Hollywood likes to reflect itself in both movies and TV series. As a result, people interested in the fate of famous actors as well as the inner goings of Hollywood can find multiple movies focused on this topic. A lot of them take on the task to uncover the darker, less glorious side of Hollywood, but some are more optimistic.

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Whatever the case, the best movies about Hollywood have it all - from a compelling story to a strong cast that wouldn’t be out of place in classic Hollywood movies as well. And since filmmakers have been making this type of movie for decades, they also offer a unique view of old Hollywood.

7Sunset Boulevard (1950)

Sunset Boulevardis one of the greatest classics of all time. It’s also a highly bitter story that shows how far ambitions can drive people, right into the arms of tragedy. The movie centers on a young ambitious screenwriter who builds a relationship with an aging former star, but everything goes south eventually.

The movie has excellent actors in the leading parts, William Holden and Gloria Swanson, as well as former legends in cameos, such as Buster Keaton.Sunset Boulevardis hailed as one of director Billy Wilder’s best movies thanks to the realistic cynicism with which it approaches Hollywood and its people.

Sunset Boulevard 1950

6Singing In The Rain (1952)

Even thoughSinging in the Rainpremiered only two years afterSunset Boulevard, tone-wise, the movie couldn’t be different. It takes place during the 1920s when silent movies gradually made their transitions to talking pictures. That’s something not every actor was happy with or even could work with because some of the previously successful actors had voices that just didn’t work for the audience.

Singing in the Rainstars Gene Kelly and Debbie Reynolds, and it’s ultimatelya feel-good captivating movie with musicthat lightens up the whole story. The most iconic scene features Gene Kelly dancing and singing in the rain, but the movie has many memorable moments.

Singing in the Rain 1952

5Chaplin (1992)

Long before he becameIron Man in the MCU, Robert Downey Jr. was nominated for an Oscar for his role as Charlie Chaplin in this biopic.Chaplinis enjoyable even for those viewers who haven’t seen any of Charlie Chaplin’s movies, and it might very well persuade them to try some of his work.

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The movie shows how Chaplin rose to stardom and focuses both on his work life and private life. Thanks to Downey Jr.’s performance and the captivating story,Chaplinis a must-watch for all people who enjoy stories about old Hollywood and its greatest icons.

4Ed Wood (1994)

Ed Wood is universally known as the worst movie director of all time. Whether that reputation’s warranted or not, there’s no denying that his movies were shot too fast and in amateurish conditions. Yet in the Tim Burton movie withJohnny Depp playing the titular role, Ed Wood ultimately comes across as a sympathetic person, somebody who genuinely loves movies and wants to do what he enjoys.

Unfortunately for him, the world seems to stand in his way.Ed Woodshows what happens when excitement meets lack of talent and is one of the most civil Tim Burton movies, filled with great actors and offering a mixture of humor and drama.

Chaplin 1992

3The Artist (2011)

If the audience wants to watch a modern silent movie, thenThe Artistis the best choice. It even won an Oscar for the best picture. It focuses on two actors, one of whom is established and successful and a young woman who gradually rises to stardom.

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The movie’s beautiful black and white pictureas well as the catchy soundtrack immediately draw the audience in. The acting performances and story then keep them hooked.The Artistnot only captures Hollywood and its people well, but it also offers a unique experience so different from the majority of 21st-century movies.

2La La Land (2016)

Ryan Gosling and Emma Stone appeared as a duo multiple times in the movies but the Oscar-winning musicalLa La Landis their most popular cooperation. Stone stars as an aspiring young actress Mia andGosling as a talented musician Sebastian. They get together but their paths eventually separate.

What makes this movie fascinating is its portrayal of the toll ambitions and dreams have on relationships between people, even those who love each other. As a result,La La Landis less sweet and more bittersweet than many people might expect from an American musical about Hollywood.

Ed Wood, Johnny Depp

1Once Upon A Time In Hollywood (2019)

One of the latest Hollywood-centered movies even has Hollywood in its title. The almost three-hour movie isthe love letter Quentin Tarantino wrote to old Hollywood. It works with a mixture of fictional characters (the two main heroes played by Leonardo DiCaprio and Brad Pitt), and real-life actors and other Hollywood personalities.

Even though the movie lacks a coherent, tight storyline, and functions more as a chain of loosely connected smaller stories, its atmosphere, and the star-studded cast are enough to offer a memorable experience, and maybe even make the audience nostalgic for the 1960s.

The Artist 2011

La La Land

Leonardo DiCaprio and Brad Pitt in Once Upon A Time… In Hollywood (2019)