Hollywood seems like a pretty fascinating place to work. So fascinating, in fact, that those who work there still feel compelled to tell stories of what it’s like. There are countless movies set in Hollywood that give a glimpse at the magic of making movies.
These movies can focus on the actors, the director, the writers or countless other people who help bring a movie to life. While it might be a dream of many to make a career like this, these movies don’t always paint it in the most flattering light. However, many movies also celebrate what a joy it can be as well. Here are the best movies about working in Hollywood.
The Artist
The Artist looks at the bygone era of silent films in the early days of Hollywood, cleverly presenting itself as a silent film at the same time. The film follows a big star who finds his celebrity fading and future uncertain as the silent film begins to go out of style.
The story is a familiar one about how glory fades over time. The silent film effect might seem gimmicky, but it is actually used to tell an entertaining and moving story while also being a fun throwback to the kind of movies that made Hollywood.
Hail, Caesar!
The Coen Brothers clearly have a love for Hollywood of the past and they got a chance to pay homage and play around with a lot of it in Hail, Caesar!. The screwball comedy stars Josh Brolin as a Hollywood fixer who has to deal with a variety of situations like a hapless Western actor, a pregnant starlet, and a kidnapped leading man.
The Coens use this as an opportunity to make mini-movies from a variety of genres of the 1940s era, such as a sword-and-sandal epic, a prestige drama and a musical comedy to name a few. It is also a love letter to work in the business even if it isn’t always rewarding.
Tropic Thunder
Some of the best movies about Hollywood are the ones that poke fun at all the egos and delicate personalities involved. Tropic Thunder is a hilarious action-comedy about a group of spoiled and eccentric actors who are filming a Vietnam film and find themselves in a real battle.
The movie pokes fun at those who take movie making maybe a bit too seriously, especially Robert Downey Jr.’s outrageous performance as an actor whose method acting goes to offensive extremes.
Sullivan’s Travels
Sullivan’s Travels is a classic film from acclaimed director Preston Sturges about how it can be alright to embrace the fun in life through motion pictures. The story follows a director of escapist films who desires to make an “important film” so he sets out to live on the streets to get a better idea of real-world struggles.
The film is an entertaining road trip adventure with some genuine laughs and wonderful moments. It also features an interesting message about the importance of entertainment in the world.
Get Shorty
Get Shorty is a hilarious and fun comedy that combines the world of organized crime with the world of movie-making. John Travolta stars as Chilli Palmer, a movie-loving wise guy who becomes involved in producing movies. Soon he finds that this line of work can be equally dangerous.
The movie has a lot of fun with the idea that everyone thinks they can make movies and the ones who actually do might not be the best qualified. It is a light and fun ride featuring plenty of colorful characters and a great performance from Travolta.
Barton Fink
The Coen Brothers take another look at Old Hollywood in Barton Fink, and this time it’s a much more cynical look. John Turturro stars as the titular characters, a celebrated New York playwright who reluctantly takes a job in Hollywood writing a wrestling movie.
The film makes Hollywood feel like it’s filled with nothing but arrogant people and blowhards. Barton might think he’s representing the common people, but he sees himself as more important than them. Meanwhile, the studio executive is a vulgar loudmouth who throws his weight around like a thug.
Tootsie
We’ve often seen movies about actors struggling for their big break. Tootsie is a comedy about one actor willing to go to great lengths to get a part. Dustin Hoffman stars as a dedicated thespian who poses as a woman to get a part on a popular sitcom.
Despite how silly the premise solid, Tootsie is an incredibly smart comedy filled with hilarious performances from its talented cast. It is also a nice look at those who have a genuine passion for what they do even if they aren’t always given the opportunity.
Once Upon A Time In Hollywood
Quentin Tarantino’s love of Hollywood is legendary and very evident in all of his films. Once Upon a Time in Hollywood is his very personal love letter to the movie business in 1969 in the midst of cultural change. The movie follows actor Rick Dalton and his best friend and stuntman as they try to find their way in New Hollywood.
The movie is a fun look at how the business can change and how some find it difficult to adjust to that change. It also brings Hollywood of this era alive in such an engrossing and entertaining way.
Sunset Boulevard
Sunset Boulevard is a classic noir film from the great filmmaker Billy Wilder. It tells the story of a Hollywood screenwriter who develops a strange relationship with a reclusive former leading lady of the silent film era who yearns to return to the spotlight.
Gloria Swanson, whose career somewhat mirrors that of her character, is iconic and unsettling as the former celebrity. It is a haunting look at what fame can do to a person and what happens when that fame disappears.
The Player
A commonality in films about Hollywood seems to be that the people in charge of the studios are not depicted in the most positive of ways. Robert Altman’s The Player puts one such character in the center of the story and it’s still not a flattering portrait of a studio man.
The satire is a witty and clever look behind closed doors of how films get made by the big decision-makers. The movie is packed with stars appearing in small cameos which adds to the authentic feel of the movie. It doesn’t make Hollywood look like the most amazing place in the world, but it does make it entertaining to watch.
