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The Best Movies About Hollywood

As the home of American cinema, Hollywood populates the public's imagination with epic dramas, larger-than-life action flicks, gut-busting comedies, and more. But Hollywood isn't just a place where dreams are made — it's a dream unto itself. A gorgeous part of Los Angeles, filled with creatives of all stripes looking to connect with others and bring their vision to life? That's juicy stuff. No wonder there are so many movies about the town where movies are born.

Some of the most impactful, important, and acclaimed films of all time, in fact, have been about the movie-making business. Moreover, the genre is a lot wider than you'd expect: David Lynch fever dreams and revisionist history, courtesy of Quentin Tarantino, both fall under the umbrella of "movies about Hollywood." To help narrow it down, we're here to introduce you to the best movies about Hollywood ever made. Prepare to get stars in your eyes.

Once Upon a Time in Hollywood

2019's Once Upon a Time in Hollywood is a sprawling ode to movie magic, starring Leonardo DiCaprio as fading Western star Rick Dalton and Brad Pitt as Rick's hardworking stunt double, Cliff Booth. As audiences follow their antics and adventures across the Los Angeles landscape, they're also introduced to the real-life figure of Sharon Tate, played by Margot Robbie. Ultimately, Cliff and Rick end up involved in Sharon's journey, stumbling upon the Manson cult and eventually changing history on the night Sharon Tate was murdered. In Quentin Tarantino's world, she survives — and even invites Rick over for drinks.

A wry, sharply written and expertly-directed romp that both critiques Hollywood and presents it with love, Tarantino's homage to the 1960s ultimately earned multiple wins and several nominations at the 2020 Academy Awards, including one for Best Picture. If you're looking for a love letter to some of Hollywood's most fascinating years, Once Upon a Time in Hollywood is a perfect choice.

La La Land

At this point, 2016's La La Land may be remembered most for the infamous mix-up at the 2017 Academy Awards, in which presenter Faye Dunaway mistakenly announced that the film was that year's Best Picture winner, even though Barry Jenkins' Moonlight actually won. However, the film did take home a number of other awards, including Best Director for Damien Chazelle and Best Actress for its leading lady, Emma Stone, proving that it's much more than just the subject of an embarrassing Oscar night gaffe.

La La Land tells the story of Mia (Stone) and Sebastian (Ryan Gosling), an aspiring actress and struggling jazz musician respectively, who meet in Los Angeles and fall hard for each other. However, after a lengthy relationship, they start to realize that their dreams may ultimately keep them apart. With original songs composed by celebrated composer Justin Hurwitz and winning performances from both Gosling and Stone — marking their third collaboration after Crazy, Stupid, Love and Gangster Squad – La La Land is a dreamy ode to Hollywood's classic musicals. It's a nostalgic project, full of nods to beloved films and eras, yet it still manages to break new ground. From its gripping love story to its mesmerizing song and dance numbers, La La Land simply has it all.

Singin' in the Rain

One of the most beloved films about Hollywood in cinematic history, Singin' in the Rain has something for everybody: Astounding dance sequences, a clever narrative, and jokes that still hold up today. Released in 1952, the film focuses on Hollywood in the 1920s, as the industry made the tricky transition from silent films to "talkies" — the first-ever spoken film, 1927's The Jazz Singer, is name-checked. It stars Gene Kelly as dashing movie star Don Lockwood, Jean Hagen his narcissistic and irritating leading lady Lena Lamont, Donald O'Connor as Don's loyal best friend Cosmo Brown, and a young Debbie Reynolds as aspiring actress Kathy Selden.

As Don and Lena try to navigate the new cinematic landscape with Kathy and Cosmo's help, they figure out that they need to turn their disastrous new romance, The Dueling Cavalier, into a musical. However, there's one big problem: Lena has a terrible singing voice. After using dubbing to feature Kathy instead, it looks like the film is saved ... right up until everything comes to a head in the most dramatic way possible. From cheery sequences like "Make 'Em Laugh" and "Good Morning" to the exultant title track, Singin' in the Rain is still one of the cleverest, most incisive films ever made about Hollywood.

Hail, Caesar!

If you're a fan of Joel and Ethan Coen's goofier fare, you'll definitely love Hail, Caesar!, a bright-eyed tribute to Hollywood's seamy underbelly. This 2016 film tells the story of real-life figure Eddie Manix, a 1950s Hollywood "fixer" played by Josh Brolin. He is tasked with finding out what caused Baird Whitlock, a vapid, A-list actor played by George Clooney, to disappear during the filming of a biblical epic. As he investigates further, Eddie realizes that Baird has somehow ended up in the clutches of a nefarious Communist group, and must navigate his way through Hollywood's dark side to get him back on set.

In typical Coen brothers fashion, the cast is incredibly stacked: Besides Clooney and Brolin, the movie features huge names like Channing Tatum, Scarlett Johansson, Ralph Fiennes, Tilda Swinton, Frances McDormand, and Jonah Hill, among others. If you're in the mood for a clever caper about Hollywood's seedy doings, Hail, Caesar! is a perfect choice for your next movie night.

The Artist

It might sound crazy that a silent film won Best Picture at the Academy Awards in 2011, but if you've seen Michel Hazanavicius' The Artist, you'll understand why. The Artist is the first (mostly) silent film to win the top prize since 1929's Wings achieved the same feat at the first Academy Awards, and the first entirely black-and-white movie to win Best Picture since 1960's The Apartment. The Artist uses its silent film styling to tell the story of George Valentin (played byJean Dujardin, who won the Academy Award for Best Actor that year), a silent film star who takes a chance on a young actress, Peppy Miller, played by Bérénice Bejo. Peppy's star begins to rise after Valentin gives her a role in one of his films ... but his own falls. Before long, only Peppy can save George from obscurity and despair.

Thanks to the charming chemistry between Dujardin and Bejo, as well as a brilliant script that balances dramatic story with light-hearted joy, The Artist is one of the best films ever made about the highs and lows of Hollywood. If you want to transport yourself to another era, The Artist is a perfect pick.

For Your Consideration

If you're a fan of Schitt's Creek and haven't seen any of Eugene Levy and Catherine O'Hara's other collaborations with director Christopher Guest, you'll definitely want to check out 2006's For Your Consideration. One of Guest's classic mockumentaries, For Your Consideration centers three actors — Marilyn Hack (O'Hara), Victor Allan Miller (Harry Shearer), and Callie Webb (Parker Posey) — on the precipice of winning major awards for their still-unfinished film, Home for Purim. However, upon further inspection, the film definitely doesn't seem award-worthy, thanks to its weirdly experimental director (played by Guest) and its hapless producer, Whitney Taylor Brown (Jennifer Coolidge), an heiress to a diaper fortune who knows nothing about the movie industry. Meanwhile, Victor's agent Morley Orkin (Levy) spends his time trying to get a higher salary for his star.

A sharp, witty look at the awards circuit, For Your Consideration is acerbic in all the right ways. Sure it's nice to see glittering odes to the Hollywood movie machine — but sometimes, you need something that rips into the industry's foibles. If you're in the mood for that sort of experience, this is the movie for you.

Sunset Boulevard

A classic film that explores the darker side of the industry, Billy Wilder's 1950 noir, Sunset Boulevard, is widely considered to be one of the most important movies ever made. The film stars Gloria Swanson as Norma Desmond, an aging silent film star who drags young, struggling screenwriter Joe Gillis (a flawless William Holden) into her attempts to revitalize her flagging career. As Joe tries to help Norma pitch her horribly written script about Salome, the two continually take advantage of each other, with Norma getting deranged beauty treatments and Joe manipulating Norma while secretly working on a script of his own.

Ultimately, the push and pull between Norma and Joe comes to a violent head. Even if you don't know how the film ends, you're probably familiar with the film's big closing line: "All right, Mr. DeMille, I'm ready for my close-up." No list of films about Hollywood would be complete without Sunset Boulevard, which manages to be right on the money more than 50 years after its debut.

Mulholland Drive

Director David Lynch is known for his fascinating, surreal work, including groundbreaking television shows like Twin Peaks and bizarre movies like Blue Velvet. Naturally, 2001's Mulholland Drive is no exception. Betty Elms (played by a sterling Naomi Watts), a struggling actress, is shocked to discover a mysterious woman named Rita in her aunt's apartment. Rita, who has just survived a terrible car accident on the titular road, remembers nothing of her past. Betty resolves to help her, but as she tries to uncover the mysteries of Rita's life, she finds herself embroiled in a series of events as  hallucinatory as they are horrifying.

Regarded as one of Lynch's very best works — which is a pretty high bar to clear — Mulholland Drive weaves a terrifying, twisted story fans are still puzzling over. For a wholly original take on Hollywood, look no further than Mulholland Drive – just expect to be left with more questions than answers.

A Star is Born

After years in Hollywood, Bradley Cooper made his long-awaited directorial debut with 2018's A Star is Born. He plays Jackson Maine, a faded rock star who revives his career with the help of Ally (played by Lady Gaga), a young singer he discovers at a drag bar. After inviting her onstage to sing, Ally's career takes off ... just as Jackson's begins to flag. As the two struggle to maintain a relationship in the public eye and make their respective careers work, Ally and Jackson fight, grow, and try to figure out what success in the entertainment industry really means.

A Star is Born is the third remake of the original 1937 film starring Janet Gaynor and Fredric March: 1954's version stars Judy Garland and James Mason, while 1976's stars Barbra Streisand and Kris Kristofferson. A Star is Born is clearly a timeless story, and Cooper and Gaga's addition to the tradition is just as worthy as its predecessors.

L.A. Confidential

Based on the novel of the same name, L.A. Confidential tells the story of a group of LAPD officers in 1953 who find themselves occupying the tense grey area between Hollywood power and police corruption. With a cast that includes Kevin Spacey, Kim Basinger, Guy Pearce, Russell Crowe, Danny DeVito, and James Cromwell, L.A. Confidential focuses on the career of Sergeant Ed Exley (Pearce), who, in a desperate attempt to live up to his late father's legacy within the LAPD, explores the darker side of Hollywood. In the meantime, his cohorts work with sleazy Hollywood bigwigs to further their own goals. As you might guess, things come to an explosive end.

Ultimately, the film served as an introduction for Pearce and Crowe, who were still relatively unknown in North America. Though it lost most of the Academy Awards for which it was nominated to Titanic, it still took home a statue for Best Adapted Screenplay and one for Basinger for Best Supporting Actress. A perfect example of neo-noir, L.A. Confidential is a gripping, intense story with plenty of twists to keep you guessing throughout the entire film.

Get Shorty

A rare film that blends thriller style with outright comedy, 1995's Get Shorty is based on Elmore Leonard's beloved novel of the same name. This film features John Travolta, Gene Hackman, Rene Russo, and Danny DeVito in a story about gangsters involved in the movie business. As Chili Palmer, Travolta plays a loan shark who picks up several odd jobs, including one in Los Angeles, where a failing Hollywood producer named Harry Zimm (Hackman) is hiding out from a casino manager to avoid paying a huge sum. As he gets deeper into Hollywood and tries to help Zimm with his script, Chili realizes just how corrupt Hollywood has become.

The film was ultimately so popular that it spawned a 2005 sequel, Be Cool, also based on one of Leonard's novels. Get Shorty remains a staple of both the gangster and the Hollywood genre. If you're looking for a clever, hilarious take on Hollywood's sleazy side, Get Shorty is definitely your best bet.

Ed Wood

It may seem counterintuitive that a director could strike gold by making a movie about one of the worst movies of all time, but somehow, Tim Burton and Johnny Depp won over audiences and critics alike with Ed Wood. Released in 1994, Ed Wood features Depp as the titular filmmaker, and focuses on some of his most infamous creations, as well as his relationships with real Hollywood stars like Bela Lugosi and Loretta King. In the end, Wood finally gets to make one of his best-known films, Plan 9 From Outer Space, even though the entire filming experience is an utter disaster.

Though the film flopped at the box office, it ultimately became a cult classic, even winning an Academy Award for Best Supporting Actor for Landau, who plays the legendary Lugosi. There's no question that Burton and Depp make cinematic magic together, and if you want to watch one of their earliest collaborations — which just so happens to also feature Sarah Jessica Parker and Patricia Arquette — you'll definitely want to check out Ed Wood.