Hollywood loves Hollywood. Remember when Birdman won Best Picture over Boyhood in 2015? There’s no denying that Alejandro González Iñárritu’s black comedy deserved its trophies that year, but it was also no surprise that a Broadway vs. Hollywood story beat out a small film like Boyhood—which happened to be incredibly unique in the way it was authentically filmed over 12 years in order to capture its main character’s growth. It would have been a treat to see Richard Linklater’s film take the top prize that year, but it was no match for a movie about movies.
If you love films, it can be fun to see those that take us behind the scenes. And with meta features like Being the Ricardos and Licorice Pizza still hitting the masses, it’s clear this unique sub-genre of cinema isn’t going anywhere. And it’s certainly been around for some time, dating back to short films by Charlie Chaplin and even Buster Keaton’s Sherlock Jr. (1924), whose protagonist is a projectionist dreaming himself into a movie. Here are some of the top movies of all time that happen to be themselves about Hollywood and the biz.
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10 The Player (1992)
Via Fine Line Features
Here, we follow the life of a Hollywood studio executive (Tim Robbins), and all seems mundane in his day-to-day of rejecting film scripts—until he accidentally kills an aspiring screenwriter who he believes is sending him death threats. The Player is a 1992 American satirical black comedy directed by the late, great Robert Altman and also starring Greta Scacchi, Fred Ward, Whoopi Goldberg and Peter Gallagher. It has many film references and Hollywood inside-jokes, with more than 60 celebrities making cameos. Altman stated in the DVD commentary that the film “is a very mild satire.” Production-wise, it even has an impressive long take to open the film—conveniently tracking characters who converse about the famous tracking shot from “Goodfellas.” This is just one example of The Player’s metaverse, which is relentlessly entertaining throughout. The film received three nominations at the 65th Academy Awards and won two Golden Globes.
MOVIEWEB VIDEO OF THE DAY
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9 Adaptation (2002)
Columbia Pictures
Talk about meta: this 2002 comedy-drama is brought to you by the iconic duo behind Being John Malkovich, director Spike Jonze and writer Charlie Kaufman. First of all, its protagonist’s name is none other than Charlie Kaufman (played by the excellent Nicolas Cage). Kaufman has said he based Adaptation on his struggles to adapt Susan Orlean’s 1998 nonfiction book The Orchid Thief. It involves elements adapted from the book plus fictitious elements, including Kaufman’s twin brother (also credited as a writer for the film). It culminates in completely invented elements, including versions of Orlean and John Laroche—her book’s protagonist—three years after the events of The Orchid Thief.
Adaptation was praised for its direction, screenplay, humor, and the performances of Cage, Chris Cooper and Meryl Streep. It received awards at the 75th Academy Awards, 60th Golden Globe Awards, and 56th British Academy Film Awards, with a never-better Cooper deservedly winning the Oscar for Best Supporting Actor.
8 8½ (1963)
Via Columbia Pictures
81⁄2 follows a harried movie director who retreats into his memories and fantasies. Guido, who is trying to relax after his last big hit, can’t get a moment’s peace, with folks who have worked with him in the past constantly looking for more projects. He wrestles with his conscience, but is unable to come up with a new idea. While thinking, he starts to recall major events in his life, as well as all the women he has loved (and left). It’s an autobiographical film of acclaimed auteur Federico Fellini that focuses on the trials and tribulations of filmmaking. 81⁄2 took home the Academy Award for Best Foreign Language Film and is now considered to be one of the greatest and most influential films of all time.
7 Sullivan’s Travels (1941)
Via Paramount Pictures
In Sullivan’s Travels, a Hollywood director sets out to experience life as a homeless person in order to gain relevant life experience for his next movie. He is a successful, spoiled and naive director behind fluffy films with a heart of gold, and decides that he wants to make a film about the troubles of the downtrodden poor. Much to his producers’ chagrin, he sets off in tramp’s clothing with a single dime in his pocket to experience poverty firsthand—and he feels the sting of reality.
Sullivan’s Travels received mixed reviews upon its release, but over time, the film’s reputation improved tremendously. In 1990, it was selected for preservation in the U.S. National Film Registry by the Library of Congress and, like 81⁄2 , is now considered one of the most influential films in cinematic history.
6 Inglourious Basterds (2009)
Via The Weinstein Company
“Sooound good?” In Nazi-occupied France during World War II, a plan to assassinate Nazi leaders by a group of Jewish U.S. soldiers coincides with a theater owner’s vengeful plans for the same. The young Jewish refugee had witnessed the slaughter of her family by Colonel Hans Landa (an out-of-nowhere, spectacular Christoph Waltz) years earlier. After narrowly escaping, she plots her revenge several years later when a German war hero takes an interest in her and arranges an illustrious movie premiere at the theater she now runs. With the promise of every major Nazi officer in attendance, the event catches the attention of the “Basterds”, a group of Jewish-American guerrilla soldiers led by the ruthless Lt. Aldo Raine (a scene-stealing Brad Pitt).
Inglourious Basterds grossed over $321 million in theaters worldwide, making it Tarantino’s highest-grossing film to that point, until the alt-universe hit was surpassed in the box office by Django Unchained (2012) and Once Upon a Time in Hollywood (2019). The film received widespread acclaim, with praise for Tarantino’s screenplay, direction and performances. For his role as Landa, Waltz rightfully won Best Supporting Actor at all the major award shows.
5 Mulholland Drive (2001)
Universal Pictures
After a car crash on the winding Mulholland Drive renders a woman amnesiac, she and a perky Hollywood-hopeful (Naomi Watts in a career-making turn) search for clues and answers across Los Angeles in a twisting venture beyond dreams and reality. Fate has other plans in store for Watts’ character, setting the stage for life-altering experiences with the unexpected, indecipherable and unknown.
The American-French co-production was originally conceived as a television pilot, and a large portion of the film was shot in 1999 with David Lynch’s plan to keep it open-ended for a potential series. After viewing Lynch’s cut, however, TV executives rejected it. Lynch then provided an ending to the project, making it a feature film. The half-pilot, half-feature result, along with Lynch’s characteristic surrealist style, has left the general meaning of the film’s events open to interpretation. In true Lynchian fashion, the acclaimed filmmaker and artist has declined to offer a full explanation of his intentions for the narrative.
4 Boogie Nights (1997)
New Line Cinema
“I am a star. I’m a star, I’m a star, I’m a star. I am a big, bright, shining star.” Dirk Diggler from Torrance has a unique gift that he wants to use for movies—pornographic movies, that is. Back when sex was safe, pleasure was a business and business was booming, an idealistic producer (Oscar-nominee Burt Reynolds) aspires to elevate his craft to an art when he discovers a hot young talent. Eddie is young, good looking and plenty of libido to spare. Using the screen name Dirk Diggler, he quickly rises to the top of his industry winning awards year after year. Drugs and ego, however, come between Dirk and those around him, and he soon finds that fame is fleeting.
Boogie Nights is an expansion of Anderson’s short film The Dirk Diggler Story (1988) and features an all-star cast that also includes Julianne Moore, Don Cheadle, John C. Reilly, William H. Macy, Philip Seymour Hoffman and Heather Graham. It premiered at the Toronto International Film Festival in 1997 and was theatrically released later that year, garnering critical praise. It was also nominated for three Academy Awards, and the film’s soundtrack has also received acclaim.
3 All About Eve (1950)
20th Century Fox
In All About Eve, one of two masterpieces from the year 1950, we find Eve Harrington (Anne Baxter) waiting backstage to meet her idol, the talented but aging Broadway star Margo Channing (Bette Davis). It seems innocent enough as Eve explains that she has seen Margo in every performance of her current play. Margo and her friends take Eve under their wing, but only theater critic Addison DeWitt (George Sanders) sees through Eve’s evil plan, which is to take Margo’s parts—and her fiancé (Gary Merrill) as well.
Critics and academics have discussed the various themes in the film over the years, such as the antagonism that existed between Broadway and Hollywood at the time. Roger Ebert once compared the aging actress plot line to another industry-centered gem, Sunset Boulevard, which came out the same year and, wouldn’t you know it, is next on our list…
2 Sunset Boulevard (1950)
One could argue: the less you know about this film before going in, the better. But here it is: It’s Hollywood of the 50s, where we meet an obscure screenplay writer (William Holden) struggling to sell his work to the studios. He’s also riddled with debts and thinking about returning to his hometown to work in an office. While trying to escape from his creditors, he has a flat tire and parks his car in a decadent mansion on Sunset Boulevard. He meets the owner and former silent-movie star Norma Desmond (Gloria Swanson), who lives alone with her butler and driver. The delusional Norma believes she will return to the film industry and proposes that Joe to move to the mansion and help her in writing a screenplay for her comeback. Before long, the small-time writer becomes her lover and gigolo. What a premise!
Praised by many critics when first released, Sunset Boulevard was nominated for 11 Academy Awards (including nominations in all four acting categories) and won three. It’s often ranked among the greatest movies ever made. As it was deemed “culturally, historically, or aesthetically significant” by the U.S. Library of Congress in 1989, Sunset Boulevard was included in the first group of films selected for preservation in the National Film Registry.
1 Singin’ in the Rain (1952)
Metro-Goldwyn-Mayer
What a decade—the top three films on our list all come from the 1950s. Those not familiar with this Gene Kelly classic might be surprised to hear that Singin’ in the Rain is indeed a film about the biz (and not just a beloved musical). Here we follow a silent film star who falls for a chorus girl just as he and his delusionally jealous screen partner are trying to make the difficult transition to talking pictures in 1920s Hollywood. Similar plot points can be found in the 2011 Oscar-winner The Artist—an honorable mention when compiling this list—but Singin’ in the Rain takes the cake for spawning such a unique storyline.
Those not familiar might also be surprised to hear that Singin’ in the Rain was only a modest hit when it was first released, despite the awards and nominations it soon received. However, it has since achieved legendary status by contemporary critics and is ranked as the fifth-greatest American motion picture of all time by AFI.
