Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Movies about making movies are always an interesting idea – and these films show how to do the concept the right way.



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Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Movies can get meta very quickly when they revolve around the film industry, because showing a bunch of people making movies draws attention to the artifice of cinema. Filmmakers usually try to distract audiences from this artifice with immersive visuals and captivating stories, but drawing attention to it can lean the other way and wink to the viewer by outright acknowledging the fourth wall.

Quentin Tarantino put his stamp on the curious “movies about making movies” subgenre back in 2019 (which seems like decades ago) with Once Upon a Time in Hollywood, but there are plenty of other great examples.

10 Once Upon A Time In Hollywood (2019)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Tarantino blended facts with fantasy in Once Upon a Time in Hollywood, which gives Sharon Tate a fictional neighbor in the form of fading TV western star Rick Dalton. The 1969 Manson Family murders marked a major turning point in the film industry, and that turning point provided the backdrop of Tarantino’s sun-drenched cinematic odyssey.

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Leonardo DiCaprio, Brad Pitt, and Margot Robbie anchor the movie with terrific performances, while the loose plotting of Tarantino’s script gives it the laidback feel of a hangout movie.

9 Bowfinger (1999)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Steve Martin stars in Bowfinger as an unscrupulous producer who will go to any lengths necessary to get his movie made. With a sci-fi script called Chubby Rain, he assembles an amateur cast and crew and tells them movie star Kit Ramsey – played by Eddie Murphy – is attached to play the lead role.

In reality, Bowfinger’s plan involves following Ramsey around L.A. with hidden cameras and playing out the scenes around him to trick him into starring in the movie. Part of the scheme involves casting Kit’s dim-witted twin brother Jiff, also played by Murphy.



8 Singin’ In The Rain (1952)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

While it’s best remembered for its musical numbers, Singin’ in the Rain is really about the transition between silent films and “talkies.” An on-screen duo who are always paired up face challenges when their latest movie is retooled as a musical and only one of them has a good enough singing voice.

It’s a definitive story about the film industry’s struggle to adapt to sound. Gene Kelly and Debbie Reynolds both give phenomenal performances.

7 Adaptation (2002)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

When Charlie Kaufman was hired to turn Susan Orlean’s The Orchid Thief into a movie, he struggled so much with it that he ended up writing a movie about his struggle to turn the book into a movie instead.

Nicolas Cage stars as a fictionalized Charlie Kaufman and his entirely fictional twin brother Donald in Adaptation, a satirical breakdown of the conventions of Hollywood screenwriting.

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6 Dolemite Is My Name (2019)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

In addition to being a beloved standup comic and earning the nickname “the Godfather of Rap,” Rudy Ray Moore embodied the spirit of independent filmmaking. After creating the Dolemite character and conceiving a blaxploitation homage to bring him to the screen, Moore took a shoestring budget and a barebones crew and helmed an overnight sensation.


Eddie Murphy’s biopic of Moore, Dolemite is My Name, was the perfect vehicle for the iconic comedian’s Hollywood comeback. Like many comedic movies, it was overlooked by the Academy.

5 Get Shorty (1995)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Adapted from the Elmore Leonard novel of the same name, Get Shorty stars John Travolta as mob enforcer Chili Palmer, who goes to Los Angeles on a job and decides to leave the criminal lifestyle behind to make a killing in the film industry.

The movie draws hilarious parallels between the tactics used by Hollywood producers and the tactics used by gangsters. Gene Hackman, Rene Russo, and Danny DeVito all give strong supporting performances.

4 Tropic Thunder (2008)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

When Ben Stiller was a kid and his dad appeared in a war movie, he noticed that all his co-stars returned from the set with the mentality of a soldier returning from an actual warzone. This planted the seeds for Tropic Thunder, a hysterical satire about a bunch of unwitting Hollywood movie stars being sent into an active warzone to shoot a Vietnam epic.

From Tom Cruise’s giant-handed studio executive character barking down the phone at a warlord to Robert Downey, Jr.’s method actor character having a breakdown and reverting back through his various Oscar-winning roles, Tropic Thunder is a hilarious lampoon of the movie business.

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3 Sunset Boulevard (1950)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

One of the most acclaimed film noirs ever made, Billy Wilder’s Sunset Boulevard sees a delusional aging movie star hiring a screenwriter to mount her comeback project.

Opening with one of the most iconic shots in film history, Sunset Boulevard is anchored by incredible performances by William Holden and Gloria Swanson as Joe Gillis and Norma Desmond, respectively, while Erich von Stroheim gives a memorable supporting turn as Desmond’s loyal butler.

2 The Player (1992)

Once Upon A Time In Hollywood & 9 Other Great Movies About The Film Industry

Robert Altman brought a pitch-black comedic edge to The Player, his satire of the film industry. Tim Robbins plays a studio executive who starts receiving death threats and murders the aspiring screenwriter he believes to be responsible.

This is a quintessential movie for film lovers, as it’s filled with A-list cameo appearances, references to existing movies, and in-jokes about the business.

1 8½ (1963)

When Federico Fellini was between projects and struggling with director’s block, he decided to just make a movie about a filmmaker who’s between projects and struggling with director’s block.

One of Fellini’s greatest works (and that’s saying a lot), 8½ jumps between minimalist scenes expressing Fellini’s disillusionment with the film industry and mesmerizing dream sequences that exemplify what the art of cinema can do at its best.

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