20. Trumbo (2015)
Bryan Cranston stars as famous screenwriter Dalton Trumbo, whose communist tendencies put a spanner in the works of his career. In response, Trumbo combats his blacklist placement by selling scripts on the black market.
As the writer behind epics likeSpartacus(directed by Stanley Kubrick) andExodus(directed by Otto Preminger), Trumbo’s predicament made him resort to writing scripts without any credits.
The nostalgic aesthetics of Hollywood’s golden age is contrasted by the political tension of America’s climate in Jay Roach’s drama (based on Bruce Alexander Cook’s 1977 biography.)
Related:The Best Screenwriters in Hollywood, Ranked
19. The Disaster Artist (2017)
It’s universally agreed thatThe Room(directed by Tommy Wiseau) is the worst film ever made. Wiseau’s bad script and bizarre acting makes for a film that’s so bad, it’s good.
Well, maybe not good, but definitely a cult classic. One that’s been repeatedly analyzed, mocked, and enjoyed—so much so that Hollywood went ahead and made a comedy-drama about the creation ofThe Room.
James Franco perfectly embodies Wiseau’s elusive persona, starring alongside his brother Dave Franco and best friend Seth Rogen.The Disaster Artistis surprisingly touching for a comedy about the strange world of Wiseau, presenting the niche subject to a wider audience.
18. Their Finest (2016)
Can propaganda ever be beautiful? Director Lone Scherfig thinks so. Set during the Second World War,Their Finesttakes a refreshing female angle that revamps the Ministry of Information’s morale-boosting war movies.
Whereas men want to tell a heroic tale of a fictional soldier, Catrin Cole (played by Gemma Arterton) fights to tell the true story of two brave sisters at Dunkirk.
From script to set, we witness the old-school ways of filmmaking that aided in the British war effort. Funny, charming, and surprisingly tragic at times,Their Finestis a finest piece of wartime cinema.
Related:The Best War Movies Based on True Stories and Real Events
17. Be Kind Rewind (2008)
InBe Kind Rewind, there are no A-list names or huge studio lots used for Mike and Jerry’s movie productions (played by Mos Def and Jack Black). Instead, it’s papier-mâché and a home video camera.
Not long after Mike is left to supervise for his boss’s failing video store, he accidentally wipes all the tapes. Well, technicallyhedoesn’t wipe them—a tin-foil-covered paranoid guy does.
Rather than admit defeat, the two decide to recreate all the store’s movies themselves. Because why not? Michel Gondry’s buddy comedy is full of nerdy fun while showing us that great films don’t have to come with a great price tag. All you need is some TLC.
16. Adaptation (2002)
Adapting a book into a screenplay is long, grueling work… something that Charlie Kaufman learned inAdaptation.
Nicolas Cage stars as both Charlie and his twin brother Donald (who’s a complete freeloader). Self-loathing anxiety, depression, and sexual frustration cloud Charlie’s ability to write, based on his own experiences with writers block.
Tasked with adapting the 1994 novelThe Orchid Thiefby Susan Orlean (played by Meryl Streep), Charlie’s life becomes inexplicably tangled in his work. Spike Jonze’s comedy-drama is a semi-biographical metanarrative, though the real story was likely less wild.
Related:The Best Movies About Hollywood, Ranked
15. Hugo (2011)
Strictly speaking, most ofHugodoesn’t deal with making movies—it’s primarily about a broken automaton. Hugo (Asa Butterfield) is a poor orphaned boy living in the walls of a Parisian train station and his goal is to fix the machine and see what it makes.
But when you dig deeper, cinema is secretly at the heart of the entire film. As it turns out, the automaton sketches scenes from George Méliès filmography. (George Méliès was a prolific French filmmaker of early cinema, played in disguise here by Ben Kingsley.)
You can tell there was a passionate auteur behindHugobecause of how eloquently Martin Scorsese captured the magic of filmmaking. We see Méliès’s clear glass production palace where “dreams are made”—because, for him, dreams and films were synonymous.
Related:The Best Movies Set in the 1930s (Great Depression)
14. The Artist (2011)
This black-and-white Oscar-winning film echoes the dawn of cinema through its silent approach to modern filmmaking. Like the silent films of old,The Artisthas practically no dialogue, relying on visual cues and dance routines.
The French movie, directed by Michel Hazanavicius, follows the film star George Valentin in 1927. At the premiere of his latest hit, he falls in love with the young Peppy Miller—and his life begins to unravel as “talkies” (i.e. movies with sound) are introduced.
Jean Dujardin and Bérénice Bejo star as the potential lovers andThe Artist,which received widespread critical acclaim.
Related:The Best Movies Set During the Roaring Twenties (1920s)
13. Get Shorty (1995)
Get Shortywas recently modernized into a successful TV series in 2017. Great as it is, the show doesn’t use any characters or events from the original novel by Elmore Leonard. Only the basic premise.
But back in 1995, Barry Sonnenfeld adapted that book into a slick 90s gangster comedy that compares Hollywood to the sleazy world of crime. Much as we love movies, he’s not completely wrong!
There’s a potent sense of irony running throughGet Shortyas it mocks its own creators. A star-studded Hollywood cast in an MGM production? Seems pretty hypocritical—but in a fun way.
12. Chaplin (1992)
The legendary Richard Attenborough tells the story of a cinematic legend—the one and only Charlie Chaplin—inChaplin. Chaplin wasn’t just an icon of his time, but influential throughout all of film history to this day.
Beginning his life in poverty, Chaplin was raised on theater. After a spell of sleeping on the streets, he joined Keystone Studios in 1913 and rose to fame with his persona of The Tramp.
Attenborough recounts the idol’s life—his wealth, his affairs, his films, and even his FBI run-ins. Robert Downey Jr. elegantly portrays the troubled star who, despite facing his share of tragedy, brought smiles and joy to thousands of viewers across the world.
11. Me and Earl and the Dying Girl (2015)
Me and Earl and the Dying Girlhonors the magic of cinema as much as any other film on this list. Even if they’re just home videos. Directed by Alfonso Gomez-Rejon, the comedy-drama puts a spin on the usual cancer movie.
When awkward teen Greg (played by Thomas Mann) is forced to befriend Rachel (played by Olivia Cooke), they come to form an unexpected bond. Oh, and there’s also Earl (played by RJ Cyler).
Greg and Earl have a history of making short parody movies, so they decide to make a film for Rachel, who’s diagnosed with leukemia. Old home-movie-style footage and fourth-wall breaks give some creative flair to this otherwise sad story, reminiscient ofBe Kind Rewind.
Related:The Best Movies About Cancer and Terminal Illnesses
10. Hail, Caesar! (2016)
Get ready for an all-star cast in the Coen brothers' musical comedyHail, Caesar!starring the likes of Josh Brolin, George Clooney, Channing Tatum, Scarlett Johansson, Ralph Fiennes, Tilda Swinton, Jonah Hill, Frances McDormand…we could go on and on.
But don’t just watch it for the famous faces! Watch it because it’s packed with good fun. Kidnapped stars and pregnant actors make hell for Hollywood fixer Eddie Mannix (played by Brolin), and we get to sit back and watch it all unfold.
It may not be the Coens' most critically astute movie, but it’s certainly worthwhile for when you’re looking for something a little lighter than, say,No Country for Old Men.
9. The Life Aquatic With Steve Zissou (2004)
Wes Anderson takes us out of the studio and onto the road (or sea) with this making-of movie. Steve Zissou isn’t a filmmaker so much as an ocean explorer who records his deep-sea findings via video.
Bill Murray is in practically every Wes Anderson movie, but here he gets to be the star of the film as the sarcastic, selfish, but ultimately lovable oceanographer Steve.
Steve’s documentaries used to be a hit, but now he’s a fading star with an estranged son. He decides to kill two birds with one stone and make a cinematic comeback while avenging his best friend’s death-by-shark with his latest documentary.
Related:The Best Movies About Sharks and Shark Attacks
8. La La Land (2016)
La La Landtook the public by storm in 2016, sweeping the Oscars despite the embarrassing Best Picture fiasco. Beloved celebrity duo Emma Stone and Ryan Gosling get their dancing shoes on for Damien Chazelle’s musical that even musical-haters can love.
Whimsical cinematography takes us on a journey through the Hollywood dream, where wannabe actress Mia (played by Stone) meets wannabe jazz musician Sebastian (played by Gosling).
La La Landtackles the idea of whether hard work is enough to turn your dreams into reality—but not in a cynical way. The awe and wonder of film sets and jazz clubs are fully appreciated, with an ending sequence that just might bring you to tears.
Related:The Best Movies About Jazz Music
7. The Aviator (2004)
The Aviatoris another biopic, although it isn’t strictly film-bound. It follows Howard Hughes as he spreads his eggs across many baskets, from business to aviation to movie-making.
Unfortunately, Hughes suffered with severe OCD that led his life downhill. Leonardo DiCaprio stars as the once-dazzling, charismatic genius who’s haunted by the invisible dust around him.
Martin Scorsese directs this nearly-three-hour epic that documents Hughes' rise and fall. He even color gradesThe Aviatorto match what would have been available on film at the time!
Related:The Best Movies and TV Shows About OCD Behaviors
6. The Souvenir (2019)
The Souveniris more than just a film about making films. Director Joanna Hogg takes an intricate look into issues of class, art, love, addiction, and adulthood.
Dreamily filmed with luscious vignette cinematography,The Souvenirfollows a shy film student who forms an intense—and at times toxic—relationship with a (slightly) older man.
As an A24 film, you can expectThe Souvenirto be an absolute gem of independent cinema, and Hogg certainly delivers. The acting is subtle and brilliant, the pacing is slow and lyrical. It’s also quasi-autobiographical of Hogg’s own time in film school.
Related:The Best Romance Drama Movies of All Time, Ranked
5. Barton Fink (1991)
Joel and Ethan Coen use their knowledge of the movie industry to bring us a slightly more acclaimed peek into Hollywood thatHail, Caesar!viaBarton Fink.
Period drama meets black-comedy meets psychological thriller in this tale of a playwright who turns to the big screen, played by John Turturro.
Ludicrous Coen-flavored events distract Barton’s ability to focus, and writer’s block plagues his creativity.Barton Finkis a borderline cult favorite for its sheer madness and intellectual humor, winning the Palme d’Or in 1991.
Related:The Best Movies About Writers, Authors, and Writing
4. The Fabelmans (2022)
It seems like there’s at least one Steven Spielberg movie that comes out every year. He’s one of the few filmmakers who can churn out a conveyor belt of movies without losing any of their soul.
Although a lot of Spielberg’s canon is self-reflective—with recurring themes of father-son relationships and childhood wonder—The Fabelmansis the first film that’s literally about himself.
Spielberg’s semi-autobiographical tale is half about his filmmaking hobby as a kid and half about his dysfunctional family (namely his parents). And yes, you can expect the usual Spielberg family magic here!
3. Singin' in the Rain (1952)
It’s hard not to read the title ofSingin' in the Rainwithout a bit of sing-song in your voice. In this classic film, Gene Kelly swings around a lamppost in one of cinema’s most iconic scenes, while the rest of the cast splash through an encore of familiar tunes.
But what are they all singing in the rain about? Set in the 1920s after the revolutionary release ofThe Jazz Singer, Monumental Pictures (a metatextual stand-in for MGM) is forced to change their newest silent movie into a “talkie” to keep up with the times.
Singin' in the Rainoffers a rose-tinted view of Hollywood at the dawn of its Golden Age. It was made only a decade after its end, so you can still feel the residue of gold in the air!
Related:The Best Jukebox Musical Movies of All Time, Ranked
2. 8½ (1963)
Federico Fellini’s meditative comedy-drama8½is highly conscious of its own story, as Italian filmmaker Guido Anselmi (Marcello Mastroianni) tries to navigate director’s block during his latest sci-fi production.
Anselmi’s movie is partially based on himself, but nothing about it feels quite right. Also, he’s a terrible person.
8½is essentially a private monologue made external, stroked with brushes of spirituality, existentialism, nostalgia, and genius. It’s honestly one of the best movies about making movies, period.
Related:The Best Classic Old Movies Everyone Should See, Ranked
1. Sunset Boulevard (1950)
Billy Wilder’s fusion of black comedy and film noir madeSunset Boulevardan industry-defining movie. It’s even named after the major street that runs through Hollywood itself, and it features a cameo from silent film legend Buster Keaton.
Joe Gillis (William Holden) is struggling to write films at the same time that Norma Desmond (Gloria Swanson) is struggling to find them. The former starlet’s career is waning, so she hires Joe to write a script that’s specifically for her.
You know those films that Congress deems as “culturally, historically, or aesthetically significant”?Sunset Boulevardwas one of the first ones to be picked. If that doesn’t qualify it as the best movie about making movies, then I suppose no movie deserves the title.
Related:The Best Film Noir Movies of All Time, Ranked
