love it! Let’s change everything about it!” mentality with which studio films are made. He immediately loses his ideals, changes the project into a film he can’t even recognize about twenty-somethings on the beach, and leaves his longtime love for Teri Hatcher’s wannabe starlet who’s not at all shy about overtly using anyone she can to get ahead in that town.

Director Christopher Guest makes a very accessible, silly, and, in the end, quite optimistic fable about trying to make it in Hollywood. It’s a very endearing, very quirky, and very sweet cautionary tale about the dark side that goes on behind the scenes of all our favorite Hollywood movies.


8. Mistress (1992)


The Big Picture’s darker, more cynical younger brother, yet equally (but more painfully) hilarious. Anyone who has ever written a script and subsequently dealt with anyone who calls himself or herself a “producer” will feel the absolute pain of Robert Wuhl’s increasingly cynical and bitter writer/director lead character. He aims to make a film that is beautiful, and that will provide meaning for a major loss in his life. In short, he wants to make “art”.

The long line of actresses, investors, and producers he deals with all claim to want the same… Only they all seem to know exactly what to do to make the project “better” and won’t give him the money, agree to star in it, or help produce his dream project unless he agrees with them.

Mistress, like The Big Picture, is a cautionary tale about compromise, but a much more realistic and hopeless one. The addiction and obsession required to even attempt to make a film in Hollywood is portrayed unflinchingly in Mistress. Wuhl (in an extraordinarily underrated performance), can’t stop trying to make his film, no matter how much it kills him to keep going through the process and the disappointment over and over again.

In the most bitter and heartbreakingly honest moment in the movie, Wuhl’s wife (played by a very tired and empathetic Laurie Metcalf) tells her husband what he and probably ninety nine percent of filmmakers trying to make it in Hollywood need to hear: “Your film could have been beautiful, but no one wants to see it… You have to stop dreaming.”

The tragedy, and the humor, of the film comes from the simple fact that he can’t. As Wuhl asks, “What else am I here for…?” Mistress is the perfect representation of the punishment of the Hollywood dreamer who just can’t stop dreaming.


7. Tropic Thunder (2008)

Tropic Thunder

Bitter satire disguised as a comedy romp. After a string of safe Hollywood hits, Ben Stiller got his voice and his balls back in this 2008 comedy about a group of spoiled actors who think they’re making a war movie, but are actually forced to survive in the middle of a real life war zone.

Tropic Thunder shows Hollywood for the true insane asylum it is: producers who would rather see their movie stars tortured and killed than lose their investment, diva sycophantic directors who can’t keep their productions in order, agents who are more concerned with up to date jetliners than the safety of their clients, and, of course, actors who will go so far as to change the pigment of their skin to prove to the world the importance of their craft (and their desire to stay on top of the fame game).

Tropic Thunder makes fun of just about everything there is to make fun of in Hollywood, and it has a grand time in doing so. Tom Cruise’s turn as a huge-handed, foul mouthed sociopathic producer is about as good and demented as a Hollywood satire can get… And is probably the most realistic part of the movie, too.


6. L.A. Confidential (1997)

L.A. Confidential

1950’s Hollywood was a beautiful time. Men were rugged and upright. Women were beautiful and mysterious. Movie stars were gods. Heroes and villains were clearly defined, especially in the movies. The surface of things is where the beautiful people lived, showed off, and did all the wonderful work they shared with the world. Curtis Hanson’s noir masterpiece based on James Ellroy’s novel, LA Confidential, shows the underbelly of old Hollywood.

For the all the surface beauty and lights, Hollywood was a town built on corruption, lies, prostitution, murder, and robbery. Ellroy’s characters are cogs in the machine underneath the glamorous surface that keep its illusion alive. The cracks in the streets, the hookers, the crooks, the crooked cops… They’re all presented as necessary evils that keep this particular world running but that nobody seems to want to talk about or admit. LA Confidential exposes and explores these elements with expert precision.

Though the movie is filled with multi-dimensional and complicated characters that combat the time period’s surface ideals, it is truly Russell Crowe’s performance and character that makes LA Confidential come to life and rise above most other films of its kind.

In Crowe, we have a leading man who is well-intentioned, but who is also inherently flawed and corrupt in how he dispenses his own brand of justice. He’s a Hollywood anti-hero represented in a time of plain Hollywood heroes. He is the dark side of justice and the dark side of Hollywood… And he’s also just a complete badass who makes most Hollywood tough guys look like Ghandi.