Movies like How They Rob Men in Chicago (1900)
The best movies like How They Rob Men in Chicago (1900) are Bottle Rocket (1993), Two-Way Stretch (1960) and The Pickup (2025). If How They Rob Men in Chicago hooked you with its crime and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
How They Rob Men in Chicago
Quick picks
- Highest ratedA Clockwork Orange (1971)8.2/10 from 14,312 votes
- NewestThe Pickup (2025)Released 2025
Bottle Rocket (1993)
Dysfunctional friends Dignan and Anthony plan and execute a robbery with their pot-growing friend, Bob. The short film that inspired Wes Anderson’s feature debut.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisTwo-Way Stretch (1960)
Three criminals plan to break out of prison the day before their release in order to carry out a daring jewel robbery, intending to establish the perfect alibi by returning to jail afterwards. First however they must get out, a task made more difficult by a new, stricter prison officer.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisThe Pickup (2025)
A routine cash pickup takes a wild turn when mismatched armored truck drivers Russell and Travis are ambushed by ruthless criminals led by savvy mastermind Zoe.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisFun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisHow to Rob a Bank (2007)
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisJohnny Dangerously (1984)
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisWelcome to Collinwood (2002)
Five hapless inner-city low-lifes attempt to burgle a pawnbroker's safe, but end up being plagued by bad luck.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisCotton Comes to Harlem (1970)
Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger Jones and Coffin Ed Johnson look into O'Malley's scam, they learn that the cash is being smuggled inside a bale of cotton. However, the police, O'Malley, and lots of others find themselves scrambling when the money goes missing.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisWrong Cops (2013)
A group of bad cops look to dispose of a body that one of them accidentally shot.
Why it matches: Recommended by TMDB viewers · both crime & comedy
Popcorn FlickMovies like thisAfter the Fox (1966)
A criminal mastermind sets up a phony film production as part of a plan to smuggle stolen gold.
Why it matches: Recommended by TMDB viewers · both crime & comedy
Popcorn FlickMovies like thisCa$h (2010)
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both crime & comedy
SnoozefestMovies like thisFlypaper (2011)
A man caught in the middle of two simultaneous robberies at a bank desperately tries to protect the teller with whom he's secretly in love.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like this68 Kill (2017)
Chip's problem is that he can't say no to beautiful women. This weakness gets him into a world of trouble when he agrees to help his girlfriend steal $68,000.
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisDeadpool: No Good Deed (2017)
Deadpool sees an opportunity to save the day, but it doesn't go entirely as planned.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Worth the HypeMovies like thisBandits (2001)
After escaping from prison, Joe and Terry go on a crime spree, robbing banks through Oregon and California in order to finance their scheme for a new life south of the border. Unfortunately, things get more complicated when they meet Kate, who runs into them with her car. She joins the bandits on their cross-country spree, and eventually she steals something, too: their hearts.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisThe Great Train Robbery (1903)
After the train station clerk is assaulted and left bound and gagged, then the departing train and its passengers robbed, a posse goes in hot pursuit of the fleeing bandits.
Why it matches: Recommended by TMDB viewers · both crime
Worth the HypeMovies like thisBlack Caesar (1973)
Raised in Harlem, Tommy Gibbs becomes a successful mob boss but he clashes with the rival Mafia and his old enemy, dirty cop McKinney.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisFoxy Brown (1974)
A voluptuous black woman takes a job as a high-class prostitute in order to get revenge on the mobsters who murdered her boyfriend.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisPolice (1916)
Charlie is released from prison and immediately swindled by a fake parson. A fellow ex-convict convinces Charlie to help burglarize a house.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Protector (1985)
Billy Wong is a New York City cop whose partner is gunned down during a robbery. Billy and his new partner, Danny Garoni, are working security at a fashion show when a wealthy man's daughter, Laura Shapiro, is kidnapped. The Federal authorities suspect that Laura's father is involved with Mr. Ko, a Hong Kong drug kingpin, so the NYC police commissioner sends the two cops to Hong Kong to investigate.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisSnatch (2000)
Unscrupulous boxing promoters, violent bookies, a Russian gangster, incompetent amateur robbers, and supposedly Jewish jewellers fight to track down a priceless stolen diamond.
Why it matches: Similar story and style · both crime & comedy
Worth the HypeMovies like thisIn 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.
Why it matches: Similar story and style · both comedy & crime
Worth the HypeMovies like thisTrouble in Paradise (1932)
Thief Gaston Monescu and pickpocket Lily are partners in crime and love. Working for perfume company executive Mariette Colet, the two crooks decide to combine their criminal talents to rob their employer. Under the alias of Monsieur Laval, Gaston uses his position as Mariette's personal secretary to become closer to her. However, he takes things too far when he actually falls in love with Mariette, and has to choose between her and Lily.
Why it matches: Similar story and style · both comedy & crime
Worth the HypeMovies like thisA Man Walks Into a Bar... (2016)
A man walks into a bar, the start of a bad joke with an even worse pun? or a cautionary tail that tells us, don't tempt fate.........just don't.
Why it matches: Similar story and style · both comedy & crime
The Magic Glass (1914)
A boy uses a professor's liquid to make objects transparent.
Why it matches: Similar story and style · both comedy
Panda Syndrome (2004)
A young boy, Bjørn, discovers on his 17th birthday that his problems with the girls might not be self-inflicted.
Why it matches: Similar story and style · both comedy
Wawa (2008)
Garance has just lost her Wawa. It’s going to be picked up, rolled around, transported, thrown away, carted off, dragged off, snatched up, shot, smashed, trampled, given away, pushed around, stolen, soiled, forgotten, chewed on, slapped, crushed, banged up, and found again. This is the story of the unfortunate trip of a stuffed dog through the streets of Paris.
Why it matches: Similar story and style · both comedy
Antoine and Colette (1962)
After indulging in much delinquency in his youth, seventeen-year-old Antoine Doinel is now an upstanding member of society working for Philips Records, which allows him to indulge in his love of music. At the Youth Concerts, he has noticed the same young woman at several performances. She is Colette, and the two begin to date. Colette treats Antoine like a buddy, while Antoine has fallen in love with her.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisA Clockwork Orange (1971)
In a near-future Britain, young Alexander DeLarge and his pals get their kicks beating and raping anyone they please. When not destroying the lives of others, Alex swoons to the music of Beethoven. The state, eager to crack down on juvenile crime, gives an incarcerated Alex the option to undergo an invasive procedure that'll rob him of all personal agency. In a time when conscience is a commodity, can Alex change his tune?
Why it matches: Similar story and style · both crime
Absolute CinemaMovies like thisA History of Violence (2005)
An average family is thrust into the spotlight after the father commits a seemingly self-defense murder at his diner.
Why it matches: Similar story and style · both crime
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like How They Rob Men in Chicago?
The closest matches to How They Rob Men in Chicago are Bottle Rocket (1993), Two-Way Stretch (1960) and The Pickup (2025). Below are 27 more, each with the reason it matches.
What should I watch after How They Rob Men in Chicago?
Start with Bottle Rocket (1993), the closest match to How They Rob Men in Chicago.
What is the highest-rated movie like How They Rob Men in Chicago?
A Clockwork Orange (1971), rated 8.2/10 by 14,312 TMDB users.
What is the newest movie like How They Rob Men in Chicago?
The Pickup (2025) is the most recent release on this list.
Are there English movies like How They Rob Men in Chicago?
Yes: Bottle Rocket (1993), Two-Way Stretch (1960) and The Pickup (2025).
How are movies similar to How They Rob Men in Chicago chosen?
First come films that Trakt’s viewers watch alongside How They Rob Men in Chicago, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.