Movies like Sky in Diamonds (1999)
The best movies like Sky in Diamonds (1999) are Fun with Dick and Jane (1977), Ca$h (2010) and Simpsley (2026). If Sky in Diamonds hooked you with its comedy and crime, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRaising Arizona (1987)7.1/10 from 2,462 votes
- NewestSimpsley (2026)Released 2026
Fun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisCa$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 thisSimpsley (2026)
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment: Skinner's clingy, dim-witted mooch of a houseguest, Homer Simpsley. Lies, lust and Italian lira are abound.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Absolute CinemaMovies like thisDead Man's Bluff (2005)
Sergei and Simon have to deliver a suitcase full of heroin to Mikhalych or else they will be killed. There is one minor detail: the only problem-solving technique they are familiar with is a shot in the head.
Why it matches: Recommended by TMDB viewers · both crime & comedy
Popcorn FlickMovies like thisOne Night at McCool's (2001)
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Why it matches: Recommended by TMDB viewers · both comedy & crime
SnoozefestMovies like thisPsycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
Why it matches: Recommended by TMDB viewers · both crime & comedy
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 thisRaising Arizona (1987)
When a childless couple—an ex-con and an ex-cop—take one of a wealthy family’s quintuplets to raise as their own, their lives grow more complicated than anticipated.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Worth the HypeMovies like thisVIP Cop: New Year's Eve Mayhem (2018)
On the eve of the new year, the Barvikha Severnoe police station is threatened with closure. To save his own department, a police officer from Rublyovka Grisha Izmailov is forced to go to extreme measures and, together with operatives, decides to rob a bank. He is counting on the fact that his colleagues, together with the head of the department, Yakovlev, will easily disclose this matter, the money will be returned back, and everyone will keep their work next year. But everything is not going the way Grisha planned ...
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisThe Pope of Greenwich Village (1984)
Charlie and his troublesome cousin Paulie decide to steal $150,000 in order to back a "sure thing" race horse that Paulie has inside information on. The aftermath of the robbery gets them into serious trouble with the local Mafia boss and the corrupt New York City police department.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisMarried to the Mob (1988)
Angela de Marco is fed up with her gangster husband's line of work and wants no part of the crime world. When her husband is killed for having an affair with the mistress of mob boss Tony "The Tiger" Russo, Angela and her son depart for New York City to make a fresh start. Unfortunately, Tony has set his sights upon Angela -- and so has an undercover FBI agent looking to use her to bust Tony.
Why it matches: Recommended by TMDB viewers · both comedy & crime
Popcorn FlickMovies like thisThere's Good Weather in Deribasovskaya, Or It's Raining Again in Brighton Beach (1993)
When mysterious Russian bandit named Artist came in USA, brave Russian special agent Fyodor Sokolov runs to States for defeat evil master.
Why it matches: Recommended by TMDB viewers · both crime & comedy
SnoozefestMovies like thisTrap House (2025)
An undercover DEA agent and his partner embark on a game of cat and mouse with an audacious, and surprising group of thieves – their own rebellious teenagers, who have begun robbing from a dangerous cartel, using their parents' tactics and top-secret intel to do it.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisThe Last Days of American Crime (2020)
In the not-too-distant future, as a final response to crime and terrorism, the U.S. government plans to broadcast a signal that will make it impossible for anyone to knowingly break the law.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisMisdirection (2026)
A desperate couple have pulled off a string of high-end break-ins to pay off a mob debt. When they attempt to rob their latest victim, they find themselves caught in a deadly game of cat and mouse. The tables are turned and the hunters become the hunted.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like thisThe System (2022)
When a young soldier, newly returned from war, gets caught up in a drug bust, he is recruited by the authorities to go undercover in a notoriously dangerous prison in order to figure out what is really going on.
Why it matches: Recommended by TMDB viewers · both crime
Worth the HypeMovies like thisIn the Blood (2014)
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisWhat a Mess! (1995)
A Russian criminal steals a giant diamond from the Mafia, hides it, and suddenly runs into his unknown brothers; unexpected, absurd events with participation of the mob, doctors, musicians, Americans, militia, and gypsies ensue.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisUntil Death (2007)
Anthony Stowe is a dirty cop who is hooked on heroin—and everyone hates him. After a serious accident, he is placed into an induced coma, but emerges from it a better person who wants to put things right.
Why it matches: Recommended by TMDB viewers · both crime
SnoozefestMovies like thisCode 8 Part II (2024)
In a world where superpowered people are heavily policed by robots, an ex-con teams up with a drug lord he despises to protect a teen from a corrupt cop.
Why it matches: Recommended by TMDB viewers · both crime
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Sky in Diamonds?
The closest matches to Sky in Diamonds are Fun with Dick and Jane (1977), Ca$h (2010) and Simpsley (2026). Below are 17 more, each with the reason it matches.
What should I watch after Sky in Diamonds?
Start with Fun with Dick and Jane (1977), the closest match to Sky in Diamonds.
What is the highest-rated movie like Sky in Diamonds?
Raising Arizona (1987), rated 7.1/10 by 2,462 TMDB users.
What is the newest movie like Sky in Diamonds?
Simpsley (2026) is the most recent release on this list.
How are movies similar to Sky in Diamonds chosen?
First come films that Trakt’s viewers watch alongside Sky in Diamonds, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.