Top 30 Ranked

Best Crime Movies of 1999, Ranked

Gritty Thrillers and Cult Classics from the End of an Era

Explore the best crime cinema of the year. From heist thrillers to gritty dramas, discover the definitive ranking of late nineties underworld movies.

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About 1999 Crime Movies

As the twentieth century prepared to clock out for the last time, the cinematic landscape of 1999 felt like it was having a collective nervous breakdown. It was a year defined by existential dread, office cubicle rebellions, and a frantic search for authenticity in an increasingly digital world. While science fiction explored the simulated reality of the Matrix, the crime genre dug its heels into the grime of the human psyche, delivering a crop of films that traded traditional police procedurals for something far more jagged and psychological.

To understand the crime movie in 1999, you have to look at how it intersected with the growing cynicism of the era. This was the year of Fight Club, a movie that repurposed the skeletal structure of a crime thriller into a manifesto against consumerism. While the film is often categorized as a drama or a satire, its foundation is built on illegal underground rings, domestic terrorism, and an investigation into a man who does not know himself. It signaled a shift away from the simple morality of the classic detective story toward a narrative where the protagonist was often the greatest threat.

Even the more traditional entries in the genre felt infused with a new sense of stylized urgency. Steven Soderbergh gave us The Limey, a lean and mean revenge story that felt like a love letter to the hardboiled 1960s. By using elliptical editing and fractured timelines, Soderbergh transformed a standard tale of a father seeking vengeance for his daughter into a haunting meditation on memory and regret. It remains a masterclass in how to elevate a pulp premise through pure visual language.

Meanwhile, the heist movie received an injection of high-concept adrenaline with Doug Liman Go. Moving through three different perspectives of a drug deal gone wrong, it captured the frenetic, neon-soaked energy of rave culture. It was crime as a comedy of errors, grounded in the desperation of the working class gig economy before that term even existed. It felt youthful and dangerous in a way that the polished blockbusters of the time simply could not touch.

However, the most enduring achievement of that year might be Anthony Minghella The Talented Mr. Ripley. It reimagined the crime thriller as a lush, sun-drenched nightmare. By focusing on Tom Ripley, a social climber who kills not out of malice but out of a desperate need to belong, the film forced the audience into an uncomfortable alliance with a murderer. It was a sophisticated look at identity theft and class warfare that felt chillingly relevant as the world moved into a new millennium defined by curated personas.

If you look at the landscape of 1999, you see a genre that was no longer satisfied with the binary of the good cop versus the bad criminal. From the gritty underworld of Bringing Out the Dead to the nihilistic obsession of Summer of Sam, the crime films of this vintage were messy and morally complex. They reflected a society that was looking over its shoulder, afraid of what it might find in the rearview mirror. These films did not just provide thrills. They provided a mirror to our own anxieties, proving that the best crime stories are never really about the law, but about the breaking point of the human spirit.

The Complete Rankings

Based on the top picks in drafts on SnakeDrafts

See Top Ten
30
1999 Crime in Two Hands (1999)
Two Hands
1999

19-year-old Jimmy is just scraping by in the red-light district of Sydney. When local crime lord Pando offers him a shot at working for his syndicate, Jimmy jumps at the chance to deliver a costly package. But, when Jimmy gets jacked by a couple of kids, he's indebted to the dangerous gangster for $10,000. Running out of time, he schemes to rob a bank to save himself and a beautiful girl he desires from a gruesome demise.

Comedy
Crime
1h 43m
Gregor Jordan
Heath Ledger, Bryan Brown, Rose Byrne, David Field
29
1999 Crime in Life (1999)
Life
1999

Two men in 1930s Mississippi become friends after being sentenced to life in prison together for a crime they did not commit.

Comedy
Crime
1h 48m
Ted Demme
Eddie Murphy, Martin Lawrence, Obba Babatundé, Nick Cassavetes
28
1999 Crime in Bleeder (1999)
Bleeder
1999

Two stories for the price of one: a video store clerk tries to get acquainted with a waitress; a man beats his pregnant wife, unaware that her brother is a violent racist.

Drama
Crime
1h 37m
Nicolas Winding Refn
Kim Bodnia, Mads Mikkelsen, Rikke Louise Andersson, Liv Corfixen

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27
1999 Crime in The Rifleman of the Voroshilov Regiment (1999)
The Rifleman of the Voroshilov Regiment
1999

A very typical post-Soviet era storyline. A bunch of vagabonds lured an innocent teenage girl to their apartment, offered her a drink, intimidated, then gang raped her. Local cops are incapable to undertake an adequate actions against the scoundrels - prevented by the superior chief of the local police, who is the dad of one of the scumbags. The case is closed. The girl's granddad tired of an endless circumlocution decides to take revenge in his own hands.

Drama
Action
1h 35m
Stanislav Govorukhin
Mikhail Ulyanov, Anna Sinyakina, Aleksandr Porokhovshchikov, Vladislav Galkin
26
1999 Crime in Killer 2 (1999)
Killer 2
1999

Jurek Kiler has become a VIP - sponsoring the Polish government, playing tennis with the President, meeting world leaders. He must oversee a transfer of a substantial amount of gold. However, in his past activities, he has made enemies. Mighty ones. And thus Jurek Kiler's next adventure begins as he has to face attempts at kidnapping, assassinations and problems in his love life...

Comedy
Action
1h 53m
Juliusz Machulski
Cezary Pazura, Janusz Rewiński, Małgorzata Kożuchowska, Katarzyna Figura
25

Tom Ripley is a calculating young man who believes it's better to be a fake somebody than a real nobody. Opportunity knocks in the form of a wealthy U.S. shipbuilder who hires Tom to travel to Italy to bring back his playboy son, Dickie. Ripley worms his way into the idyllic lives of Dickie and his girlfriend, plunging into a daring scheme of duplicity, lies and murder.

Thriller
Crime
2h 20m
Anthony Minghella
24
1999 Crime in Detective Conan: The Last Wizard of the Century (1999)
Detective Conan: The Last Wizard of the Century
1999

Kaitou Kid dares to challenge the police once more, setting his sights on the Russian Imperial Easter Egg. With the date, time, and place, the Osaka police force scrambles to stop him. But this time, Kid may have bitten off more than he can chew—Conan Edogawa, Heiji Hattori, and numerous others are also trying to get their hands on the jeweled egg.

Adventure
Animation
1h 40m
Kenji Kodama
Minami Takayama, Kappei Yamaguchi, Wakana Yamazaki, Akira Kamiya
23
1999 Crime in Running Out of Time (1999)
Running Out of Time
1999

Police inspector and excellent hostage negotiator Ho Sheung-Sang finds himself in over his head when he is pulled into a 72 hour game by a cancer suffering criminal out for vengeance on Hong Kong's organized crime syndicates.

Drama
Action
1h 33m
Johnnie To
Sean Lau Ching-wan, Andy Lau, Yoyo Mung Ka-Wai, Benz Hui Siu-Hung
22
1999 Crime in In China They Eat Dogs (1999)
In China They Eat Dogs
1999

Arvid is an ordinary bank clerk who lives a rather unassuming life with his dear girlfriend. But his life is turned completely upside down when he bravely manages to avert a robbery against the bank where he works.

Action
Comedy
1h 31m
Lasse Spang Olsen
Kim Bodnia, Dejan Čukić, Nikolaj Lie Kaas, Tomas Villum Jensen
21
1999 Crime in Boys Don't Cry (1999)
Boys Don't Cry
1999

A young transgender man explores his gender identity and searches for love in rural Nebraska.

Crime
Drama
1h 58m
Kimberly Peirce
Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III
20
1999 Crime in The Mission (1999)
The Mission
1999

Triad boss Lung, who has just escaped being killed in an assassination attempt hires the killers Curtis, James, Mike, Roy and Shin for his protection.

Action
Crime
1h 24m
Johnnie To
Anthony Wong Chau-Sang, Francis Ng Chun-Yu, Jackie Lui Chung-Yin, Roy Cheung Yiu-Yeung
19
1999 Crime in Bang, Boom, Bang (1999)
Bang, Boom, Bang
1999

Bank robber Kalle Grabowski escapes from prison while his unemployed smalltime crook buddy is sitting around doing nothing after he just lost all their money. A fast paced comedy from German director Peter Thorwarth.

Crime
Action
1h 50m
Peter Thorwarth
Oliver Korittke, Markus Knüfken, Ralf Richter, Diether Krebs
18
1999 Crime in Herod's Law (1999)
Herod's Law
1999

In the 1940s, a small Mexican town has seen its last three mayors assassinated in rapid succession. A naive janitor is recruited to become the new mayor, and he believes he will modernize the little town and usher in a reign of peace. But the system corrupts him very quickly, and he takes to abusing his power while associating with an unscrupulous assortment of opportunists, hypocrites and criminals.

Comedy
Crime
2h 3m
Luis Estrada
Damián Alcázar, Pedro Armendáriz Jr., Isela Vega, Salvador Sánchez
17

A supernatural tale set on death row in a Southern prison, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the cell block's head guard, Paul Edgecomb, recognizes Coffey's miraculous gift, he tries desperately to help stave off the condemned man's execution.

Fantasy
Drama
3h 9m
Frank Darabont
Tom Hanks, David Morse, Bonnie Hunt, Michael Clarke Duncan
16
1999 Crime in The Thomas Crown Affair (1999)
The Thomas Crown Affair
1999

Bored billionaire executive Thomas Crown entertains himself by stealing a Monet from a reputed museum with an elaborate diversion. When Catherine Banning, the insurance company's investigator, takes an interest in Crown, he may have met his match, and a complicated back-and-forth game with seductive undertones begins between them.

Drama
Crime
Pierce Brosnan, Rene Russo, Denis Leary, Frankie Faison
15

Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family," unlucky shrink Dr. Ben Sobel is given just days to resolve Vitti's emotional crisis and turn him into a happy, well-adjusted gangster.

14
1999 Crime in The Corruptor (1999)
The Corruptor
1999

Danny is a young cop partnered with Nick, a seasoned but ethically tainted veteran. As the two try to stop a gang war in Chinatown, Danny relies on Nick but grows increasingly uncomfortable with the way Nick gets things done.

Action
Crime
1h 50m
James Foley
Mark Wahlberg, Chow Yun-Fat, Byron Mann, Kim Chan
13
1999 Crime in Summer of Sam (1999)
Summer of Sam
1999

Spike Lee's take on the "Son of Sam" murders in New York City during the summer of 1977 centering on the residents of an Italian-American Northeast Bronx neighborhood who live in fear and distrust of one another.

Crime
Drama
2h 22m
12
1999 Crime in Arlington Road (1999)
Arlington Road
1999

Bedraggled college professor Michael Faraday has been vexed — and increasingly paranoid — since his wife's accidental death in a botched FBI operation. When a seemingly all-American couple set up house next door, Michael begins to suspect there’s more to them than meets the eye.

Crime
Drama
1h 57m
Mark Pellington
11
1999 Crime in Double Jeopardy (1999)
Double Jeopardy
1999

Libby Parsons, wrongly convicted of her husband Nick's murder, thinks he is still alive. She survives the long years in prison with two burning desires sustaining her -- finding her son and solving the mystery that destroyed her once-happy life. Standing between her and her quest, however, is her parole officer, Travis Lehman. Libby poses a challenge to the cynical officer, one that forces him to face up to his own failings while pitting him against his superior and law enforcement colleagues, as she plunges into a desperate fight for justice, survival, and revenge.

Thriller
Crime
1h 45m
Bruce Beresford
Ashley Judd, Tommy Lee Jones, Bruce Greenwood, Annabeth Gish
10
1999 Crime in The Bone Collector (1999)
The Bone Collector
1999

Lincoln Rhyme was the department's top homicide detective and leading expert in criminal forensics until an injury left him paralyzed, depressed, and incapable of working. But when a gruesome murder in Manhattan leaves detectives baffled, they call on Rhyme to help solve the mystery. Amelia Donaghy, a rookie cop whose quick thinking preserved a gruesome murder scene, is enlisted by Rhyme to be his on-the-scene forensics expert. With Amelia reluctantly acting as Rhyme's able-bodied go-between, the pair piece together cryptic clues the killer leaves behind at the scene of the crime, hoping to catch the grisly serial killer.

Crime
Thriller
1h 58m
Phillip Noyce
Why it ranks

The film revitalizes the serial killer subgenre by grounding its investigative thrills in heavy atmosphere and forensic minutiae. Its strength lies in the interplay between paralyzed intellect and street-level intuition, creating a claustrophobic race against a meticulously cruel antagonist.

9

When the body of Army Capt. Elisabeth Campbell is found on a Georgia military base, two investigators, Warrant Officers Paul Brenner and Sara Sunhill, are ordered to solve her murder. What they uncover is anything but clear-cut. Unseemly details emerge about Campbell's life, leading to allegations of a possible military coverup of her death and the involvement of her father, Lt. Gen. Joseph Campbell.

Thriller
Mystery
1h 56m
Simon West
Why it ranks

This somber procedural peels back the layered secrecy of military life to reveal a haunting intersection of power and gender politics. It operates with a cold, formal precision that emphasizes the institutional barriers often protecting the guilty.

8
1999 Crime in Blue Streak (1999)
Blue Streak
1999

Miles Logan is a jewel thief who just hit the big time by stealing a huge diamond. However, after two years in jail, he comes to find out that he hid the diamond in a police building that was being built at the time of the robbery. In an attempt to regain his diamond, he poses as an LAPD detective.

Action
Comedy
1h 33m
Les Mayfield
Martin Lawrence, Luke Wilson, Dave Chappelle, Peter Greene
Why it ranks

By subverting the heist genre with high-energy physical comedy, this feature succeeds through the sheer charismatic friction of a criminal masquerading as a cop. It finds its edge in the kinetic, improvised absurdity of its lead, turning a standard undercover trope into a fast-paced romp.

7
1999 Crime in True Crime (1999)
True Crime
1999

Boozer, skirt chaser, careless father. You could create your own list of reporter Steve Everett's faults but there's no time. A San Quentin Death Row prisoner is slated to die at midnight – a man Everett has suddenly realized is innocent.

Crime
Thriller
Clint Eastwood, Isaiah Washington, LisaGay Hamilton, James Woods
Why it ranks

Clint Eastwood explores the moral ticking clock of the American penal system with a weathered, investigative cynicism. The film eschews bombast in favor of a weary, low-stakes tension that highlights the systemic rot within judicial bureaucracy.

6
1999 Crime in Ghost Dog: The Way of the Samurai (1999)
Ghost Dog: The Way of the Samurai
1999

A Black hitman who models after the samurai of old finds himself targeted for death by the mob.

Crime
Drama
Forest Whitaker, John Tormey, Cliff Gorman, Frank Minucci
Why it ranks

Jim Jarmusch crafts a meditative collision between ancient bushido codes and modern mob dynamics that feels entirely singular. Forest Whitaker’s stoic performance anchors a hip-hop-infused fable where silence and philosophy are just as lethal as any firearm.

5
1999 Crime in 8MM (1999)
8MM
1999

A small, seemingly innocuous plastic reel of film leads surveillance specialist Tom Welles down an increasingly dark and frightening path. With the help of the streetwise Max, he relentlessly follows a bizarre trail of evidence to determine the fate of a complete stranger. As his work turns into obsession, he drifts farther and farther away from his wife, family and simple life as a small-town PI.

Thriller
Crime
2h 3m
Joel Schumacher
Why it ranks

Joel Schumacher plunges into the pitch-black abyss of the snuff film underworld, crafting an unsettling journey that interrogates the viewer's own voyeurism. The suffocating atmosphere and industrial grime provide a visceral, uncomfortable texture that few mainstream thrillers dare to inhabit.

4
1999 Crime in Payback (1999)
Payback
1999

With friends like these, who needs enemies? That's the question bad guy Porter is left asking after his wife and partner steal his heist money and leave him for dead -- or so they think. Five months and an endless reservoir of bitterness later, Porter's partners and the crooked cops on his tail learn how bad payback can be.

Action
Drama
1h 40m
Brian Helgeland
Mel Gibson, Gregg Henry, Maria Bello, David Paymer
Why it ranks

Lean and ruthlessly efficient, this throwback to seventies grit strips away modern artifice to deliver a cold-blooded study in professional persistence. Its monochromatic aesthetic and unrelenting focus on a singular, stubborn objective make it a purist's delight.

3
1999 Crime in Go (1999)
1999

A supermarket clerk decides to step in for an absent drug dealer, setting off an explosive, comedic chain of events.

Crime
Comedy
1h 42m
Doug Liman
Sarah Polley, Timothy Olyphant, Katie Holmes, Desmond Askew
Why it ranks

This propulsive, non-linear descent into the Los Angeles underground pulses with the frantic energy of a stimulant-fueled weekend. It serves as a vibrant time capsule of rave culture, weaving together disparate criminal threads with a sharp, cynical wit.

2
1999 Crime in The Limey (1999)
The Limey
1999

The Limey follows Wilson, a tough English ex-con who travels to Los Angeles to avenge his daughter's death. Upon arrival, Wilson goes to task battling Valentine and an army of L.A.'s toughest criminals, hoping to find clues and piece together what happened. After surviving a near-death beating, getting thrown from a building and being chased down a dangerous mountain road, the Englishman decides to dole out some bodily harm of his own.

Crime
Drama
Terence Stamp, Lesley Ann Warren, Luis Guzmán, Barry Newman
Why it ranks

Steven Soderbergh delivers a masterful exercise in fractured memory and hard-boiled vengeance, anchored by Terence Stamp’s hypnotic screen presence. The film’s rhythmic editing elevates a standard retribution premise into a sophisticated, impressionistic piece of neo-noir art.

1
1999 Crime in The Boondock Saints (1999)
The Boondock Saints
1999

Tired of the crime overrunning the streets of Boston, Irish Catholic twin brothers Conner and Murphy are inspired by their faith to cleanse their hometown of evil with their own brand of zealous vigilante justice. As they hunt down and kill one notorious gangster after another, they become controversial folk heroes in the community. But Paul Smecker, an eccentric FBI agent, is fast closing in on their blood-soaked trail.

Action
Thriller
1h 48m
Troy Duffy
Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco
Why it ranks

A hyper-kinetic explosion of vigilante justice, this cult phenomenon redefined the brotherhood dynamic through stylized gunplay and a subversive, religious zealotry. Its frantic pacing and irreverent spirit capture a specific late-nineties independent grit that remains unmatched in its audacity.

FAQ

Frequently Asked Questions

Everything you need to know about this list and SnakeDrafts

The 1999 crime movies on this list often explore themes like vengeance, moral ambiguity, and the complexity of justice. Films such as 'The Limey' and 'True Crime' delve into personal quests for truth, while others like 'The Boondock Saints' and 'Payback' focus on vigilante justice and retribution.

Crime comedies such as 'Go' and 'Blue Streak' incorporate humor and fast-paced storytelling, offering a lighter, energetic take on criminal escapades. In contrast, darker crime dramas like '8MM' and 'The Bone Collector' present gritty, intense narratives centered on mystery and human psychology.

Directors like Steven Soderbergh ('The Limey'), Joel Schumacher ('8MM'), and Clint Eastwood ('True Crime') made notable impacts by blending crime with thriller and mystery elements. Jim Jarmusch's work on 'Ghost Dog: The Way of the Samurai' also stands out for its unique fusion of crime and philosophical drama.

'Go' is celebrated for its interwoven storytelling and energetic pace, which was innovative in crime comedies. 'Ghost Dog: The Way of the Samurai' blends samurai code with modern gangster life, creating a distinctive cinematic style that sets it apart in the genre.

Both '8MM' and 'The Bone Collector' delve into the psychological horror and mystery surrounding criminal acts, highlighting the disturbing depths of human nature. Their intense atmospheres and focus on uncovering hidden truths exemplify the grim, suspenseful side of 1999 crime films.

Suspense and mystery are critical, especially in films like 'Double Jeopardy,' 'The General's Daughter,' and 'True Crime,' where plot twists and investigative elements drive the narratives. These aspects heighten viewer engagement, making the unraveling of crimes central to the storytelling.

Action sequences in 'Payback' and 'The Corruptor' complement their crime-driven plots by intensifying confrontations and raising the stakes. These films blend gritty crime narrative with thrilling physicality, enhancing the adrenaline and dramatic impact typical of late 90s crime cinema.
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