The darkest depictions of Hollywood in film

Lana Del Rey’s “Hollywood sadcore” was born out of a very specific vision of LA’s glitzy celebrity centre. The vision depicted in sordid detail by Kenneth Anger and Norman Mailer: cult leaders and poolside ennui, ostrich feather trim and strung-out sex symbols, all against a sparkling backdrop of palm trees and the Chateau Marmont. Del Rey herself plays the sort of tragic starlet Marilyn Monroe came to embody, describing tar black souls and poisoned minds in the same breath as her outfit. This particular Hollywood hasn’t existed since the ‘50s and ‘60s, but it’s the one everyone pictures when they say “dark Hollywood.”

This juxtaposition of rot and glamour is, perhaps, what draws us to Hollywood movies purporting to expose the seedy underbelly of Hollywood. It’s addictive and aesthetically pleasing — I am consuming this neon pipe dream of sex and stardom but it’s okay because they acknowledge how fucked up it is and this permits me to find its fucked-uppedness sexy. After all, these movies are still multi-million dollar, executive produced, money-making spectacles selling a very romantic, faux-ironic view of grit. They feature household names or rising stars as has-beens and never-will-bes. But despite (or because of) the self-indulgent cynicism required in watching such films, we can’t seem to look away. Here are ten of Hollywood’s darkest self-portraits.

MULHOLLAND DR. (2001)

One critic’s description of this film as a “poisonous valentine to Hollywood” couldn’t be more apt. This is the ultimate Hollywood horror. David Lynch takes the cliché of “bumfuck-defected ingénue loses her innocence to become a star” and turns it into a very bad trip. It starts off coherent enough, with Naomi Watts playing aforementioned ingénue and Laura Harring as a sultry amnesiac. Then the disorientation sets in and we’re in peak Black Lodge weirdness: Previously established plot points dissolve entirely, people play other people, time gets pulled through a taffy machine and chopped up into little pieces. Aesthetic: dread creeping over the Hollywood sign until it fills the entire sky.

MAPS TO THE STARS (2014)

This is probably the least David Cronenberg-esque movie of David Cronenberg’s career. But stripped of his signature body horror and techno-surrealism, it actually might be the darkest, most cynical film in an oeuvre of dark, cynical films. It also may be his funniest, thanks to a script by novelist and screenwriter Bruce Wagner. This satire follows a brood of royally screwed up people suffocated by their abusive families: An unstable aging starlet who can’t compare to her dead, far more talented mother (Julianne Moore doing an amazing Lindsay Lohan impression), a child star fresh out of rehab, and his exploitative, fame-obsessed parents. About the film, Cronenberg said, "Hollywood is a world that is seductive and repellent at the same time, and it is the combination of the two that makes it so potent.” And also savagely quotable.

SUNSET BOULEVARD (1950)

This is the #1 Hollywood self-critique, although it focuses less on the industry’s corruption than its debilitating effect on its former cash cows. Set mostly in a rotting mansion and opening with a murderous nod to The Great Gatsby, this film follows a sleazy screenwriter (William Holden) who tries to use forgotten film-star Norma Desmond (Gloria Swanson) as a back-door to fame. While Mulholland Dr. immerses the viewer in its descent to madness, Sunset Boulevard forces us to watch a sad, grotesque timelapse of a woman drowning in delusion. This would actually make a great double-feature with Requiem for a Dream, and by great I mean utterly miserable.

WHATEVER HAPPENED TO BABY JANE? (1962)

Like Sunset Boulevard, this is not so much about Hollywood itself as how it can fuck you up for a very long time. The main character’s backstories seem like a PSA for the unpredictable cruelty of child stardom: Baby Jane Hudson (Bette Davis) has achieved fame as a peroxide Shirley Temple, leaving her sister Blanche (Joan Crawford) in the dust. But then Blanche succeeds as an actress, while Baby Jane flops into alcoholism. Decades later, both have been forgotten, Baby Jane keeping a paralyzed Blanche captive and tormenting her in their mansion. This is a nasty, claustrophobic, anxiety-inducing look at people who peaked too soon, and how Hollywood enables them to keep playing those memories over and over again.

THE CANYONS (2013)

This movie has been dragged for filth, and for good reason. But its unrelenting, porn-filter sleaze makes it far more effective than films like Starry Eyes, which try to convey Hollywood’s shittinesss via hackneyed Faustian metaphors. It follows the tawdry, malaise-flecked lives of failed-actress-turned-sugar-baby Tara (Lindsay Lohan) and her abusive film financer boyfriend Christian (James Deen). Given the long list of sexual assault accusations against him, Deen’s sociopathic performance comes off as a little too precise and makes it uncomfortable to watch in retrospect. But the film is more self-aware and self-deprecating than most people give it credit for (Lohan’s pitch-perfect casting and the involvement of Bret Easton Ellis providing obvious clues). It’s not the “visually and tonally precise, acid-etched horror story of souls wandering through a hyper-materialist hell” described by one critic, but it’s fun to watch in all its non-stop ugliness.

THE NEON DEMON (2016)

Like The Canyons, people really don’t give this movie enough credit for self-awareness, and a lot of moviegoers seemed to have missed its rather scathing humour. While it’s about the model, not movie industry of Hollywood, it still builds upon the familiar set-up of a Midwestern nobody becoming somebody seen in Mulholland Dr. Elle Fanning stars as a preternaturally beautiful model who becomes a coveted fetish from almost everyone in the industry, except for a pair of jealous, deadpanning models played by Abbey Lee and Bella Heathcote. Since it’s directed by Nicolas Winding Refn, it looks like a giallo perfume ad and involves cannibalism and necrophilia.

BARTON FINK (1991)

The Coen Brothers take a handful of Hollywood tropes and combine them into a twisted, phantasmagoric, heavily symbolic takedown of the film and stage industries’ huge egos. In one of the most unsettling depictions of writer’s block, pretentious New York playwright Barton Fink (John Tuturro) holes himself up in a Shining-esque hotel in Hollywood to write the script for a wrestling film, but can’t. Like Mulholland Dr., he soon finds himself stuck in what seems to be an endless bad trip, albeit a much funnier one (for the audience). This is a cathartic film both for narcissistic, condescending writers who talk more about writing than they actually write, and the people who have to deal with them.

THE DAY OF THE LOCUST (1975)

This film isn’t the kind of witty, self-satisfied satire that shows up elsewhere on this list, but it just as brutally condemns Hollywood life. Instead of rising stars or aging legends, this uber-depressing gothic follows a group of Tinseltown bottom-feeders swarming over each other to be exploited. The story of industry losers is rarely told in other dark Hollywood films, and director John Schlesinger gives it the Diane Arbus/John Waters treatment it deserves. Although set in the ‘30s, The Day of the Locust gives off major apocalypse vibes, with omens showing up throughout the film and culminating in the hellish finale. This is for people who like their Hollywood with a side of nightmare fuel.

S.O.B. (1981)

Despite its plot involving four failed suicide attempts and a pornographic remake of a musical, this one is actually the feel-good movie on the list. Like Death Becomes Her and Tropic Thunder, S.O.B. uses its misanthropy and over-the-top shenanigans to make fun of safe targets—filthy rich film producers and actresses who don’t exactly inspire much sympathy in their quest to become even more rich and famous. Mirroring director Blake Edwards’ and wife Julie Andrews’ attempts to rebrand Maria from the Sound of Music as a femme fatale, it revolves around a fictional producer (Richard Mulligan) who convinces his wife (played by Andrews) to go topless in a softcore adaptation of his last flop, because he just couldn’t deal with failure. At times, it comes off as an industry inside joke accidentally made public to the unwashed masses, but it’s so caustic and funny it doesn’t really matter.