/Answers: The Best Movies About Making Movies

James Franco The Disaster Artist

Every week in /Answers, we attempt to answer a new pop culture-related question. In this edition, we celebrate The Disaster Artist by asking “What is your favorite movie about making movies?”

Ben Pearson: Singin’ in the Rain

As someone with an unabashed appreciation for big, bright, Technicolor crowd-pleasers, Singin’ in the Rain is my favorite movie about filmmaking. There are undoubtedly cooler or sexier choices in this category, but this is not only one of the best musicals of all time, but one of the best American films ever made – period. Stanley Donen and Gene Kelly’s riff on Hollywood in the late 1920s is one of the first films I saw that offered a detailed look behind the curtain of making movies, but even as it demythologized the actual process of filmmaking, it still manages to suck you in with its glamorous allure and effortless style. 

Practically everything about this movie is perfect: the structure (that flashback scene detailing how Don and Cosmo broke into the industry and how Don met Lina is masterful), the production design, and even when the movie dips into outright fantasy, it still manages to retain a cinematic weight because of Kelly’s physicality and the jaw-dropping work of the film’s dancers. Kelly, Debbie Reynolds, and Donald O’Connor are pitch perfect in the lead roles, and Jean Hagen practically steals the whole movie with her Oscar-nominated performance as Lina Lamont. The songs – though nearly all of them had previously appeared in other movies before they were popularized here – run the gamut of catchy, memorable, silly, emotional, and toe-tapping. If all that weren’t enough, the movie is often laugh-out-loud funny, especially during the disastrous desynchronized test screening of The Dueling Cavalier (the movie within the movie). A wonderful comedy, a momentous musical, and a straight-up classic, Singin’ in the Rain puts a smile on my face every time I watch it.

Ethan Anderton: Tropic Thunder

Take Three Amigos and mix it with Apocalypse Now and you get Tropic Thunder, the funniest movie about making a movie, which actually ended up being about the making of the most expensive fake true war story ever.

For my money, Tropic Thunder is one of the best comedies in this century so far. The assembly of talent across the board is incredible. Rarely do comedies get such a star-studded group of people together and create something worthwhile. But this is a movie that has Ben Stiller, Robert Downey Jr., Jack Black, Tom Cruise, Matthew McConaughey, Danny McBride, Steve Coogan, Nick Nolte and Bill Hader. That’s an amazing cast, though in retrospect, I wish there were some recognizable women involved in this movie.

Anyway, Tropic Thunder effortlessly skewers the making of blockbusters, celebrity star power, awards season, and everything that has to do with Hollywood. Hell, this movie even has some hilarious fake trailers and advertisements before the story kicks into gear in order to give us background on each of the key players starring in the movie within the movie and sending up the tropes of action movies, studio comedies, celebrity endorsements and Oscar contenders.

But my absolute favorite part of Tropic Thunder is the character who Tom Cruise plays. Les Grossman is a mix of the angriest studio executives working in Hollywood. Covered under make-up and wardrobe that makes him unrecognizable, Tom Cruise delivered one of the best performances of his career. The scene embedded never fails to make me laugh, especially when he says, “Okay, Flaming Dragon, fuck face. Why don’t you take a step back and literally FUCK YOUR OWN FACE!” I hope Tom Cruise lives forever.

Hoai-Tran Bui: Sunset Boulevard

Sunset Boulevard is so much more than a Gothic Hollywood noir. It’s a blistering takedown of the studio system that values youth and beauty over everything else, a harrowing tragedy about an older woman obsessed with the past, and a love letter to the Hollywood screenwriter. As “big” as Gloria Swanson’s Norma Desmond is — and she swallows up the screen as both the tragic figure and the monster that Hollywood created — it’s often forgotten that the main character of Sunset Boulevard is William Holden’s Joe Gillis.

A cynical screenwriter who has sold his soul to the moviemaking machine, Joe plays a thankless role in and outside of the context of the film. Holden’s straight man is often forgotten in the face of Swanson’s delirious scene-chewing, and Joe is fated to be forgotten as the victim and enabler of Norma’s delusions. But director Billy Wilder, who began his career as a screenwriter, makes sure to paint Joe and his ilk with a sympathetic eye, condemning Hollywood and its prioritization of formula over creativity. Joe is one of the “cogs” in the Hollywood machine, but the pictures couldn’t be made without him. As a screenwriter, he plays as an important part in films as the director, the crew, the star — and though our eyes are drawn to the fame-obsessed Norma, it is only through Joe’s sacrifice that she can be made “big” again. “Audiences don’t know somebody sits down and writes a picture,” Joe bemoans in the film. “They think the actors make it up as they go along.”

Sunset Boulevard is often brought up as the macabre foil to the many starry-eyed depictions of Los Angeles as the city of dreams, where fame and stardom can be achieved if you just try hard enough. But as much as it is a condemnation of Hollywood and how fame poisons its denizens, Sunset Boulevard is also a surprisingly warm depiction of the little people who work below the line. Just don’t get involved with any washed up movie stars.

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