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Chicago poster

Movies that feel likeChicago (2002)

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.

If you loved Chicago, the closest films we have are A Fish Called Wanda (1988), Bad Santa (2003) and Adaptation. (2002). All three share Chicago's witty and playful feel, which is what we rank on before quality.

Seen the big three already? The under-the-radar pick below is Hera Pheri (2000).

🍅 87% Rotten Tomatoes★ 7.2 IMDb ↗TMDB ↗dir. Rob Marshallwittyplayfulgrittycontemplative
9 of 12 streaming nowParamount Plus Premium · MGM Plus · Sundance Now

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If Chicago hit the spot, these will too

A Fish Called Wanda poster
A Fish Called Wanda
1988 · dir. Charles Crichton
🍅 96%★ 7.5comedy · crime

The same two preoccupations: infidelity, and lawyer

The difference: Trades the stillness of Chicago for an angle of its own

While a diamond advocate attempts to steal a collection of diamonds, troubles arise when he realises he’s not the only one after the collection.

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

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.

Adaptation. poster
Adaptation.
2002 · dir. Spike Jonze
🍅 90%★ 7.6comedy · crime · drama

Both land grit and stillness at once

Charlie Kaufman is a confused L.A. screenwriter overwhelmed by feelings of inadequacy, sexual frustration, self-loathing, and by the screenwriting ambitions of his freeloading twin brother Donald. While struggling to adapt "The Orchid Thief," by Susan Orlean, Kaufman's life spins from pathetic to bizarre. The lives of Kaufman and Orlean's book become strangely intertwined as each one's search for passion collides with the other's.

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

Both lean on wit more than on comedy

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.

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

Crime built on play, twice over

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.

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

Gritty drama in both cases

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.

The Longest Yard poster
The Longest Yard
2005 · dir. Peter Segal
🍅 31%★ 6.4drama · comedy · crimeParamount+Starz

Common ground: prison

The difference: The critics' underdog of the pair

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.

Fun with Dick and Jane poster
Fun with Dick and Jane
2005 · dir. Dean Parisot
🍅 30%★ 6.2comedy · crime

Comedy with a pulse of wit, in both cases

After Dick Harper loses his job at Globodyne in an Enron-esque collapse, he and his wife, Jane, turn to crime in order to handle the massive debt they now face. Two intelligent people, Dick and Jane actually get pretty good at robbing people and even enjoy it – but they have second thoughts when they're reminded that crime can hurt innocent people. When the couple hears that Globodyne boss Jack McCallister actually swindled the company, they plot revenge.

Naked Gun 33⅓: The Final Insult poster
Naked Gun 33⅓: The Final Insult
1994 · dir. Peter Segal
🍅 66%★ 6.5comedy · crimeParamount+

Playful crime, and it commits to that

Frank Drebin is persuaded out of retirement to go undercover in a state prison. There he has to find out what top terrorist, Rocco, has planned for when he escapes. Adding to his problems, Frank's wife, Jane, is desperate for a baby.

Seven Psychopaths poster
Seven Psychopaths
2012 · dir. Martin McDonagh
🍅 82%★ 7.1comedy · crime

One thread runs through both: murder

A struggling screenwriter inadvertently becomes entangled in the Los Angeles criminal underworld after his oddball friends kidnap a gangster's beloved Shih Tzu.

Get Hard poster
Get Hard
2015 · dir. Etan Cohen
🍅 28%★ 6comedy · crimeParamount+

Both are built on the same subject: prison

When millionaire hedge fund manager James is convicted of fraud and sentenced to a stretch in San Quentin, the judge gives him one month to get his affairs in order. Knowing that he won't survive more than a few minutes in prison on his own, James desperately turns to Darnell-- a black businessman who's never even had a parking ticket -- for help. As Darnell puts James through the wringer, both learn that they were wrong about many things, including each other.

Big Momma's House poster
Big Momma's House
2000 · dir. Raja Gosnell
🍅 31%★ 5.3crime · comedyStarz

Different title, same corner of the shelf

When a street-smart FBI agent is sent to Georgia to protect a beautiful single mother and her son from an escaped convict, he is forced to impersonate a crass Southern granny known as Big Momma in order to remain incognito.

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