10 Brilliant Movies About Movies Every Cinephile Should Watch

1. Singin' in the Rain (1952)

• Directors: Stanley Donen and Gene Kelly
• Writers: Betty Comden and Adolph Green

An American classic and one of the best musicals of all time, it's a hilarious look at Hollywood as it transitions into the talkies from silent pictures.

There are so many iconic song-and-dance numbers inside this movie that make you want to sing along. And I love how it humorously portrays the challenges faced by silent film stars adapting to the new technology and working with the studio. The movie offers a lighthearted yet insightful look at a pivotal moment in cinematic history, and it shows the biz in magical ways.

2. Sunset Boulevard (1950)

• Director: Billy Wilder
• Writers: Charles Brackett, Billy Wilder, and D.M. Marshman Jr.

One of the greatest film noir movies of all time, it's a dark and cynical masterpiece. Its themes unpack faded glory and obsession.

The film follows a struggling screenwriter who becomes entangled with a delusional former silent film star desperate for a comeback. They both want to be relevant in Hollywood and need each other to work out all the problems in their lives. It's a powerful and unsettling critique of the cruelty of the Hollywood machine and how it will kill you.

3. The Player (1992)

• Director: Robert Altman
• Writer: Michael Tolkin (based on his novel)

With probably one of the best opening scenes of all time, Robert Altman's sharp and satirical film is a brilliant send-up of the Hollywood studio system.

The film follows a studio executive who finds himself in hot water after killing a disgruntled screenwriter and trying to get away with it, all while trying to run the day or day of his studio.

The cast is full of giantly famous people who are in on the clever, self-referential narrative.

4. 8½ (1963)

• Director: Federico Fellini
• Writers: Federico Fellini, Tullio Pinelli, Ennio Flaiano, and Brunello Rondi

It's not just Hollywood that makes movies; there are a ton of foreign filmmakers who also love making movies about movies. And Federico Fellini made an incredible one.

This is a surreal and introspective movie that's a deeply personal exploration of a film director's creative crisis. The film blurs the lines between reality and fantasy as a famous Italian director struggles with his next project, his personal life, and his own artistic anxieties all at once. It's a thematically rich meditation on the pressures and complexities of the creative process and of filmmaking in general.

5. Day for Night (1973)

• Director: François Truffaut
• Writers: François Truffaut, Jean-Louis Richard, and Suzanne Schiffman

This movie is so funny. I actually think it should be required viewing for anyone who wants to work on movies. It is François Truffaut's love letter to the collaborative spirit of filmmaking. And in a world where things can go wrong, everything does.

The movie follows the cast and crew of a fictional film as they navigate the ups and downs of production that are so relatable.

6. Ed Wood (1994)

• Director: Tim Burton
• Writers: Scott Alexander and Larry Karaszewski

This film is probably in my top ten of all time. In a world where everyone is desperate to tell their stories, Ed Wood did that. But his movies were never embraced, and he wound up a tragic but also somehow inspirational person for filmmakers everywhere.

Tim Burton's affectionate black-and-white biopic tells the story with nuance and grace. And at its center is a heartfelt performance from Johnny Depp. The film celebrates Wood's passion and perseverance in the face of critical disdain and shoestring budgets.

7. Adaptation (2002)

• Director: Spike Jonze
• Writer: Charlie Kaufman (and "Donald Kaufman," his fictional twin)

This is a movie I think every screenwriter needs to watch. It really unpacks what we go through and the incessant internal monologue that drives us. Also, the jealousy, anger, loneliness, and every other emotion I feel in every waking second.

The movie follows a fictionalized version of Kaufman as he struggles to adapt a non-fiction book about orchids into a screenplay. It's brilliantly meta and mind-bending.

8. Once Upon a Time in Hollywood (2019)

• Director: Quentin Tarantino
• Writer: Quentin Tarantino

Leave it to Tarantino to have an opus about what it means to be in Hollywood. His nostalgic and revisionist take on late 1960s Hollywood follows a fading television actor and his stunt double as they navigate the changing landscape of the film industry.

It's wildly relatable, even though it's set in a world a little more fantastic and just than our own. The film is a vibrant and detailed love letter to a bygone era.

9. Babylon (2022)

• Director: Damien Chazelle
• Writer: Damien Chazelle

I think this movie was unfairly maligned in its time and has only gotten better with age.

Damien Chazelle's epic tale of ambition and excess is set in 1920s Hollywood during the transition from silent films to sound. It's sort of like an R-rated Singing in the Rain.

We follow the rise and fall of multiple characters, from a silent film star to a young ingenue, capturing the debauchery and dizzying heights of early Hollywood.

10. American Movie (1999)

• Director: Chris Smith
• Writer: Chris Smith

This beloved documentary is a must-see for everyone who loves the filmmaking process. It chronicles the struggle of aspiring independent filmmaker Mark Borchardt as he attempts to complete his short horror film, Coven.

It's a raw and deeply moving portrait of passion, friendship, and the relentless pursuit of a creative dream against all odds in the American Midwest.

Once you finish watching, you're going to want to watch it again immediately afterward.

Summing It All Up 

This might be my favorite subgenre of all time. I know this can be pretentious and even boring to some, but Hollywood is where I have always wanted to be and work. These movies, even the darker ones, show dreams coming alive and offer the promise of a life we've all dreamed of since we were young.