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Movies like Chicago (2002)

The best movies like Chicago (2002) are The Sting (1973), Bernie (2012) and Cadillac Man (1990). If Chicago hooked you with its comedy and crime, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Sting (1973)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & crime

    Absolute CinemaMovies like this
  2. Bernie (2012)

    In small-town Texas, affable and popular mortician Bernie Tiede strikes up a friendship with Marjorie Nugent, a wealthy widow well known for her sour attitude. When she becomes controlling and abusive, Bernie goes to great lengths to remove himself from her grasp.

    Why it matches: Recommended by TMDB viewers · both comedy & crime

    Popcorn FlickMovies like this
  3. Cadillac Man (1990)

    Joe's a car salesman with a problem—he has two days to sell 12 cars or he loses his job. This would be a difficult task at the best of times but Joe has to contend with his girlfriends (he's two-timing), a missing teenage daughter and an ex-wife.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  4. The Cat's Meow (2002)

    Semi-true story of the Hollywood murder that occurred at a star-studded gathering aboard William Randolph Hearst's yacht in 1924.

    Why it matches: Recommended by TMDB viewers · both drama & crime

  5. Connie and Carla (2004)

    After accidentally witnessing a mafia hit in the Windy City, gal pals Connie and Carla skip town for L.A., where they go way undercover as singers working the city's dinner theater circuit ... disguised as drag queens. Now, it's not enough that they become big hits on the scene; things get extra-weird when Connie meets Jeff -- a guy she'd like to be a woman with.

    Why it matches: Recommended by TMDB viewers · both comedy & crime

  6. Gypsy (1962)

    Gypsy's mother Rose dreams of a life in show business for her daughters, but Louise becomes a huge burlesque star. Stage musical loosely based on the memoirs of Gypsy Rose Lee.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  7. Scarlet Street (1945)

    Cashier and part-time starving artist Christopher Cross is absolutely smitten with the beautiful Kitty March. Kitty plays along, but she's really only interested in Johnny, a two-bit crook. When Kitty and Johnny find out that art dealers are interested in Chris's work, they con him into letting Kitty take credit for the paintings. Cross allows it because he is in love with Kitty, but his love will only let her get away with so much.

    Why it matches: Recommended by TMDB viewers · both drama & crime

    Worth the HypeMovies like this
  8. Just Mercy (2019)

    The powerful true story of Harvard-educated lawyer Bryan Stevenson, who goes to Alabama to defend the disenfranchised and wrongly condemned — including Walter McMillian, a man sentenced to death despite evidence proving his innocence. Bryan fights tirelessly for Walter with the system stacked against them.

    Why it matches: Recommended by TMDB viewers · both drama & crime

    Worth the HypeMovies like this
  9. City Island (2009)

    The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the family, who is a corrections officer in real life, and a hopeful actor in private.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Popcorn FlickMovies like this
  10. Arsenic and Old Lace (1944)

    Mortimer Brewster, a newspaper drama critic, playwright, and author known for his diatribes against marriage, suddenly falls in love and gets married; but when he makes a quick trip home to tell his two maiden aunts, he finds out his aunts' hobby - killing lonely old men and burying them in the cellar!

    Why it matches: Recommended by TMDB viewers · both comedy & crime

    Worth the HypeMovies like this
  11. Unconditional Love (2002)

    After her husband leaves her, a woman travels to London for the funeral of the pop star, Victor Fox, she's adored all her life. There, she meets the lover of the dead pop star, and convinces him to come back to Chicago with her to figure out who killed the singer.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Popcorn FlickMovies like this
  12. Aurora Teagarden Mysteries: Reunited and It Feels So Deadly (2020)

    Aurora's high school reunion turns deadly when a body is found in the hotel pool. Aurora and her Real Murders Club help investigate which classmate was most likely to kill.

    Why it matches: Recommended by TMDB viewers · both crime & drama

    Worth the HypeMovies like this
  13. Bullets Over Broadway (1994)

    After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

    Why it matches: Recommended by TMDB viewers · both comedy & crime

    Worth the HypeMovies like this
  14. See How They Run (2022)

    In the West End of 1950s London, plans for a movie version of a smash-hit play come to an abrupt halt after a pivotal member of the crew is murdered. When world-weary Inspector Stoppard and eager rookie Constable Stalker take on the case, the two find themselves thrown into a puzzling whodunit within the glamorously sordid theater underground, investigating the mysterious homicide at their own peril.

    Why it matches: Recommended by TMDB viewers · both comedy & crime

    Popcorn FlickMovies like this
  15. Kansas City (1996)

    A pair of kidnappings expose the complex power dynamics within the corrupt and unpredictable workings of 1930s Kansas City.

    Why it matches: Recommended by TMDB viewers · both drama & crime

    Popcorn FlickMovies like this
  16. The King of Comedy (1982)

    Aspiring comic Rupert Pupkin attempts to achieve success in show business by stalking his idol, a late night talk-show host who craves his own privacy.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Worth the HypeMovies like this
  17. Dark City (1950)

    War hero Danny Haley fleeces out-of-town dupes in a rigged poker game. He and his pals see Arthur Winant as an easy mark, but they've reckoned without Winant's homicidal brother, who wants revenge after Arthur commits suicide.

    Why it matches: Recommended by TMDB viewers · both drama & crime

    Popcorn FlickMovies like this
  18. Johnny 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 this
  19. Gourmet Detective: A Healthy Place to Die (2015)

    When Henry is invited as a guest speaker at a luxury resort spa, he quickly finds himself at the center of another murder. With Maggie at his side, our favorite duo must not only find the killer but be careful they don't become his latest victim.

    Why it matches: Recommended by TMDB viewers · both drama & crime

    Popcorn FlickMovies like this
  20. The Cable Guy (1996)

    When recently single Steven moves into his new apartment, cable guy Chip comes to hook him up—and doesn't let go. Initially, Chip is just overzealous in his desire to be Steven's pal, but when Steven tries to end the 'friendship', Chip shows his dark side. He begins stalking Steven, who's left to fend for himself because no one else can believe Chip's capable of such behaviour.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  21. Rocky Aur Rani Kii Prem Kahaani (2023)

    Gym-freak brat Rocky falls in love with Rani, who comes from a well-educated Bengali family. Being from polar opposite worlds, the two decide to switch their families to adjust to each other's cultures and backgrounds and to know if their marriage will survive. Rocky and Rani are trapped in a world where they are united by love but divided by families and the ultimate question is will they fit in?

    Why it matches: Similar story and style · both comedy & drama

    Popcorn FlickMovies like this
  22. Not For, or Against (Quite the Contrary) (2003)

    "Ni Pour, Ni Contre" tracks the fall of a young TV camerawoman, Caty, after she becomes involved with a group of petty criminals and their enigmatic leader, Jean. The gang lives hand-to-mouth until the day Jean plans a daring bank robbery. Although other gang members feel out of their league, Jean persuades them to take part and Caty finds herself in a hellish world of betrayal, violence and murder.

    Why it matches: Similar story and style · both drama & crime

    Popcorn FlickMovies like this
  23. Much Ado About Nothing (1993)

    In this Shakespearean farce, Hero and her groom-to-be, Claudio, team up with Claudio's commanding officer, Don Pedro, the week before their wedding to hatch a matchmaking scheme. Their targets are sharp-witted duo Benedick and Beatrice -- a tough task indeed, considering their corresponding distaste for love and each other. Meanwhile, meddling Don John plots to ruin the wedding.

    Why it matches: Similar story and style · both drama & comedy

    Popcorn FlickMovies like this
  24. Frailty (2002)

    A mysterious man arrives at the offices of an FBI agent and recounts his childhood: how his religious fanatic father received visions telling him to kill people who were in fact "demons."

    Why it matches: Similar story and style · both drama & crime

    Worth the HypeMovies like this
  25. Sea of Love (1989)

    Seen-it-all New York detective Frank Keller is unsettled - he has done twenty years on the force and could retire, and he hasn't come to terms with his wife leaving him for a colleague. Joining up with an officer from another part of town to investigate a series of murders linked by the lonely hearts columns he finds he is getting seriously and possibly dangerously involved with Helen, one of the main suspects.

    Why it matches: Similar story and style · both crime & drama

    Popcorn FlickMovies like this
  26. White Chicks (2004)

    Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. To avoid being fired they accept a mission escorting a pair of socialites to the Hamptons--but when the girls are disfigured in a car accident, they refuse to go. Left without options, Marcus and Kevin decide to pose as the sisters, transforming themselves from black men into rich white women.

    Why it matches: Similar story and style · both comedy & crime

    Worth the HypeMovies like this
  27. Home Fries (1998)

    Dorian and Angus chase down their womanizing stepfather with a helicopter, frightening him to death. In his effort to cover their tracks, Dorian begins investigating his stepfather's mistress, Sally. She works at a fast-food drive-through, she's pregnant and Dorian quickly falls in love with her. Unfortunately, his scheming mother wants Sally dead. And Sally isn't sure she wants Dorian to be her child's father and also his brother.

    Why it matches: Similar story and style · both comedy & drama

  28. Death Will Return (1961)

    Adapted from Nikos Foskolos’ theatrical play. On a terribly stormy night, in a secluded hotel, the owner, Brigadier Norton, is murdered. Prime suspects: his daughter Elena, his second wife Liza, Liza’s niece and her fiancé, Norton’s physician, and the hotel staff. Inspector Fox and his assistant, policeman Petridis, are assigned the investigation of the crime. While the suspects’ questioning is under way, some more people arrive at the hotel: detective Tilemachos Christofis with his assistant Aliki, and lieutenant Karalis, a sworn enemy of the victim, complicating things even more.

    Why it matches: Similar story and style · both crime

  29. Les fleurs bleues (2014)

    Why it matches: Similar story and style · both drama

  30. Joe's Apartment (1996)

    A nice guy has just moved to New York and discovers that he must share his run-down apartment with a couple thousand singing, dancing cockroaches.

    Why it matches: Similar story and style · both comedy

Like Chicago and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Chicago?

The closest matches to Chicago are The Sting (1973), Bernie (2012) and Cadillac Man (1990). Below are 27 more, each with the reason it matches.

What should I watch after Chicago?

Start with The Sting (1973), the closest match to Chicago.

What is the highest-rated movie like Chicago?

The Sting (1973), rated 8.0/10 by 3,173 TMDB users.

What is the newest movie like Chicago?

Rocky Aur Rani Kii Prem Kahaani (2023) is the most recent release on this list.

Are there English movies like Chicago?

Yes: The Sting (1973), Bernie (2012) and Cadillac Man (1990).

How are movies similar to Chicago chosen?

First come films that Trakt’s viewers watch alongside Chicago, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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