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The Top 10 Films About Hollywood

By Martin Keady · March 17, 2015

No other art-form does “self-referential” as well as cinema. That is because for all the appeal of the “auteur” theory (the idea that films are essentially made through the vision of one individual) cinema is essentially a collaborative process, and it is certainly more collaborative than most art-forms. Consequently, while it might not be very exciting to see a film about someone writing, painting or composing (i.e. working on their own in a room), it is fascinating to see a group (or, on occasion, a whole army) of people working together and inevitably falling out, falling in love and falling in and out of bed together.

Similarly, while there are several fine films about the delights of indie film-making (notably Tom DiCillo’s hilarious Living in Oblivion) or foreign language filmmaking (notably Francois Truffaut’s marvellous Day For Night), most of the great films about filmmaking are about cinema’s capital city, Hollywood (and Los Angeles in general). Even now, in the 21st century, Hollywood remains the most lucrative and productive film industry in the world, attracting film-makers from all over the world, and consequently it is a natural setting for stories about the “seventh art-form.”

Here are the Top 10 Films about Hollywood.

 

10. The Last Tycoon (Directed by Elia Kazan, 1976)

So many movies about Hollywood are revenge-tragedies, or revenge-fantasies, usually featuring a disgruntled screenwriter who somehow seeks vengeance against his or her unfeeling bosses. The Last Tycoon is a variation on this theme, as it is based on the great F. Scott Fitzgerald’s last and unfinished novel, which was a semi-fictional, semi-autobiographical account of his own unhappy experiences in Hollywood.

The titular “Tycoon” is Monroe Stahr, a successful studio boss played by Robert De Niro who is financially and artistically successful, but personally bereft; devastated by the loss of the only woman he had ever truly loved, he finds himself obsessed with another young woman who reminds him of her. She becomes the one thing, or rather person, he cannot have and, distracted by his longing for her, he gradually loses control of the studio.

The Last Tycoon is an elegy to a Hollywood that was already long-gone by the 1970s, when the film was made, but its legacy remains, particularly in one scene that may just be the single best scene about film-making ever made, in which De Niro attempts to explain to a truculent theatre director, played by Donald Pleasance, exactly how movies work. He literally acts out, in silent movie-style, the scene he describes, in the process showing exactly how the strange and nebulous art of screenwriting (an art that even the great F. Scott Fitzgerald could not master) works.

[youtube https://www.youtube.com/watch?v=vqrU8KK3inc]

 

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9. Swimming With Sharks (Directed by George Huang, 1994)

The film may not have actually coined the term, “Swimming With Sharks,” but it certainly popularized it, until it became the perfect catch-all description of working in Hollywood: exciting but dangerous, and potentially fatal. It is a classic “kidnapping gone wrong” movie of the kind beloved by the Coen Brothers (as they admit themselves, so many of their films, from Raising Arizona to Fargo to The Big Lebowski are “kidnappings gone wrong”), but in this instance there is a Hollywood setting, as a young assistant, played by Frank Whaley, ends up kidnapping and torturing his abusive boss, Kevin Spacey (in arguably his greatest screen performance not to win an Oscar), in order to teach him a lesson about humility. It is a wonderfully dark and cynical movie, no more so than in its stunning, surprising ending, where the audience learn the true meaning of the movie’s title: it is possible to swim with sharks, but it is much easier if you become one yourself.

[youtube https://www.youtube.com/watch?v=nTBBQQRE0Z8]

 

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8. The Player (Directed by Robert Altman, 1992)

“The comeback” is one of the story-types beloved of Hollywood and the story behind the making of The Player is one of the great Hollywood comebacks, as the film marked the triumphant big-screen return of one of the greatest American directors, Robert Altman, after a 1980s largely spent making TV movies, and led to the second great period of his career (after his glorious 1970s), which included films such as Short Cuts and Gosford Park.

The Player, based on the novel of the same name by Michael Tolkin (who also co-produced and wrote the screenplay for it), is the ultimate Hollywood revenge fantasy, as a studio executive finds himself being stalked by a writer, apparently because he had rejected one of his pitches for a movie. The exec, superbly and nervously played by Tim Robbins, believes that he has found his stalker, and accidentally kills him, only to discover later that he has killed the wrong man. In fact, the real stalker, having learned of the exec’s murder of an innocent man, ultimately blackmails him into “greenlighting” his movie.

The “film within a film” in The Player is particularly memorable. Named Habeas Corpus, it is supposedly a “no-star, no-bullshit” crime drama, “with echoes of Kurosawa.” In the end, of course, it becomes a star vehicle (for a suitably be-vested Bruce Willis) with a risible and tacked-on happy ending. In this way, The Player shows how so often in Hollywood good, indeed high-minded intentions end up being transformed into bad (but often commercially successful) films.

[youtube https://www.youtube.com/watch?v=HpDDTS08wPs]

 

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7. Swingers (Directed by Doug Liman, 1996)

Swingers is much closer to the reality of most Hollywood lives than that depicted in most meta-movies (movies about movies), telling the story of a group of struggling young actors who are so desperate for work that they literally dream of donning a set of big ears and “playing” Mickey Mouse at Disneyland. Written by Jon Favreau, and starring Favreau himself and a young, slim and genuinely hilarious Vince Vaughn, Swingers is based on their own experiences as struggling actors dreaming of the kind of “big break” that, ironically, Swingers actually ended up being for them. From the pastiches of other movies, including Reservoir Dogs and Goodfellas, to the fabulous screenplay that combines Shakespearean quotations (“What’s past is prologue”) with its own instant-classic catchphrases (“You’re so money!”), Swingers remains by far the best thing that Favreau, Vaughn and director Liman have ever done, proving another Hollywood (and indeed universal artistic) truism: it is when an artist is on the outside, with their face pressed against the window of a restaurant as their more successful peers feast within, that they often produce their best work, and they can spend the rest of their supposedly more successful careers trying to reignite that initial, inimitable spark.

[youtube https://www.youtube.com/watch?v=nWCct8XbQD0]

 

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6. Singin’ In The Rain (Directed by Gene Kelly and Stanley Donen, 1952)

One of the great joys of compiling these cinematic “Top 10s” is the prospect of creating the perfect double bill: those movies that cry out to be seen together, so beautifully do they complement each other. Perhaps the greatest cinematic double bill, and certainly the greatest meta-cinematic (cinema about cinema) double bill is Singin’ In The Rain and The Artist (No.5 on this list, below). Of course, with these two it is ironic to say that they “cry out” to be seen together, because they are both about silent movies and the enormous difficulty that the stars of those movies experienced when they were literally trying to make themselves heard in the new age of sound.

In Singin’ In The Rain, the major obstacle facing the silent movie stars is the harsh, unattractive nature of their speaking voices, particularly that of the supposed leading lady, played by Jean Hagen, who has to have her voice dubbed over by an unknown stage actress, played by Debbie Reynolds, who is also her rival for the affections of the leading man, played by Gene Kelly. The famous, fabulous ending of the film shows how Kelly finally reveals the truth about Hagen’s character by literally “raising the curtain” on her, Wizard of Oz-style, while she is supposedly singing, to show that the true singer is Reynolds. It is a wonderful, self-referential image about the power of cinema (and indeed all forms of “show business”) to simultaneously tell and hide the truth.

That tension is evident throughout the film, from Gene Kelly’s opening reminiscences about his early days in movie making (claiming that he always tried to maintain his “dignity” even as he had to resort to ever more menial tasks, first as an extra and then as a stuntman) to the extraordinary scene in which Kelly, Reynolds and Kelly’s sidekick try to “rewrite” the disastrous period drama that they have made, The Duelling Cavalier, into an all-singing, all-dancing comedy, The Dancing Cavalier.  It is perhaps the most brilliant sequence on film that shows how Hollywood really is the “dream factory,” somewhere that dreams (in the form of movies) are literally made and, if necessary, recut, repackaged and remade.

[youtube https://www.youtube.com/watch?v=36QiuRc_3I8]

 

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5. The Artist (Directed by Michel Hazanavicius, 2011)

The Artist is the great foreign film about Hollywood. Set in the silent era, it is, of course, largely silent itself and its few spoken lines are in English. Nevertheless, it was a French film made by a French director and is ultimately about the experience of foreigners in Hollywood, particularly how hard they found it to effect a successful transition from the universality of the silent era (when what someone sounded like, i.e. their accent, didn’t matter) to the very particular nature of the sound era (when it very much mattered what someone sounded like, to the point of destroying their career if they didn’t sound right). In that vein, the ending of The Artist is one of the all-time great movie endings, subtly turning the audience’s expectations on their head; it is probably the most obvious twist in all of cinema, but it is none the less one of the most satisfying.

[youtube https://www.youtube.com/watch?v=OK7pfLlsUQM]

 

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4. Barton Fink (Directed by the Coen Brothers, 1991)

As someone who was actually nicknamed “Martin Fink” by a friend because of my love for this movie (and because I’m an even more unsuccessful screenwriter than Barton), I can personally testify to its strange, unsettling genius. It is one of the great “screenwriter” movies, showing how a successful New York playwright (allegedly based on the great Clifford Odets) is slowly driven mad in a dilapidated Hollywood hotel by the demands of his producer and his inability to write a good wrestling movie. (Incredibly, wrestling movies were big business in 1940s Hollywood).

In his desperation to learn how to write a wrestling movie, Barton enlists the help of his next-door neighbour at the hotel, Charlie Meadows, a door-to-door salesman who had been a successful amateur wrestler himself. Of course, this being Hollywood, nothing is as it seems, and “good ol’ Charlie” turns out to be a psychopath, “Mad Man Mundt,” who, after killing the legendary writer who Barton befriends (Frasier’s John Mahoney playing a character allegedly inspired by William Faulkner), eventually turns on Barton himself.

The tagline for Barton Fink was “Between Heaven and Hell, There’s Always Hollywood,” and it is a telling one. According to traditional Christian belief (and it is still the belief of the Catholic church today), what actually lay “Between Heaven and Hell” was Purgatory, the terrible limbo-like state where sinners were condemned to reflect upon their sins (often without even realising what their sins are). The Coen Brothers may be Jewish but their Hollywood, as depicted in Barton Fink, is a truly purgatorial state, in which writers churn out pointless, indeed largely unread, scripts on battered old typewriters, and, like the original inhabitants of Purgatory, dream endlessly of escape – even to hell itself.

[youtube https://www.youtube.com/watch?v=WK0WjWlVO9w]

 

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3. The Day of the Locust (Directed by John Schlesinger, 1975)

The original novel (of the same name) that The Day of the Locust is based upon is probably the great novel about Hollywood. It was written by Nathanel West in 1939, just before his death, and was based on his own experiences as a novelist who had reluctantly become a struggling screenwriter. However, unlike so many stories and movies about Hollywood written by struggling screenwriters, the hero of the novel, Tod Hackett, is not a writer but a set designer who, in true Hollywood tradition, dreams of being an artist but is forced to work as a craftsman on the gigantic studio sets of the time (one of which comes crashing down during filming, with fatal consequences).

As the quasi-Biblical title suggests, West, like so many artists (and censors) of the time, saw modern-day Hollywood as the spiritual successor to Sodom and Gomorrah, and the ending of the film is suitably apocalyptic. As a large crowd gathers for a movie premiere, a small child is nearly killed by a man who has been driven mad by his unrequited love for an aspiring actress. In their fury, the premiere crowd turn on the man and kill him, before destroying everything else in their path. It is one of the most spectacular endings to a “Hollywood on Hollywood” film, exposing the strong emotions (and collective insanity) that cinema can inspire. And the name of the lonely man who is killed by the mob? Homer Simpson. It obviously resonated profoundly with the young Matt Groening, who would resurrect it for his own great screen creation, who would go on to cause endless riots and disturbances.

[youtube https://www.youtube.com/watch?v=ajE9h1zUbMs]

 

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2. The Bad and the Beautiful (Directed by Vincente Minnelli, 1952)

The early 1950s was obviously the golden age of Hollywood films about Hollywood, as The Bad and the Beautiful was released in the same year as Singin’ In The Rain and is another classic of the genre.

One of the many brilliant things that The Bad and the Beautiful does is to show how Hollywood, for all its projection of itself as a place for new talent and new beginnings, is also largely controlled by a few movie dynasties, families of film-makers who exert as much influence as royal families in other countries. The hero (and antihero) of The Bad and the Beautiful is Jonathan Shields, played by Kirk Douglas in one of his first truly great roles, who is the penniless son of a Hollywood tycoon who had squandered the family fortune. In the opening flashback in a film that is really one extended flashback (as Shields’ former collaborators reflect on his mistreatment of them after he has asked them to help him on a new picture), Shields attends his father’s funeral, surrounded by “extras” who he has hired as mourners. It is a wonderful and telling scene, showing how even a penniless man is still capable of putting on a “show,” which he then uses as the launch-pad for his own career in cinema.

The Bad and the Beautiful tells three stories in one: first, how Shields befriends a struggling director and gives him work, until he ultimately betrays him by hiring a “name” director for the film they had both developed together; secondly, how he makes a drunken actress (who is herself the daughter of a famous star, and so, like Shields, “second-generation Hollywood”) a major star; and finally, how he seduces a successful novelist into selling his book to his studio, only to destroy him by turning a blind eye to the genuine seduction of his wife by the film’s star. However, the real story is the oldest story in Hollywood: whatever somebody’s faults, if they can make a movie (and better still a successful, profitable movie), nothing else matters. And that is borne out by the end of the film, when those who Shields had betrayed cannot resist listening for one last time (the three of them gathered round one old-fashioned phone) to see what Shields has come up with for his next movie.

[youtube https://www.youtube.com/watch?v=T4mG-4HBn1w]

 

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1. Sunset Boulevard (Directed by Billy Wilder, 1950)

Sunset Boulevard remains the great grand-daddy of “movies about movies.” Just as the titular road runs through Los Angeles and Beverly Hills, the legendary “home of the stars”, so the film of the same name seems to run through the heart of all films about cinema.

Nearly seventy years after it was made, Sunset Boulevard has itself acquired the kind of mythical status that Wilder identified as the legacy of the original silent movie stars, such as Norma Desmond. Desmond, of course, was immortalised by the glorious Gloria Swanson, who was herself a legend of the “silent screen” who had largely failed to make the transition to “talkies,” making the film at least semi-autobiographical for her.  In fact, the film was at least semi-autobiographical for all the principals. William Holden, who plays the desperate screenwriter Joe Gillis who becomes involved in a mutually exploitative (and ultimately mutually destructive) relationship with Norma, himself hailed originally from the Midwest, as Gillis does; Erich von Stroheim, Norma’s butler who had originally been her husband and director, was once a great film director (as he himself declares, one of the greatest of the silent era) reduced to the status of a jobbing actor; and of course Billy Wilder, the director and co-writer, was originally an Austrian immigrant with poor English who struggled to survive in “movie-town” after fleeing Nazi-dominated Europe. When Joe virtually crashes into Norma’s house when he is fleeing the bailiffs who want to repossess his car, it is tempting to see a little of Wilder himself in the role, fleeing the Nazis who wanted to kill him and every other Jew in Europe.

Sunset is aptly named first because it formally marked the end of the silent era (more than 20 years after it had actually come to an end with the arrival of Al Jolson’s The Jazz Singer), and secondly because it represented a final great flowering of some of the finest talents of that remarkable age, the true dawn of cinema, including Swanson, Von Stroheim and even “old Stoneface” himself, Buster Keaton, who, the film suggests, went from being one of the most famous film stars and directors in the world to just another hand in a game of cards played by the old and almost completely forgotten.

The film itself, of course, is completely unforgettable.

[youtube https://www.youtube.com/watch?v=ADl0wC_cAbk]

 

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Hollywood is one of the greatest centers of artistic production in human history, if not the greatest, and so it is natural that it has itself become one of the archetypal settings of so many modern stories. It has become a kind of modern-day Garden of Eden, in which innocence (in the form of artistic ambition) is forever in conflict with experience (in the form of commercial reality). However, as these great films show, where the original Eden had only one snake, Hollywood is crawling with vipers, in the form of unscrupulous producers, murderous studio execs and insanely ambitious writers and directors. Indeed, the implication of so many of them is: stay long enough and you’ll become a snake yourself, even (or perhaps especially) if you succeed.