The Five Best “Hollywood on Hollywood” Movies

Nick Nunziata

The only thing that Hollywood likes doing more than patting itself on the back is to satirize itself. Early filmmakers got meta before meta was even a twinkle in the eye of the jerk who coined the phrase. “Movies about the movie business” is a storied sub-genre filled with classics and bombs, sly satire and slapstick, action and inaction. In many ways it’s a microcosm of everything that makes the film industry so alluring and maddening at the same time. And nearly everyone has at one point or another tossed their hat into the ring. From David Mamet’s excellent State and Main to Preston Sturges’ seminal Sullivan’s Travels to George Huang’s acerbic Swimming With Sharks, there are numerous great takes on the subject of Hollywood.

Here are five we think will hit the spot in preparing you for this week’s release of Hail, Caesar!, the Coen brothers’ latest comical microscope on the business — starting with another Coen brothers film, Barton Fink.

Barton Fink (1991)

Barton Fink is not an easy watch. Set in 1941, the picture displayed here from the Coen brothers concerns a successful New York playwright named Barton Fink who abandons everything when offered a contract in Hollywood. Barton finds himself completely out of his element as he checks into his hotel, deals with his new boss at Capitol Pictures, and meets the seemingly unstable neighbor with whom he shares a wall. Very quickly he realizes that his crusade to create a theater for the common man must be shelved when he’s forced to make a movie about wrestling, and soon his world begins to fall apart. The Coens pull no punches with their characters here, and the heaviest load is carried by lead actor John Turturro. His delivery in the film is the stuff of neurotic nightmares as he deals with ego, insecurity, depression, angst, fear, murder, and writer’s block. Barton Fink is fascinating and surreal and terrifying, especially if you’re self conscious. [Andrew Hawkins]

The Player (1992)

Robert Altman turns his satirical eye on the cutthroat world of Hollywood deal-making in this dark slice of insider baseball. Studio executive Griffin Mill (Tim Robbins) has been receiving death threats from a jilted screenwriter and sets out to discover who this disturbed individual is. You would think that the story is a simple thriller set in backlots and soundstages, but Altman and writer Michael Tolkin (adapting his own novel) subvert everything you expect. The film is more of a wry dissection of studio politics and the business of moviemaking rather than a paperback mystery. What’s doubly impressive is that the film never loses its bite while still delivering the kind of cookie-cutter popcorn flick that mass audiences crave. It’s also loaded with an insane number of celebrities cameoing as themselves, so it functions as a fun bit of, “Hey, look it’s…” as well. The Player is an acerbic necessity for those who want to see what life is like in the world where dreams are made. Expect the mandatory happy ending, but don’t expect it to make you happy. [Drew Dietsch]

Ed Wood (1994)

Hollywood is a cruel place, especially for creators who don’t want to sacrifice their artistic vision due to studio interference. That’s what makes Ed Wood one of the most uplifting pictures about Tinseltown ever made. Based on the life of the “worst director of all time,” Ed Wood follows the infamous filmmaker through the production of three of his films: Glen or Glenda?, Bride of the Monster, and Plan 9 From Outer Space. The level of energy and positivity Johnny Depp brings to the titular character is so infectious that you can’t help but fall in love with the guy, but it’s Martin Landau as Bela Lugosi who steals the show. Seeing the once-great horror star after he’s been chewed up and spit out by the system is heartbreaking, and Landau brings endless amounts of pathos to the Dracula actor. Ed Wood is a movie about embracing your oddness and letting it flourish, even when those in power tell you it’s a hindrance. Hollywood is full of underdogs and weirdos, and no film celebrates those people more than Ed Wood. [Drew Dietsch]

Adaptation (2002)

Charlie Kaufman has a way of finding conduits into storytelling that no one else can, and there’s no better example of that than Adaptation. Based on the seemingly unfilmable Susan Orlean novel The Orchid Thief, Kaufman and director Spike Jonze turn the entire thing on its ear with a story that is surreal, hilarious, heartbreaking, and awe-inspiring — sometimes all at once. Nicolas Cage hasn’t been better than here, where he plays Kaufman and his fictitious twin brother as they negotiate the terrain of screenwriting. Chris Cooper steals every scene he’s in, and Meryl Streep does what Meryl Streep does better than anyone in the business. It’s an unforgettable film, and when it revisits the set of the filmmakers’ earlier Being John Malkovich it somehow pulls off the “movie within a movie within a movie” thing as if it weren’t impossible. This is a cinematic high-wire act and it works like a charm. [Nick Nunziata]

Tropic Thunder (2008)

The brilliance of Tropic Thunder is that it doesn’t make fun of just Hollywood actors and directors but the whole damn system. Ben Stiller’s film is an action-comedy first and foremost, but it’s also a sly takedown of the hubris and silliness of the entertainment industry. These people take their craft and talent so seriously, and when you take a step back, it’s all just painfully funny. Tropic Thunder is dumb and loud and violent and silly, but it’s also quite clever and biting, like all great satire should be. [Brandon Marcus]

One could easily list another 15 films that execute this satirical theme well, but these five are all fingers on the same hand. They are movies that show the beauty and beast of the film industry in a way that makes it look easy. And it really isn’t. Hail, Caesar! looks to be the next in the line, and we couldn’t be more excited.

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Nick Nunziata
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