Hollywood loves to make two things: money and movies about itself. Well, this September,Clerks IIIdid the latter. After surviving a heart attack,series mainstay Randal Graves unites his friendsto make a movie about Quick Stop.
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It’s not the first time writer-direction Kevin Smith has gotten meta. In one of the most memorable scenes fromJay and Silent Bob Strike Back,the title characters are extras on the set of the fictional movie:Good Will Hunting 2: Hunting Season.Smith follows a long tradition of comedies about movie-making, fromSingin' in the RaintoTropic Thunder. Here are some of those classics.
‘The Disaster Artist’ (2017)
The adaptation ofGreg Sestero’sbook of the same title was directed by and starredJames FrancoasTommy Wiseau– the “auteur” (to use the word loosely) who created the filmThe Room. The movie routinely shows up onworst movie listsbut has earned a cult following since its release in 2003.The Disaster Artistfollows Wiseau as he crafts his opus.
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From inspiration to funding to shooting to premiere, Franco’s film covers the entire movie-making process. It’s perhaps most memorable for its on-set antics, specifically Wiseau struggling to nail the infamous line: “I did not hit her. I did not. Oh hi Mark.” The movie is a blast and a crash course on how to make a terrible movie.
‘Tropic Thunder’ (2008)
A film crew is attempting to make a highly expensive Vietnam War film (thinkPlatoon,or that one section inForrest Gump),but the cast is out of control. To save the production, the actors dropped into the jungle with blank-filled guns and hidden cameras recording their every move. But instead of making a war epic, they’re dropped in an epic war.
Tropic Thundermay be the definition of a movie that couldn’t get made today. Released in 2008,Ben Stiller, Jack Black, and Robert Downey Jr….the latter of which appeared in blackface. But as dangerous as the material might be, the film succeeds and flourishes because of its relentless takedown of Hollywood stars and movie-making. The entertainment industry is always the butt of the joke – as it should be.

‘Singin’ in The Rain' (1952)
The one that started it all. Sure, the iconic film is the seminal film of Hollywood’s Golden Age of Musicals. But it may also be the greatest movie ever made about the transition from silent films to talkies.
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Everybody knows “Singin' in the Rain,” “Make ‘Em Laugh,” and “Good Morning.” But less discussed is the film’s sheer comedy, namely the scene that illustrates what happens when a movie’s sound isn’t mixed correctly. It’s no mistake the film stands at 16th onAFI’s 100 YEARS…100 LAUGHS list.
‘Boogie Nights’ (1997)
Paul Thomas Anderson’ssecond feature might not sound like an obvious inclusion, but sure enough, it’s all about the art of movie-making. In fact, a lot of the film takes place on set or is about making a movie, editing a movie, selling a movie, etc. WhileSingin’ in the Rainfocuses on the transition from silent movies to sound,Boogie Nightscenters on the porn industry’s transition from film to tape.
Boogie Nightsis harrowing filmmaking, and Anderson’s homage toScorsese, Altman,andDemme. But it’s also hilarious. From Reid’s hot tub poem to Dirk claiming he blocks his own scenes, the director’s script is as funny as any while also trojan-horsing an allegory for the corruption of New Hollywood in the late 70s.

‘Ed Wood’ (1994)
Some movies about Hollywood are about geniuses – tyrannical egomaniacs with singular visions. NotEd Wood.Tim Burton’s 1994 film follows Wood, a man legendary for being the worst director who ever lived. But the film doesn’t wallow in his failure or deride it for a cheap laugh. It enjoys the absurdity of his films and the unlikelihood of his talent with a warm generosity.
Much of the film takes place on set as viewers watch Wood assemble his little family, fromVampiratoTor JohnsontoBela Lugosi, who played the original Dracula. While similar to theDisaster Artistin some ways,Ed Woodis really about an open-minded, ambitious manwho loves to bring together discarded people…and is terrible at making movies.

‘Wag The Dog’ (1997)
To prevent the fallout of an election-year presidential sex scandal, a spin doctor brings in a top Hollywood producer to manufacture a fake war. Underneath the shell of a political satireWag the Dogis a good ol' fashioned movie about movies.
StarringDustin Hoffmanas the producer andRobert De Niroas the spin doctor, the movie tackles every part of the modern-day Hollywood procedure: producing an idea with a wide demographic appeal, marketing the story, and demanding credit when it succeeds. It’s a pitch-black rebuke of politics and Hollywood and a must-see cautionary tale about Hollywood filmmaking.

‘State and Main’ (2000)
Few films have Hollywood come out the other end looking like the land of dreams, andState and Mainis no exception. Writer-DirectorDavid Mamet’s2000 film follows a big Hollywood production that takes over a small town in Vermont.
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The production is supposed to be shooting a film called “The Old Mill.” There’s just one problem: the town’s mill burned down 100 years ago. Now, the writer (played by the latePhilip Seymour Hoffman) must devise a completely new script only days before principal photography. Filled with great performances and Mamet’s stellar writing,State and Mainis about all the nonsense that a Hollywood production goes through on a daily basis.
‘Real Life’ (1979)
Maybe the single funniest movie on this list isAlbert Brooks'1979 comedyReal Life. Brooks plays a fictionalized version of himself who wants to capture the life of a normal American family for one year. Naturally, Brooks can’t help but interfere with every stage of the production.
Real Lifeis a comedy classic. It opens with Brooks explaining the rigorous tests he’s devised for finding the most normal family in America. Then, the movie really gets going when he travels to Arizona to live with the Yeagers – the winning family. Over time, the production completely corrupts the thing it hopes to capture and sends Brooks into a fit of egomaniacal madness.

‘Official Competition’ (2022)
Released in 2022,Official Competitionis the most recent film featured here, the only Spanish-language movie, and the only one that portrays the more overlooked part of the filmmaking process: rehearsals.
The movie starsPenelope Cruzas a brilliant, yet eccentric director who demands that her two leads rehearse together weeks before production. One of the leads is a movie star played byAntonio Banderas. The other is a celebrated theater actor played byOscar Martinez, who provides the funniest scene in the film when he practices rejecting an Oscar in front of the mirror.