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'Singin' in the Rain' (1952) -

Gene Kelly plays a popular silent movie star who started out as a tap dancer and stuntman, and Debbie Reynolds plays a chorus girl who catches her big talking-picture break. It's a love letter to the Hollywood musical and one of its finest exampled, and it also serves as a time capsule for what Hollywood was once like.

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'Saving Mr. Banks' (2013) -

This period drama unearths the backstory behind how Walt Disney (played by Tom Hanks) was determined to make a 1964 live-action big-screen musical out of the popular storybook 'Mary Poppins,' and how he courted (and emotionally manipulated) a reluctant P.L. Travers (played by Emma Thompson) for the rights to release his adaptation of her works.

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'Ed Wood' (1994) -

Tim Burton directed this comical but sensitive biopic about the eccentric and eventual cult filmmaker Ed Wood and his big ambitions that lacked mostly (but essentially) talent.

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'The Disaster Artist' (2017) -

This hilarious biopic, starring James Franco as eccentric actor-director Tommy Wiseau, tells the mysterious story of how 'Room,' one of the worst films to ever play on the big screen, was made. It's an ode to the film's cult fame, which rings out in Hollywood to this day with consistent showings where the audiences know all the words.

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'Adaptation' (2002) -

A screenplay by Charlie Kaufman directed by Spike Jonze, 'Adaptation' is for the writers of Hollywood as it follows a screenwriter (Nicolas Cage) desperately trying and failing to adapt 'The Orchid Thief' by Susan Orlean for the screen.

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'Once Upon a Time in Hollywood' (2019) -

Quentin Tarantino's imaginative version of Hollywood in 1969, when the murderous Manson family was on the prowl, earns an obvious place on this list. The film centers on two friends, a one-time TV Western star whose career is dying, and his stunt double who is a war vet skilled in hand-to-hand combat.

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'Sunset Boulevard' (1950) -

This noir is a cynical take on Hollywood and sees a deadbeat screenwriter, played by William Holden, stumble across a forgotten silent star, played by Gloria Swanson, who hires him to rewrite a script for her. The film features shots of the Hollywood Hills, backlots, and homes, as well as cameos from the likes of Buster Keaton and Cecil B. DeMille (“All right, Mr. DeMille, I'm ready for my close-up,”).

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'Dolemite Is My Name' (2019) -

This high-energy film is a celebration of the self-made Blaxploitation pioneer Rudy Ray Moore and his groundbreaking kung-fu action hero named Dolomite, played by Eddie Murphy.

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'The Aviator' (2004) -

Leonardo DiCaprio plays the eccentric billionaire Howard Hughes in this Martin Scorsese-directed biopic about the aviation pioneer who was also a movie producer and the director of the 1930 film 'Hell's Angels.' The film touches on everything from Hughes' OCD to his relationship with Katharine Hepburn.

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'Pain and Glory' (2019) -

Famed Spanish director Pedro Almodóvar selected Antonio Banderas to play a version of himself on screen, a depressed aging filmmaker in declining health who has just had one of his earlier films reissued and who looks back to see how he got to where he is now.

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'Mulholland Drive' (2001) -

If you can get past the disturbing dive into David Lynch's mind, it's considered one of the best movies ever made about Hollywood. “You feel the history of Hollywood in that road,” Lynch said about the street of the title. Naomi Watts plays an aspiring actress struggling to claim her space in an industry full of women that eerily look just like her.

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'Hollywoodland' (2006) -

Adrien Brody plays a detective who examines the mysterious death of real-life actor George Reeves (played by Ben Affleck), star of the 1952 television series 'Adventures of Superman,' though the detective gets dangerously caught in a web of lies involving big studio exec Eddie Mannix's wife Toni (played by Diane Lane).

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'Gods and Monsters' (1998) -

This drama, set in the '50s, stars Ian McKellen as James Whale, the director of the '30s horror classics 'Frankenstein' and 'Bride of Frankenstein.' It tells the story of Whale's last days, how he lived with a housemaid who didn't approve of his homosexuality, and how he befriends his handsome gardener (played by Brendan Fraser).

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'The Artist' (2011) -

This French comedy-drama in the style of a black-and-white part-talkie follows an egomaniacal film star who develops a relationship with a rising young actress during Hollywood's silent era.

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'Chaplin' (1992) -

Though it was a box-office bomb about one of Hollywood's earliest megastars, Robert Downey Jr.'s portrayal of Charlie Chaplin remains the biggest draw. Chaplin recounts his journey from a poverty-stricken childhood to worldwide success.

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'La La Land' (2016) -

Set in Los Angeles, a jazz pianist falls for an aspiring actress, but their passions and career successes conflict with their love for each other.

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'Barton Fink' (1991) -

This film from the Coen brothers is set in 1941 and follows delusional New York playwright Barton Frink (John Turturro) as he goes to LA to become a screenwriter while trying to hold on to his perceived creative integrity as he comes to face with the hellish reality of Hollywood.

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'Hail, Caesar!' (2016) -

It's interesting to see how the Coen brothers' take on Hollywood changed from 'Barton Fink' and the Golden Age to the McCarthy era. The film shows a day in the life of a fictionalized version of infamous film producer and "fixer" Eddie Mannix (Josh Brolin) as he tries to keep Capitol Pictures' affairs in order.

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'Boogie Nights' (1997) -

The adult film industry is still a part of the film industry! Paul Thomas Anderson shows a rare look at the behind-the-scenes drama of it. Mark Wahlberg plays a high-school dropout who gets wrapped up in his alter-ego, drugs, murder, and the difficulty of passing one's peak.

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'Hitchcock' (2012) -

To look behind the curtains of Hollywood is to take a hard look at one of Hollywood's most famous directors. Anthony Hopkins plays Alfred Hitchcock in this biopic as he and his wife Alma Reville (Helen Mirren)  work behind the scenes of his 1959 horror classic 'Psycho.' It's important to note, however, that this film was criticized for its failure to portray the way Hitchcock was said to habitually sexually harass his leading ladies.

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'The Player' (1992) -

One of the best Hollywood satires out there, Tim Robbins stars as a studio exec who controls what films get made each year, but whose power is challenged when an up-and-coming story exec is hired.

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'The Bad and the Beautiful' (1952) -

Taking place over an 18-year period, roughly from 1934 to 1952, this melodrama tells the story of a film producer who has risen from rags to riches in the industry by using and manipulating various people, but who finds that he soon needs the help of those he's betrayed.

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'Bowfinger' (1999) -

This hilarious film written by and starring Steve Martin follows a talentless filmmaker who fails to land a major star (Eddie Murphy) for his bargain basement film and thus decides to shoot the film around the star without his knowledge.

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'Somewhere' (2010) -

Coming from a veritable Hollywood royal herself, Sofia Coppola explores the story of an adequately famous but deeply unsatisfied movie star (Stephen Dorff) whose daughter (Elle Fanning) is the only enlivening thing around him.

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'S.O.B' (1981) -

This satire is actually based on star Julie Andrews' relationship with director (and husband) Blake Edwards after he tried to cut her good-girl image down with their 1970 flop 'Darling Lili.' But the film follows a suicidal film producer who decides to make a softcore porn musical that requires his actress wife (played by Andrews) to reveal her breasts on screen.

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'The Big Picture' (1989) -

Kevin Bacon stars as a film student who, still on a high from winning an award for a short film of his, wrongly thinks he's ready to hop into Hollywood. He leaves his values behind in exchange for success, and we get to see a satirical story with truth at its root.

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'Sullivan's Travels' (1941) -

This comedy pokes fun at the Hollywood elites by following a popular filmmaker who wants to make socially relevant dramas instead of his usual fluffy comedies, so he takes off on a trip to find the depressed, unemployed, and unglamorous people of America.

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'Hollywood Shuffle' (1987) -

This highly entertaining film from Robert Townsend stars Townsend himself across a collection of vignettes based on his own struggles as a Black actor trying to make it in Hollywood, but who is often pigeonholed into stereotypes.

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'State and Main' (2000) -

David Mamet's criminally underseen and hilarious film follows a big Hollywood production that faces bigger obstacles when forced to relocate to a small town. It's a highly entertaining peek at drama between the cast and crew that occurs while actually in production.

Sources: (Den of Geek) (GoldDerby) (IMDb) (IndieWire)

See also: Hollywood scandals that history forgot

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