Film

Overnight

Overnight is a darkly comic documentary about Troy Duffy, a bartender who sells his screenplay for The Boondock Saints and becomes Hollywood's next wunderkind—only to spectacularly implode. It's a masterclass in hubris, featuring a charismatic subject whose charm curdles into something unsettling as cameras roll. Essential viewing about ambition and entitlement.

TMDb rating3.2

Should you watch it?

Watch it if you like watching an outsize personality charm and bluster his way through Hollywood with a camera rolling, and find human comedy in the gap between confidence and reality.

Skip it if you need a tidy story with a clear hero, since this is untidy, often unflattering to its subject, and its laughs keep brushing against real embarrassment.

What it asks of you: It runs about eighty-two minutes, shot loose and handheld, and asks you to keep track of who is talking and why, more than to follow a plot.

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Spellbound2002

A documentary about competitive spelling that becomes unexpectedly gripping, with charismatic subjects whose personal stakes matter deeply. Captures American ambition and parental pressure with both humour and real sympathy.

But It's essentially about spelling bees, which sounds deathly dull until you're three minutes in and already emotionally invested.

Spellbound poster

The King of Kong: A Fistful of Quarters2007

A documentary that turns arcade gaming into genuine drama, complete with a sympathetic underdog and a villain you'll want to boo. It's funny, weird, and surprisingly touching about obsession and self-made narratives.

But Requires genuine interest in Donkey Kong and 1980s arcade culture, or at least tolerance for that world's dead seriousness.

The King of Kong: A Fistful of Quarters poster

Hoop Dreams1994

A sprawling, humanistic documentary following two basketball prospects over years, capturing systemic exploitation and unfulfilled potential with devastating clarity. One of cinema's best arguments against assuming the documentary form is less demanding than fiction.

But It's three hours long and the trajectory is heartbreaking rather than triumphant, so it requires emotional stamina and patience.

Hoop Dreams poster

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The wildcard

Something you would not have found on your own.

Mulholland Drive2001

Both are obsessed with how Hollywood dreams corrupt and destroy, but where Overnight documents it, Mulholland Drive hallucinates it.

Lynch's fever dream about Hollywood ambition, stardom, and self-delusion shares Overnight's fascination with the machinery that chews people up. But instead of documentary truth, Lynch offers surrealism and dread. Both are about the fantasy versus the reality of becoming a star in LA.

But It's oblique, three hours long, and deliberately opaque—if you want clarity and linear narrative, this will feel like pretentious obstruction.

Mulholland Drive poster
More like this (8)

Tickled2016

Starts as a quirky investigation into competitive tickling and spirals into something genuinely sinister and darkly absurd. You'll never anticipate where it goes, and the filmmaking is clever and propulsive throughout.

But The content involves unsettling power dynamics and emotional manipulation; it's not as light as its premise promises, and some footage is genuinely uncomfortable.

Tickled poster

The Fog of War2003

Errol Morris films Robert McNamara reflecting on his decisions during Vietnam and WWII with devastating intelligence. Hypnotic filmmaking that makes you question the reliability of even sincere self-examination.

But It's essentially one man talking for ninety minutes, and while he's fascinating, his evasions and self-justifications can feel frustrating rather than illuminating.

The Fog of War poster

The Disaster Artist2017

A movie about a movie, exploring how Tommy Wiseau's delusional confidence and ambition created The Room. James Franco captures both the comedy and the pathos of a man utterly committed to his vision despite all evidence.

But If you haven't seen The Room, this will feel like an in-joke you're not in on; it also treats its subject with more warmth than he may deserve.

The Disaster Artist poster

Gates of Heaven1978

Errol Morris's debut about pet cemeteries becomes a profound examination of grief, human connection, and what people choose to preserve. Deceptively strange and genuinely moving.

But It's a pet cemetery documentary, so if you can't get past the inherent weirdness of the subject, nothing Morris does will convince you it matters.

Gates of Heaven poster

Enron: The Smartest Guys in the Room2005

A clear-eyed, elegantly constructed documentary about corporate fraud and hubris that has something to say about American capitalism. Gripping and properly angry without lecturing.

But It's a business documentary about people you likely already dislike, and it doesn't offer much comfort about systemic accountability.

Enron: The Smartest Guys in the Room poster

The Imposter2012

A documentary about Frédéric Bourdin, who convinced a family he was their missing son when he wasn't. Destabilizing and thrilling, playing with documentary form to match its slippery subject.

But It requires you to spend time sympathizing with a con artist, and its playful approach to a real tragedy won't appeal to everyone.

The Imposter poster

Nightcrawler2014

Both are character studies of charismatic narcissists whose smooth confidence masks a complete absence of moral framework, filmed with a kind of admiring fascination.

A narrative thriller about Lou Bloom, a sociopathic climber who exploits Los Angeles chaos for profit. It captures the same unsettling charm, moral vacancy, and self-justification that makes Overnight's subject so magnetic and disturbing.

But Jake Gyllenhaal's performance is deliberately off-putting, and the film takes a dim view of both ambition and those who enable it, offering no heroes.

Nightcrawler poster

The Andy Warhol Diaries2022

Both examine obsessive self-creation and the narcissism required to succeed in America, but Warhol understood artifice as truth, while Duffy simply didn't understand reality at all.

A limited series mixing archival footage, interviews, and stylized recreations to examine Warhol's carefully constructed public persona versus his inner life. Like Overnight, it's interested in how self-invention works and what it costs, but from someone who was actually successful and still felt hollow.

But It's slow and meditative rather than dramatic; if you want a narrative arc with stakes, this is more about mood and surfaces than plot.

The Andy Warhol Diaries poster

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