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Movies that feel like Chicago (2002)

If you loved Chicago, the closest films we have are The Longest Yard (2005), Bad Santa (2003) and Bottle Rocket (1996). All three share Chicago's witty and playful feel, which is what we rank on before quality. 8 of the 12 picks below are included with a subscription right now on Netflix, HBO Max and Amazon Prime Video and others, checked against today's data.

Murderesses Velma Kelly and Roxie Hart find themselves on death row together and fight for the fame that will keep them from the gallows in 1920s Chicago.

🍅 87% Rotten Tomatoes7.2 IMDb ↗TMDB ↗dir. Rob Marshallwittyplayfulgrittycontemplative
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If Chicago hit the spot, these will too

The Longest Yard poster
The Longest Yard
2005 · dir. Peter Segal
🍅 31%6.4drama · comedy · crime

Common ground: prison

The difference: Critics were much harder on this one

Disgraced pro football quarterback Paul Crewe lands in a Texas federal penitentiary, where manipulative Warden Hazen recruits him to advise the institution's football team of prison guards. Crewe suggests a tune-up game which lands him quarterbacking a crew of inmates in a game against the guards. Aided by incarcerated ex-NFL coach and player Nate Scarborough, Crewe and his team must overcome not only the bloodthirstiness of the opposition, but also the corrupt warden trying to fix the game against them.

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Bad Santa poster
Bad Santa
2003 · dir. Terry Zwigoff
🍅 78%7drama · comedy · crime

Witty and playful in the same breath

You'd better watch out - Willie T. Soke is coming to town, and he doesn't care if you've been naughty or nice. Willie's favorite holiday tradition is to fill his sacks with loot lifted from shopping malls across the country. But this year his plot gets derailed by a wisecracking store detective, a sexy bartender, and a kid who's convinced Willie is the real Santa Claus.

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Bottle Rocket poster
Bottle Rocket
1996 · dir. Wes Anderson
🍅 86%6.9comedy · crime · drama

The same mix in both: grit, then stillness

Upon his release from a mental hospital following a nervous breakdown, the directionless Anthony joins his friend Dignan, who seems far less sane than the former. Dignan has hatched a harebrained scheme for an as-yet-unspecified crime spree that somehow involves his former boss, the (supposedly) legendary Mr. Henry.

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The Sting poster
The Sting
1973 · dir. George Roy Hill
🍅 93%8.2comedy · crime · drama

One thread runs through both: chicago, illinois

The difference: 29 years apart, and the 1970s show

A novice con man teams up with an acknowledged master to avenge the murder of a mutual friend by pulling off the ultimate big con and swindling a fortune from a big-time mobster.

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Hustlers poster
Hustlers
2019 · dir. Lorene Scafaria
🍅 88%6.3drama · comedy · crime

Both lean on wit more than on comedy

A crew of savvy former strip club employees band together to turn the tables on their Wall Street clients.

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Hera Pheri poster
Hera Pheri
2000 · dir. Priyadarshan
8.2comedy · crime

Playful crime in both cases

The difference: None of the stillness Chicago is built on

Two tenants and a landlord, in desperate need of money, chance upon a ransom call via a cross connection. They hatch a plan to claim the ransom for themselves.

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Austin Powers in Goldmember poster
Austin Powers in Goldmember
2002 · dir. Jay Roach
🍅 52%6.3comedy · crime

Drama built on grit, twice over

The world's most shagadelic spy continues his fight against Dr. Evil. This time, the diabolical doctor and his clone, Mini-Me, team up with a new foe—'70s kingpin Goldmember. While pursuing the team of villains to stop them from world domination, Austin gets help from his dad and an old girlfriend.

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American Made poster
American Made
2017 · dir. Doug Liman
🍅 85%7.1comedy · crime · drama

Comedy with a pulse of stillness, in both cases

The true story of pilot Barry Seal, who transported contraband for the CIA and the Medellin cartel in the 1980s.

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War Dogs poster
War Dogs
2016 · dir. Todd Phillips
🍅 62%7.1comedy · crime · drama

Witty crime, and it commits to that

Based on the true story of two young men, David Packouz and Efraim Diveroli, who won a $300 million contract from the Pentagon to arm America's allies in Afghanistan.

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Austin Powers: International Man of Mystery poster
🍅 72%7comedy · crime

Both lean on play more than on drama

As a swinging fashion photographer by day and a groovy British superagent by night, Austin Powers is the '60s' most shagadelic spy. But can he stop megalomaniac Dr. Evil after the bald villain freezes himself and unthaws in the '90s? With the help of sexy sidekick Vanessa Kensington, he just might.

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Estômago: A Gastronomic Story poster
Estômago: A Gastronomic Story
2008 · dir. Marcos Jorge
7.8drama · comedy · mystery

Both are built on the same subject: prison

The difference: Leans harder into mystery than Chicago does

In a dog-eat-dog world, Raimundo Nonato has found an alternative way to move ahead: he cooks. No matter what social strata this deceptively innocent young man inhabits, he hones his skills and sharpens his knives—and then he falls in love. Jorge's nimble comic fable provides a smartly constructed gastronomic allegory for ambition and survival.

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Identity Thief poster
Identity Thief
2013 · dir. Seth Gordon
🍅 20%5.7comedy · crime

Comedy with a pulse of grit, in both cases

When a mild-mannered businessman learns his identity has been stolen, he hits the road in an attempt to foil the thief -- a trip that puts him in the path of a deceptively harmless-looking woman.

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The best-reviewed films that share Chicago’s defining feeling.